Gallic acid

Gallic acid

IUPAC name[hide]
3,4,5-trihydroxybenzoic acid
Other names[hide]
Gallic acid
Gallate
3,4,5-trihydroxybenzoate

CAS number
PubChem
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Jmol-3D images

Identifiers
149-91-7 , [5995-86-8]
(Monohydrate)
370
361
632XD903SP
C01424
CHEBI:30778
CHEMBL288114
Image 1
SMILES

[show]
InChI
[show]
Molecular formula
Molar mass
Appearance
Density
Melting point

Solubility in water
Acidity (pKa)

Properties
C7H6O5
170.12 g/mol
White, yellowish-white, or
pale fawn-colored crystals.
1.7 g/cm3 (anhydrous)
250 C, 523 K, 482 F
1.1 g/100 ml water @ 20C
(anhydrous)
1.5 g/100 ml water @ 20 C
(monohydrate)
COOH: 4.5, OH: 10.

Hazards
MSDS
External MSDS
Main hazards
Irritant
Related compounds
Related compounds
Benzoic acid, Phenol, Pyrogallol
(verify) (what is: / ?)
Except where noted otherwise, data are given for materials in
their standard state (at 25 C, 100 kPa)
Infobox references

Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, a type of organic acid, also
known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak
bark, and other plants.[1] The chemical formula is C6H2(OH)3COOH. Gallic acid is found both
free and as part of tannins.
Salts and esters of gallic acid are termed 'gallates'. Despite its name, it does not contain
gallium.
Gallic acid is commonly used in the pharmaceutical industry.[2] It is used as a standard for
determining the phenol content of various analytes by the Folin-Ciocalteau assay; results are
reported in gallic acid equivalents.[3] Gallic acid can also be used as a starting material in the
synthesis of the psychedelic alkaloid mescaline.[4]
Gallic acid seems to have anti-fungal and anti-viral properties. Gallic acid acts as an
antioxidant and helps to protect human cells against oxidative damage. Gallic acid was found
to show cytotoxicity against cancer cells, without harming healthy cells. Gallic acid is used as
a remote astringent in cases of internal haemorrhage. Gallic acid is also used to treat
albuminuria and diabetes. Some ointments to treat psoriasis and external haemorrhoids
contain gallic acid.[5]

Historical context and uses

Gallic acid is an important component of iron gall ink, the standard European writing and
drawing ink from the 12th to 19th century with a history extending to the Roman empire and
the Dead Sea Scrolls. Pliny the Elder (23-79 AD) describes his experiments with it and writes
that it was used to produce dyes. Galls (also known as oak apples) from oak trees were
crushed and mixed with water, producing tannic acid (a macromolecular complex containing
gallic acid). It could then be mixed with green vitriol (ferrous sulfate) obtained by
allowing sulfate-saturated water from a spring or mine drainage to evaporate and gum
arabic from acacia trees; this combination of ingredients produced the ink.[6]
Gallic acid was one of the substances used by Angelo Mai (17821854), among other early
investigators of palimpsests, to clear the top layer of text off and reveal hidden manuscripts
underneath. Mai was the first to employ it, but did so "with a heavy hand", often rendering
manuscripts too damaged for subsequent study by other researchers.[citation needed]

Gallic acid was discovered by French chemist and pharmacist Henri Braconnot (17801855)
in 1818, and studied by French chemist Thophile-Jules Pelouze (18071867).
Early photographers, including Joseph Bancroft Reade (18011870) and William Fox Talbot
(18001877), used gallic acid for developing latent images in calotypes. It has also been used
as a coating agent in zincography.
George Washington used gallic acid to communicate with spies[clarification needed] during the
American Revolutionary War, according to the miniseries America: The Story of Us.[citation
needed]

Gallic acid is a component of some pyrotechnic whistle mixtures.

Natural occurrence
Gallic acid is found in a number of land plants. It is also found in the aquatic plant
Myriophyllum spicatum and shows an allelopathic effect on the growth of the blue-green alga
Microcystis aeruginosa.[7]

List of plants that contain the chemical

Gallic acid is found in oaks species like the North American white oak (Quercus alba)
and European red oak (Quercus robur).[8]

Caesalpinia mimosoides[9]

Drosera (sundew)

Rhodiola rosea (Golden root)

Triphala (Ayurvedic herbal rasayana formula)

Toona sinensis

Asam galat
Dari Wikipedia bahasa Indonesia, ensiklopedia bebas
Belum Diperiksa
Langsung ke: navigasi, cari

Asam Galat

Nama IUPAC[sembunyikan]
3,4,5-trihydroxybenzoic acid
Nama lain[sembunyikan]
Gallic acid
Gallate
3,4,5-trihydroxybenzoate
Identifikasi
Nomor CAS
PubChem
SMILES

[149-91-7]
370
Oc1cc(cc(O)c1O)C(O)=O

Sifat
Rumus molekul
Massa molar
Penampilan
Densitas
Titik lebur
Kelarutan dalam air
Keasaman (pKa)
MSDS
Bahaya utama
Senyawa terkait

C7H6O5
170.12 g/mol
Putih, putih-kekuningan atau
kristal berwarna coklat-kekuningan
pucat.
1.7 g/cm3 (anhidrat)
1.1 g/100 ml air @ 20 C (anhidrat)
1.5 g/100 ml air @ 20 C (anhidrat)
COOH: 4.5, OH: 10.
Bahaya
External MSDS
Irritant
Senyawa terkait
Asam benzoat, Fenol, Pirogallol

Kecuali dinyatakan sebaliknya, data di atas berlaku

pada temperatur dan tekanan standar (25C, 100 kPa)
Sangkalan dan referensi

Asam galat adalah senyawa golongan asam fenolik C6-C1 (en:phenolic acid} atau
hidroksibenzoat, yaitu asam 3,4,5-trihidroksibenzoat.[1] Asal kata galat adalah kata galle
dalam bahasa Prancis yang berarti pembengkakan pada jaringan tanaman setelah terserang
serangga parasit.[2] Senyawa ini dapat ditemukan pada daun ek dan anggur dan memiliki
aktivitas sebagai antioksidan (penangkal radikal bebas).[2][3] Asam galat adalah subunit dari
galotanin, yaitu polimer heterogen yang mengandung berbagai molekul asam galat yang
saling terkait dengan asam galat lain serta dengan sukrosa dan gula lainnya.[1] Banyak
galotanin yang menghambat pertumbuhan tanaman karena dapat merombak enzim sitoplasma
dengan cara mendenaturasi protein (enzim adalah protein), dan ketahanan tumbuhan yang
mengandungnya kemungkinan disebabkan karena galatonin diangkut ke vakuola sehingga
terpisah dari enzim di sitoplasma.[1]

Biosintesis
Asam galat merupakan senyawa turunan asam sinamat yang pembentukkannya melalui
lintasan asam sikimat dengan bahan dasar asam 3-dehidrosikimat[2] Reaksi penting dalam
pembentukan asam sinamat dan berbagai turunannya adalah pengubahan fenilalanin menjadi
asam sinamat melalui proses deaminasi atau pelepasan amonia dari fenilalanin untuk
membentuk asam sinamat.[1] Reaksi ini dikaalisis oleh enzim fenilalanin amonia liase.
Berikutnya asam sinamat diubah menjadi p-kumarat dengan penambahan satu atom oksigen
dari O2 dan atom H dari NADPH langsung pada posisi para dari asam sinamat (posisi atom
karbon keempat dihitung dari gugus asam sinamat pada cincin benzena).[1] Penambahan lagi
gugus hidroksil (OH) lainnya di sebelah gugus OH dari asama p-kumarat dengan reaksi
serupa menghasilkan asam kafeat.[1] Penambahan gugus metil (-CH3) dari S-adenosil
metionin (SAM) e gugus OH dari asam kafeat menghasilkan asam ferulat.[1] Asam kafeat
membentuk ester dengan gugus alkohol dalam asam lainnya yang terbentuk pada lintasan
asam sikimat, yaitu asam quinat, dan menghasilkan asam klorogenat. [1]
Berikut ini adalah gambar-gambar senyawa asam sinamat dan turunannya

Asam sinamat

Asam p-kumarat

Asam kafeat

Asam ferulat


Asam quinat

Asam klorogenat

Asam protokatekuat

Asam galat

Lihat pula

Antioksidan

Galotanin

Referensi
1.

^ a b c d e f g h Salisbury FB, Ross CW. 1995. Fisiologi Tumbuhan, Jilid 2.

penerjemah: Lukman DR, Sumaryono. Bandung:Penerbit ITB. Hal:145-147. ISBN
979-8591-27-5

2.

^ a b c (Inggris)Crozier A, Clifford MN, Ashihara H. 2006. Plant Secondary

Metabolites: Occurrence, Structure and Role in the Human Diet. Oxford: Blackwell
Publishing Ltd. Hal: 11-16, 244-249. ISBN-13: 978-1-4051-2509-3

3.

^ Golumbic C, Mattill HA. 2007. The antioxidant properties of gallic acid and
allied compounds. J of the American Oil Chemists' Society 19(8):144-145.

http://id.wikipedia.org/wiki/Asam_galat

GALLIC ACID, A NATURAL ANTIOXIDANT, IN AQUEOUS

AND MICELLAR ENVIRONMENT: SPECTROSCOPIC STUDIES
KRZYSZTOF POLEWSKI, SEBASTIAN KNIAT, DANUTA SLAWINSKA
Institute of Physics, August Cieszkowski Agricultural University, PoznaN Poland

The spectroscopic properties of gallic acid (GA) and their modification with ionization
state in aqueous and micellar environment have been studied. Results show that GA
absorbance and fluorescence maxima are pH dependent. It is shown by the shift of the
absorbance maximum from 272 nm at pH 2.8 to 260 nm at pH 7. These results are
accompanied by fluorescence changes in the intensity, red shift of the position of the
emission maximum, shape of the spectrum and quantum yield. Observed changes
indicate on the existence of two forms of GA resulting from the proton dissociation at
COOH group: neutral form which exists below apparent pKa at 3.4 and anionic form
above that pH. To develop a basis for monitoring the interactions of GA with biological
compound its absorption and fluorescence properties in heterogeneous and nonpolar
media has been studied. No significant partition under physiological conditions was
observed. The binding of GA anion to cationic micelle was observed which occurred by
electrostatic interaction. In protic solvents GA molecules form very efficiently hydrogen
bonds which strongly influence its spectroscopic properties. In low polarity and nonprotic solvents GA fluorescence is characterized by enhance in the fluorescence quantum
yield and a blue shift in the emission maximum, however, in dioxane its behavior is
closer to those observed in protic solvents. In view of the role played by antioxidant
properties of some food, including red wine, and some natural drugs these results are
relevant to future studies of GA in those materials during its action to fulfill its protective
role.
INTRODUCTION

Gallic acid (GA), 3,4,5-trihydroxybenzoic acid, Fig. 1, and its derivatives are biologically
active compounds which are widely present in plants (Kahkonen, Hopia, Vourela, Rauha,
Philaja, Kujala & Heinonen, 1999; Lee, Lee, Park, Toh, Lee, Jang & Kim, 2000). The
chemical and biochemical properties of GA are well described in the literature. According
to these references GA is a strong natural antioxidant (Aruoma, Murcie, Butler &
Halliwell, 1993, Heinonen, Lehtonen & Hopia, 1998, Khan, Ahmad & Hadi, 2000, Zheng &
Wang, 2001). It is able to scavenge hypochlorous acid at a rate sufficient to protect
1 antiproteinase against inactivation by this molecule. GA decreases the peroxidation
of ox brain phospholipids (Milic, Djilas & Canadovic-Brunet, 1998). Free radicals have
been implicated in the etiology and pathogenesis of numerous disease states including
cardiovascular disease, cancer and diabetes (Inoue, Suzuki, Sakaguchi, Li, Takeda,
Ogihara, Jiang & Chen, 1995; Sakagami, Satoh, Hatano, Yoshida & Okuda, 1997; Aoki,
Ishiwata, Sakagami, Kusama & Katayama, 2001). Free radicals occur as a natural
consequence of cell metabolism. They are also produced as results of oxidative stress
(Schmidt, Traenckner, Meier & Baeuerle, 1995; Koga, Moro, Nakamori, Yamakoshi,
Hosoyama, Kataoka & Ariga, 1999, Terasaka, Tamura, Takayama, Kashimata, Ohtomo,
Machino, Fujisawa, Toguchi, Kanda, Kunii, Kusama, Ishino, Watanabe, Satoh, Takano,
Takahama & Sakagami, 2000). Antioxidant capacity of gallate esters against hydroxyl,
azide, and superoxide radicals has also been reported (Masaki, Atsumi & Sakurai, 1995;
Satoh, Ida, Sakagami, Tanaka & Fujisawa, 1998; Bors & Michel, 1999; Pulido, Bravo &
Saura-Calixto, 2000; Metelitza, Eryomin, Sviridov & Kamyshnikov, 2001). GA is
widespread in plant foods and beverages such as tea and wine and was proven to be one
of the anticarcinogenic polyphenols present in green tea (Ho, Chen, Shi, Zhang & Rosen,
1992; Kerry & Abbey, 1997; Abu-Amsha Caccetta, Burke, Mori, Beilin, Puddey & Croft,
2001; Landrault, Poucheret, Ravel, Gasc, Cros & Teissedre, 2001). The consumption in
France of a diet high in saturated fat coupled with an apparently low incidence of
coronary heart disease (referred to as the "french Paradox") has been associated with
the consumption of red wine (Landrault et al., 2001). Antioxidants present in red wine
have been shown to have a protective role against oxidation of LDL in vitro (Arce, Rios &
Volcarcel, 1998). GA is a strong chelating agent and forms complexes of high stability
with iron (III) (Sroka, Rzadkowska- Bodalska & Mazol, 1994, Li, Bandy, Tsang &
Davison, 2000). It has shown phytotoxity and antifungal activity against Fusarium
semitectum, F. fusiformis and Alternaria altternata (Dowd, Duvick & Rood, 1997). GA is
of great interest in arteriosclerosis prevention (Abella & Chalas, 1977)

Fig. 1. Chemical structure of a) gallic acid; b) anion of gallic acid

The spectral properties of GA

as reflected by the absorption
and fluorescence spectra
received a little attention. In
view of the multiple roles
played by GA in medicine and
food sciences its fluorescence
could be a convenient tool to
study the processes where GA
is involved. Our results show
that GA fluorescence as
measured by its intensity,
emission and quantum yield is
pH dependent.
These results are further
supported by absorbance
changes with pH. In biological
milieu GA interacts in
heterogeneous environment

where its reaction rate,

reactivity, conformation and
spectral properties may
significantly differ from those
observed in aqueous,
homogeneous solutions. We
thus investigated the
fluorescence characteristics in
nonpolar and micellar
environments to enable us to
mimic the changes that could
take place in GA fluorescence
during its action in
heterogeneous environment.

In this paper we have characterized the spectroscopic properties (absorption and

fluorescence) and their modulation with the ionization state of GA molecules in aqueous
and heterogeneous environment.
MATERIALS AND METHODS
Materials
Gallic acid, propyl gallate and pyrogallol were from Fluka (FLUKA AG, Germany), sodium
dodecyl sulphate-(SDS), tetradodecyltrimethylammonium bromide- (TTABr), -cyclodextrin, glycerine and acrylamide were purchased from Sigma Chemicals (SIGMA Co,
New Orleans).
Organic solvents were from Merck. (MERCK Co., USA) The buffer used in the range of pH
from 3 to 9.4 was sodium ammonium-acetate. The pH value from 2 to 3 was adjusted by
adding appropriate volumes of 0.1 M HCl to aqueous sample.
All samples were prepared daily and were measured directly after mixing all
components.
Methods
The absorption spectra from 200 nm were taken with SD 1000 spectrophotometer from
Avantes (Netherlands) in 1 cm quartz cuvette. The fluorescence spectra were measured
in 1cm path-length quartz cuvette with a Shimadzu RF 5001 PC spectrofluorimeter
(Shimadzu, Japan) and were then corrected using correction kit from Shimadzu. The
spectra were taken at room temperature, 210 C.
The samples were excited at 270 nm which is in the range of isosbestic point to avoid
complications with fluorescence intensity determination caused by different absorbances
of two forms of GA.
In order to determine the partition coefficients of GA between phases in micellar
environment, the obtained spectra were decomposed by fitting procedure using the least
square method into appropriate components representing aqueous phase and micellar
phase. The partition coefficient was calculated as the ratio of the area of micellar phase
component to total area of the spectrum.

The fluorescence quantum yield was determined as described in Lakowicz (1983). As a

fluorescence quantum yield standard tryptophan with = 0.13 was used Eftink (1991).
The quantum-mechanical calculations have been carried out with the programs from
HyperChem package from HyperCube (Ontario, Canada). For geometry optimization and
electron density distribution semi-empirical method PM3 with CI was applied.
RESULTS
Absorption spectra
In aqueous solution the absorption spectrum of gallic acid (GA) exhibits two peaks in the
UV range. One at 225 nm with molar extinction coefficient = 26500 (M1 cm1) and
the other at 260 nm with = 21200 (M1 cm1). In buffered solutions the higher
energy peak is located between 227 nm and 230 nm. The lowest energy peak shows
maximum between 257 nm to 269 nm. The absorption spectra of GA in buffer at pH 2.5
and pH 6 are shown in the inset in Fig. 2. Their exact position depends on the ionization
state of GA molecule. The shifts of absorption maximum position of the GA in buffered
ammonium-acetate solutions at different pH are shown in Fig. 2.

Fig. 2. The shifts of the position of absorption maximum of the 5 10-6 M

GA in buffered ammonium-acetate solutions (closed circles) and in 30 mM
TTABr (closed squares) recorded at different pH. The inset shows the
absorption spectra of 5 10-6 M gallic acid at pH 2.5 (curve 1) and at pH
5.4 (curve 2).

In acidic solutions the absorbance

maximum is located at 269 nm.
Increasing pH gradually shifts the
maximum to 257 nm with sharp
change in position at pH 3.5. In the
range from pH 4.5 to 7.5 the shift of
maximum is small. Further increase
of the samples pH above 7 leads to
the formation of a new, additional
peak with maximum at 295 nm.
Those results indicate that in
buffered solutions may exist different
GA forms caused by ionization of the
GA molecule. Bellow pH 3.4 we may
expect the existence of a neutral
form of GA (Ia), with its absorbance
maximum at 269 nm. In the range of
slightly acidic and neutral pH we
observe the anionic form of GA (Ib)
characterized by the absorption
maximum at 257 nm. At basic pH
care must be taken because GA
undergoes fast autooxidation what
leads to colorization of the solution
which is non-fluorescent. The other
peak with maximum at 225 nm at pH
2 gradually shifts to 231 nm at pH 7.

In the presence of the anionic detergent SDS, nonionic detergent TRITON X-100 and cyclo dextrin of the buffered solutions of GA the absorption spectra are similar to those
observed in aqueous solutions, which indicates that interactions of the above chemicals
with GA do not affect its absorption spectra.

The presence of the cationic detergent, TTABr, in GA buffered solutions induces changes
in the absorption spectra compared to buffer-only solutions, Fig. 2. At pH 2.7 we observe
the shift of maximum to 271 nm. Steeper slope in the pH range from 2.5 to 6 gives
higher pKa values compared to buffer solution. It looks like the presence of the cationic
micelle stabilizes the position of absorbance at 257 nm from pH 5 up to pH 7.5 compared
to buffer-only where the position continually changes with pH. At pH above 8 the
presence of micelle slows down the autooxidation of GA compared to buffer solution only.
The apparent pKa value derived from Fig. 2 calculated for the changes observed for the
lowest energy peak equals 3.34 compared to pKa value equal to 3.13 reported in
literature by Bykova, Petrov and Blagodatskava (1970). In TTABr micelles calculated
pKa1= 4.3 what indicates that the presence of cationic detergent changes the
protonation equilibrium of GA forms.

In order to determine the nature of

the observed interactions the
absorption spectra of GA were taken in
organic solvents with different
dielectric constant and different protic
character. The spectral properties of
GA in different solvents are collected
in Table 1.

Fig. 3. The shifts of the position of emission maximum of the 5 10-6 M GA

in buffered ammonium-acetate solutions and in 30 mM TTABr recorded at
different pH. Excitation at 270 nm. The assignment of the curves is given
in the Legend.

The absorption maxima of the peaks

in organic solvents are red shifted
compared to that in water. Only in
0.1% DMSO solution the maximum is
shifted to 256 nm. The positions of the
maximum do not depend on the
dielectric constant of the solvent and
its permanent dipole moment. In
dioxane, the solvent with the lowest
dielectric constant, 2.2, the maximum
is shifted to 268 nm compared to 260
nm in water, in alcohols to 271 nm
and to 267 nm for acetonitrile, a
nonprotic solvent with dielectric
constant close to that of methanol.
Such results indicate that we observe
specific interactions that in case of GA
lead very probably to formation of
efficient hydrogen bonding with
solvent in protic solvents.

Fluorescence spectra
Whereas the apparent ionization process and hydrogen bonding formation detected by
absorption changes may reflect the behavior of GA only in ground state, the fluorescence
of GA will provide information of GA behavior in excited state.
During our experiments the intrinsic fluorescence of GA acid was used to study its
behavior in different conditions. Figure 3 shows the change in GA fluorescence maximum
position with pH in buffer and micellar solution. In buffer solution the emission maximum
of GA changes very fast from 368 nm at pH 2 to 346 nm at pH 3.5 then remains steady
up to pH 5. Simultaneously the increase in intensity is observed. The increase in

fluorescence intensity is not connected with absorbance changes observed for GA

molecules at different pH thus is mostly due to higher quantum yields of the ionized
forms of GA compared to that of the neutral form which is very weakly fluorescent.
Calculations show that the fluorescence quantum yield of GA increases from 0.004 at pH
2.5 to 0.01 at pH 7.
The observed shift of the maximum above pH 6 is accompanied by a change in the shape
of spectrum, which results from the appearance of the new shoulder with maximum at
414 nm observedin the spectrum above pH 4. At higher pH values, above 8, in the
presence of air, fast autooxidation of GA occurs what excludes any further measurements
using stationary techniques. The presented above fluorescence data also confirm the
existence of the two forms of GA. One, neutral form, (Ia), with emission maximum at
368 nm and another, anionic form, (Ib), with emission maximum at 347 nm. Apparent
pKa = 2.4 calculated from Fig. 3 is much lower than that obtained from absorbance data.
This indicates that in the lowest excited state GA molecule becomes more acidic then in
ground state. These changes are related to the changes in charge distribution between
the ground and excited states.

In excited state of the GA

molecule there should be a
substantial decrease of electron
density at carboxylic hydroxy
oxygen atom leading to
deprotonation at lower pH than in
buffer. The dielectric
microenvironment experienced by
GA during its biological action
would be significantly lower than in
the bulk aqueous phase thus we
investigated the fluorescence
properties of GA in environments
of lower polarity and different
protic properties. Because above
Fig. 4. Emission spectra of 5 10-6 M GA obtained in buffer at pH 5.4 (1) and 30
mM TTABr (2). Excitation at 270 nm. Curve 3 is the difference between spectrum pH 3.2 GA is a negatively charged
2 and spectrum 1.
molecule we also checked how it
binds and partitions with positively
charged micelles.
In neutral micelle TRITON X-100,
DMSO and anionic micelles, SDS,
no changes in fluorescence spectra
of GA compared to buffered
solutions were noticed except that
for the last one the inten sities are
lower by about 20%.

In

-cyclo dextrin small changes in

position, 1 nm of red shift, and the
emission intensity, 2%, were
observed.
In the presence of cationic micelle
TTABr some significant changes in
fluorescence spectra of GA are
observed. The fluorescence intensities
of GA in the presence of micelle are at
least two times higher compared to
aqueous solutions. The positions of
the fluorescence maxima are shifted
with increasing pH of the solution
what is shown in Figure 3. It shows
that in all pH range the maximum
emission is blue shifted compared to
the maximum observed in buffered
solution. Calculated apparent pKa is
about 4 compared to 2.4 found in
buffered only solution. In micellar
environment the process of
autooxidation is shifted toward higher
pH compared to buffered solution.

Fig. 5. Fluorescence intensity of 5 10-6 M GA in glycerin at its maximum

recorded versus water content. Excitation at 270 nm

It suggests that the presence of micelles protect, to a certain degree, GA molecules from
autooxidation.
Above pH 4 in the presence of TTABr micelles the new peak at 396 nm appears. The
emission spectrum in TTABr is superposition of two peaks.
One peak is characteristic for the GA molecules in buffer with maximum at 347 nm. The
other peak located at 397 nm, reflects the GA molecules interacting with the micellar
environment. Examples of the emission spectra of GA in buffer and in TTABr at pH 6 are
presented in Fig. 4. After subtraction the new spectrum with maximum at 405 nm is
revealed. It seems obvious that this peak represents that part of GA anions, which
interact with cationic micelle and this band will be used to determine the partition of GA
molecules between phases.
In all organic solvents used different intensity changes and different shifts of the
fluorescence maximum compared to that in water are observed.
The positions of the peaks, fluorescence quantum yields and Stokes shifts are collected
in Table 1. In dioxane and in acetonitrile the emission maximum is located at 335 nm, in
diethyl ether at 329 nm. In methanol, ethanol and propanol the peak maxima are
located around 362 nm and in water the maximum is located at 339 nm. The fact that
the two solvents like methanol, protic, and acetonitrile, non-protic, with similar dielectric
constants exhibit difference between positions of maxima and distinct intensities
indicates that in protic and non-protic solvents two different types of interaction
mechanisms occur. Additionally, in the investigated alcohols the spectral properties of GA
are very similar, see Table 1. Lower fluorescence intensities, red shift of the peak
positions and similar positions of the maxima of GA observed in the presence of protic
solvents, like alcohols, indicates on a very probable formation of hydrogen bonds
between GA and solvent. The fact that GA in water exhibits spectral properties, except

intensity, which are closer to protic solvents, than to alcohols is an indication that GA
molecule in aqueous solutions exists as hydrated molecule. In dioxane GA shows
maximum at 335 nm characteristic for non-protic solvents but it shows rather low
quantum efficiency comparable with the other protic solvents. It may come from the fact
that dioxane is able to form hydrogen bonds and despite its low dielectric constant
behaves as a protic solvent (Schmitke et al., 1997). In non-protic solvents the observed
increasing quantum yield,

Table 1. Spectral and physico-chemical properties of gallic acid (GA) in different solvents. Dielectric constant, dipole
moment D, abosrbance and emission maxima nm, fluorescence quantum yield and Stokes shift cm-1.

Data for dielectric constants and dipole moments taken from P.W. Atkins, Physical Chemistry, ed. Freeman, New York,
1985

higher energy of emission and lower Stokes shift indicate that excited energy is
dissipated to surrounding less efficient then in polar solvents.
The lack of any additional band in non-protic solvent in absorbance spectra excludes the
formation of ground state complex. In excited state the formation of new entity, like
excimer or dimer and GA molecule may occur. Especially, that GA molecule is prone to
form such dimer because of the presence of carboxylic moiety in its structure.
That carboxylic moiety is bearing donor function of OH group and acceptor function of
C=O group.
Therefore they may form very stable hydrogen bonded dimers, especially in nonprotic
solvents.
However, the data presented in Table 1, like blue shift and higher quantum yield
compared to protic solvents, indicates that emission occur from monomeric forms of GA
molecules. This indicates on the van der Waals interactions between excited GA
molecules and solvent molecules.
The absorption and emission spectra of GA in glycerin and glycerin-water mixtures were
taken in order to explore the influence of viscosity on the observed phenomena. The plot

of fluorescence intensity at its maximum versus water content is given in Fig. 5. The
sudden drop of the fluorescence intensity when water is added to the system is
observed. This confirms again that hydrogen bond formation is the main phenomenon in
protic solvents, which is responsible for the spectroscopic properties of GA.
The observed intensity increase, spectral shift and newly formed peak indicates that in
the presence of cationic detergent occur some interactions which lead to partition of GA
forms between aqueous and micellar phases. Because the hydrophilic character of GA
molecule prevents it from entering micellar interior, the main force responsible for the
observed spectrum is an electrostatic interaction between charged micelle and GA anion.
Fluorescence quenching and partition studies
In order to estimate how GA molecules are distributed between micellar and aqueous
phase we used the spectra, which characterize GA in aqueous solutions, peak at 347 nm,
and micellar solutions, peak at 405 nm. The method was described in the Methods
section. Calculated area under that band divided by the area of the whole spectrum
recorded in micellar phase gave the partition coefficient.
Obtained that way values indicate that at pH 4.2 about 70% of GA molecules interact
with micellar environment. This partition is slowly decreasing with pH and starting from
pH 5.4 it remains constant at 50% up to pH 7. Taking into account the fact that the
micelle concentration at given condition is two orders of magnitude higher than
concentration of GA molecules, this behavior may reflect the process connected with
concentration equilibrium between excited GA anions and available cationic micelles.

Fig. 6. Emission intensity of 5 10-6 M GA observed at 405 nm

versus TTABr micelle concentration at pH 5.4. Excitation at 270 nm.

To explain this problem we observed

the behavior of GA emission
recorded at 405 nm with increasing
concentration of TTABr micelle. The
results are presented in Fig. 6. At
low concentration of TTABr, bellow
1.5 mM, the GA fluorescence is
quenched. Above 1.5 mM the
emission intensity shows sharp
increase what arises from the
interactions between single molecule
of TTABr and GA. Above 7 mM TTABr,
close to critical micelle concentration
(cmc) literature value for that
detergent (Womack, Kendall &
MacDonald, 1983), the emission
increases much slower compared to
the premicellar concentrations of the
detergent. This comes from the fact
that in micelles the existence of so
called Stern layer, where up to 70%
of counterions reside, may repulse
part of the anionic GA molecules.

Quenching studies were carried out to determine the localization of GA molecules and
determine how GA molecules interact with micelles. The results are presented as the
Stern-Volmer plot in Fig. 7. It shows the data for GA in solution at pH 6 in the presence
of detergent and without. The fluorescence intensities are monitored at 347 nm and 405

nm, which describe the GA molecules in aqueous and micellar phase respectively. In
buffer solutions and in the presence of detergent, the plots are straight lines with larger
slope in micellar environment. The calculated quenching constant vary from KSV = 16.7
M1 in buffer to KSV = 19.2
M1 (at 347 nm in micelle) and 48 M1 (at 405 nm) in TTABr. Those results indicate that
quencher has equal access to GA molecules in bulk phase in both environments. In
micellar environment more efficient quenching occurs. This indicates that GA molecule
definitely is not embedded into micellar interior and quenching is the result of the
electrostatic interactions between charged GA anion, cationic micelle TTABr and a
quencher. The higher quenching constant of GA in micelle may come from the fact that
electrostatic interaction between quencher ion with cationic micelle changes the
concentration homogeneity of quencher molecules around micelle. This causes that more
fluorophores are adjacent to a quencher at the moment of excitation and the
deactivation process is more efficient.
Quantum-mechanical calculations

Using PM3 semi-empirical

method we calculated the
distribution of electron density
for ground and few lowest
excited states for neutral and
ionic forms of GA. Those
calculations show that electron
density distribution in ground
state are mainly located on the
aromatic ring and oxygen O
atoms of hydroxyl groups
attached to the aromatic ring.

Fig. 7. Stern-Volmer plots of 5 106 M GA emission quenched by acrylamide in

buffered solution at pH 5.4 and with added 30 mM detergent TTABr. Excitation
at 270 nm. Data are taken at 368 nm in buffer and 405 nm in TTABr. The
assignment of the curves is given in the Legend.

In the lowest excited states the

electron density is still mainly
located on aromatic ring
however some of electronic
charge is shifted to the
carboxylic moiety. The
calculation also have shown that
GA molecule in neutral and
anionic form in the ground state
may form five to eight hydrogen
bonds with water molecules.
Distribution of electron density
on the flexible groups, especially
when connected through
hydrogen bonds to surrounding
environment, forms many paths
to deexcite GA molecule and
may explain observed low
fluorescence quantum yield in
protic solvents.

These calculations confirm our conclusions based on the experimental results that in
protic solvent GA molecule exists as a highly hydrated molecule.

DISCUSSION
The presented results show that GA absorbance and fluorescence (intensity, emission
maximum and shape) depend on the pH of the solvent. The apparent pKa values of GA
obtained from our experiments are close to pKa1=3.13 and pKa2=8.45 as reported by
Bykova et al. (1970). An examination of chemical structure of GA shows that there are
two ionizable moieties in the GA molecule: the carboxylic group and three phenolic
hydroxyl groups. The first pKa value for that molecule is connected with ionization at
carboxylic group. At basic pH, above pH 8.5, the observed maximum at 295 nm is very
probably associated with ionization of the proton of 8-hydroxy group because 5-OH
group has very high pKa due to efficient intramolecular H bonding. Such coincidence
found for the pKa values clearly indicates that observed changes are not due to solely
excited-state processes but rather are connected with ionization state of the GA molecule
where neutral and anionic forms are present. The effect of micelles on the protonation
equilibrium of GA can be explained on the basis of the pseudophase ion exchange model
(Romsted & Zanette, 1988). In terms of this model, the shifts in pKa values, compared
to buffer solution, is caused by transfer of GA monoanion into cationic surface of TTABr.
This leads to new the neutral-monoanion equilibrium at higher pH.
In the lowest excited state GA molecule undergoes dissociation at lower pH, 2.7, what
indicates on the charge decrease on the oxygen atom in OH group in carboxylic moiety.
In micelle in the excited state the new neutral-monoanion equilibrium at pKa = 4 is
established which is close to that in ground state, 4.5. This indicates that interaction
between micelle and GA molecules is independent on protic properties of solvent and this
driving force is an electrostatic interaction.
Absorption spectrum of pyrogallol, a compound that has structure similar to GA except is
devoid of carboxylic group, do not exhibit any shift in water and organic solvents and its
absorbance maximum positions are similar to that observed for GA. For propyl gallate,
derivative of GA with carboxyl group replaced by propyl group, the absorption maximum
in water is shifted to 269 nm. This data suggest that hydrogen bonding interactions is
the main interaction in protic solvents and that absorption spectrum is subject to change
when significant changes in the electronic distribution in the GA molecule occurs, i.e. like
a new, more hydrophobic propyl moiety is attached.
The variation of fluorescence quantum yield of GA with pH can be further interpreted by
use of the rotamer model based on the quantummechanical calculation. According to this
model this process may be rationalized in terms of electrostatic repulsion between
deprotonated oxygen from carboxylic group and -electrons from aromatic ring. In case
of neutral form, at pH<pKa1, such interactions are much weaker and whole group may
rotate freely then dissipation of excitation energy is very efficient and yield of
fluorescence is very low. At pH>pKa1 but lower than pKa2 GA will exist predominantly as
anion. This is due to stabilization gained from the energetically favorable electrostatic
interactions between negatively charged hydroxyl oxygen from carboxylic group and electrons from aromatic ring. Thus the molecule becomes more rigid and fluorescence
quantum yield increases. This model calculated for the molecule in vacuum is probably
correct for neutral form of GA, where quantum yield is indeed very low. In protic solvents
where efficient hydration of GA molecule occurs the steric hindrance is canceled by the
attached solvents molecules what efficiently dissipate excitation energy and even for
anionic form the fluorescence quantum yield is low.
Incubation of GA acid with DODAB membranes, data not shown, -cyclodextrin and
micelles did not result in appreciable partitioning or binding, as evidenced by a lack of
change of fluorescence maximum, quantum yield and quenching.

The inability of GA to bind to the membrane and micelles could be attributed to its
insufficient hydrophobicity.
In physiological conditions interactions between molecules occur in the dielectric
microenvironment which is different then aqueous and additionally depend on the
hydrophobic nature of the molecule. The obtained results indicate that the binding of GA
to involves some type of specific polar interactions. The fact that neutral GA molecule
does not interact with cationic micelle whereas anionic GA molecules interact with
cationic micelle easily indicates on electrostatic forces as a main mechanism responsible
for that phenomenon.
The results of spectroscopic studies reported here indicate that GA molecule may exert
its biological role by combining its electrostatic and hydrogen bonding properties
according to actual microenvironment.
Acknowledgmen
This work was supported by grant DS 508/82-2 from the Agricultural University of
Pozna, Poland. The authors wish to thank to Mr Piotr Rolewski for a great technical
assistance during measurements.

GALLIC ACID
MSDS Number: G0806 --- Effective Date: 10/29/01

1. Product Identification
Synonyms: 3,4,5-Trihydroxybenzoic acid, monohydrate; gallic acid, monohydrate
CAS No.: 149-91-7 (Anhydrous) 5995-86-8 (Monohydrate)
Molecular Weight: 188.14
Chemical Formula: C6H2(OH)3COOH.H2O
Product Codes: J.T. Baker: M685
Mallinckrodt: 3112

2. Composition/Information on
Ingredients

IngredientCASNo
PercentHazardous

GallicAcid149917
100%Yes

3. Hazards Identification
Emergency Overview
-------------------------CAUTION! MAY CAUSE IRRITATION TO SKIN, EYES, AND RESPIRATORY
TRACT.
J.T. Baker SAF-T-DATA(tm) Ratings (Provided here for your convenience)
----------------------------------------------------------------------------------------------------------Health Rating: 1 - Slight
Flammability Rating: 1 - Slight
Reactivity Rating: 0 - None
Contact Rating: 1 - Slight
Lab Protective Equip: GOGGLES; LAB COAT
Storage Color Code: Orange (General Storage)
----------------------------------------------------------------------------------------------------------Potential Health Effects
---------------------------------There is insufficient data in the published literature to perform a complete hazard evaluation
for this product.
Special precautions must be used in storage, use and handling. Protective equipment should
be chosen using professional judgment.
Inhalation:

May cause irritation to respiratory tract resulting in coughing and sneezing.

Ingestion:
Low systemic toxicity. Large amounts may cause some gastrointestinal discomfort, nausea or
diarrhea.
Skin Contact:
May cause irritation to the skin with redness or minor inflammation on moist skin.
Eye Contact:
May cause eye irritation due to possible temporary abrasiveness. Can cause redness, tearing
and possibly some pain.
Chronic Exposure:
No information found.
Aggravation of Pre-existing Conditions:
No adverse health effects expected.

4. First Aid Measures

Inhalation:
Remove to fresh air. Get medical attention for any breathing difficulty.
Ingestion:
Give several glasses of water to drink to dilute. If large amounts were swallowed, get medical
advice.
Skin Contact:
Wash exposed area with soap and water. Get medical advice if irritation develops.
Eye Contact:
Wash eyes with plenty of water for at least 15 minutes. Call a physician.

5. Fire Fighting Measures

Fire:
As with most organic solids, fire is possible at elevated temperatures or by contact with an
ignition source.
Explosion:
Not considered to be an explosion hazard.
Fire Extinguishing Media:
Water spray, dry chemical, alcohol foam, or carbon dioxide.
Special Information:
In the event of a fire, wear full protective clothing and NIOSH-approved self-contained
breathing apparatus with full facepiece operated in the pressure demand or other positive
pressure mode.

6. Accidental Release Measures

Remove all sources of ignition. Ventilate area of leak or spill. Wear appropriate personal
protective equipment as specified in Section 8. Spills: Sweep up and containerize for
reclamation or disposal. Vacuuming or wet sweeping may be used to avoid dust dispersal.

7. Handling and Storage

Keep in a tightly closed container, stored in a cool, dry, ventilated area. Protect against
physical damage. Protect from light. Containers of this material may be hazardous when
empty since they retain product residues (dust, solids); observe all warnings and precautions
listed for the product.

8. Exposure Controls/Personal
Protection
Airborne Exposure Limits:
None established.
Ventilation System:

A system of local and/or general exhaust is recommended to keep employee exposures as low
as possible. Local exhaust ventilation is generally preferred because it can control the
emissions of the contaminant at its source, preventing dispersion of it into the general work
area. Please refer to the ACGIH document, Industrial Ventilation, A Manual of Recommended
Practices, most recent edition, for details.
Personal Respirators (NIOSH Approved):
For conditions of use where exposure to dust or mist is apparent and engineering controls are
not feasible, a particulate respirator (NIOSH type N95 or better filters) may be worn. If oil
particles (e.g. lubricants, cutting fluids, glycerine, etc.) are present, use a NIOSH type R or P
filter. For emergencies or instances where the exposure levels are not known, use a full-face
positive-pressure, air-supplied respirator. WARNING:
Air-purifying respirators do not protect workers in oxygen-deficient atmospheres.
Skin Protection:
Wear protective gloves and clean body-covering clothing.
Eye Protection:
Use chemical safety goggles. Maintain eye wash fountain and quick-drench facilities in work
area.

9. Physical and Chemical Properties

Appearance:
Fine crystals, white yellowish-white or pale, fawn-colored.
Odor: Odorless.
Solubility:1.1g/100ml water @ 20C (68F) (anhydrous).
Density: 1.7 (anhydrous)
pH: No information found.
% Volatiles by volume @ 21C (70F): 1
Boiling Point: Not applicable.
Melting Point: 250C (482F)
Vapor Density (Air=1): No information found.

Vapor Pressure (mm Hg): No information found.

Evaporation Rate (BuAc=1): No information found.

10. Stability and Reactivity

Stability: Stable under ordinary conditions of use and storage.
Hazardous Decomposition Products: Carbon dioxide and carbon monoxide may form when
heated to decomposition.
Hazardous Polymerization: Will not occur.
Incompatibilities: Ferric salts, ammonia, strong oxidizing agents, alkalis, nitrous ether, lead
acetate, silver salts, chlorates, permanganate..
Conditions to Avoid: No information found.

11. Toxicological Information

For Anhydrous form: Oral rat LD50: 5g/kg. Investigated as a mutagen, reproductive effector.
--------\CancerLists\-------NTP Carcinogen
Ingredient
Gallic Acid (149-91-7)

Known
No

Anticipated
No

IARC Category
None

12. Ecological Information

Environmental Fate: No information found.
Environmental Toxicity: Harmful to aquatic life in very low concentrations.

13. Disposal Considerations

Whatever cannot be saved for recovery or recycling should be managed in an appropriate and
approved waste disposal facility. Processing, use or contamination of this product may
change the waste management options.
State and local disposal regulations may differ from federal disposal regulations. Dispose of
container and unused contents in accordance with federal, state and local
requirements.

14. Transport Information

Not regulated.

15. Other Information

NFPA Ratings: Health: 1 Flammability: 0 Reactivity: 0
Label Hazard Warning:

CAUTION! MAY CAUSE IRRITATION TO SKIN, EYES, AND RESPIRATORY

TRACT.

Label Precautions:

Avoid contact with eyes, skin and clothing.

Wash thoroughly after handling.

Avoid breathing dust.

Keep container closed.

Use only with adequate ventilation.

Label First Aid:

In case of contact, immediately flush eyes or skin with plenty of water for at least 15 minutes.
If irritation develops call a physician. If inhaled, remove to fresh air. Get medical attention for
any breathing difficulty.
Product Use:
Laboratory Reagent.

Revision Information:
MSDS Section(s) changed since last revision of document include: 1, 8, 12.
Disclaimer:
***************************************************************************
********************
ALNICOLSA del Per S.A.C. provides the information contained herein in good faith
but makes no representation as to its comprehensiveness or accuracy. This document is
intended only as a guide to the appropriate precautionary handling of the material by a
properly trained person using this product.
Individuals receiving the information must exercise their independent judgment in
determining its appropriateness for a particular purpose. ALNICOLSA del Per S.A.C.
MAKES NO REPRESENTATIONS OR WARRANTIES, EITHER EXPRESS OR
IMPLIED, INCLUDING WITHOUT LIMITATION ANY WARRANTIES OF
MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE WITH RESPECT
TO THE INFORMATION SET FORTH HEREIN OR THE PRODUCT TO WHICH
THE INFORMATION REFERS. ACCORDINGLY, ALNICOLSA del Per S.A.C.
WILL NOT BE RESPONSIBLE FOR DAMAGES RESULTING FROM USE OF OR
RELIANCE UPON THIS INFORMATION.
***************************************************************************
********************
REFERENCES
Abella A. & Chalas J. (1997). Antioxidant activity of phenolic acids and esters present in red wine on human LowDensity Lipoproteins. Atherosclerosis, 134, 199-206.
Abu-Amsha Caccetta R., Burke V., Mori T.A., Beilin L.J., Puddey I.B.& Croft K.D. (2001). Red wine polyphenols, in the
absence of alcohol, reduce lipid peroxidative stress in smoking subjects. Free Radic Biol Med, 30, 636-642.
Aoki K., Ishiwata S., Sakagami H., Kusama K.& Katayama T. (2001). Modification of apoptosis-inducing activity of gallic
acid by saliva. Anticancer Res, 21, 1879-1883.
Arce L., Rios A.& Volcarcel M. (1998). Determination of Heterocyclic Aromatic Amines in Fried Beefsteak, Meat Extract,
and Fish by Capillary Zone. J.Chromatogr., 827, 113-120.
Aruoma O.I., Murcie A., Butler J.& Halliwell B. (1993). Antioxidant and pro-oxidant properties of herbs. J. Agricul. Food
Chem., 41, 1880-1885.
Bors W. & Michel C. (1999). Antioxidant capacity of flavanols and gallate esters: pulse radiolysis studies. Free Rad. in
Biol. & Med., 27, 1413-1426.
Bykova L.N., Petrov S.I.& Blagodatskava Z.G. (1970). Relative acidity of phenol and its derivatives in a medium of
nonaqueous solvents. Zh. Obshch. Khim., 40, 2295-3000.
Dowd P.F., Duvick J.P.& Rood T. (1997). Comparative toxicity of allelochemicals and their enzymatic oxidation products
to maize fungal pathogens, emphasizing Fusarium graminearum. Nat Toxins, 5, 180-185.
Eftink M.R. (1991). Fluorescence techniques for studying protein structures.[In:] C. H. Suelter. (Eds.) Fluorescence
techniques for studying protein structures (pp. 127-205). New York: John Wiley & Sons.

Heinonen I.M., Lehtonen P.J.& Hopia A.I. (1998). Antioxidant Activity of Berry and Fruit Wines and Liquors. J Agric
Food Chem, 46, 25-31.
Ho C.T., Chen Q., Shi H., Zhang K.Q.& Rosen R.T. (1992). Antioxidative effect of polyphenol extract prepared from
various Chinese teas. Prev Med, 21, 520-525.
Inoue M., Suzuki R., Sakaguchi N., Li Z., Takeda T., Ogihara Y., Jiang B.Y.& Chen Y. (1995). Selective induction of cell
death in cancer cells by gallic acid. Biol Pharm Bull, 18, 1526-1530.
Kahkonen M.P., Hopia A.I., Vuorela H.J., Rauha J.P., Pihlaja K., Kujala T.S.& Heinonen M. (1999). Antioxidant activity of
plant extracts containing phenolic compounds. J Agric Food Chem, 47, 3954-3962.
Kerry N.L. & Abbey M. (1997). Red wine and fractionated phenolic compounds prepared from red wine inhibit low
density lipoprotein oxidation in vitro. Atherosclerosis, 135, 93-102.
Khan N.S., Ahmad A.& Hadi S.M. (2000). Antioxidant, pro-oxidant properties of tannic acid and its binding to DNA.
Chem Biol Interact, 125, 177-189.
Koga T., Moro K., Nakamori K., Yamakoshi J., Hosoyama H., Kataoka S.& Ariga T. (1999). Increase of antioxidative
potential of rat plasma by oral administration of proanthocyanidin-rich extract from grape seeds. J Agric Food Chem,
47, 1892-1897.
Lakowicz J.R. (1983). Principles of fluorescence spectroscopy, Plenum Press: New York and London.
Landrault N., Poucheret P., Ravel P., Gasc F., Cros G.& Teissedre P.L. (2001). Antioxidant capacities and phenolics levels
of French wines from different varieties and vintages. J Agric Food Chem, 49, 3341-3348.
Lee M.W., Lee Y.A., Park H.M., Toh S.H., Lee E.J., Jang H.D.& Kim Y.H. (2000). Antioxidative phenolic compounds from
the roots of Rhodiola sachalinensis A. Bor. Arch Pharm Res, 23, 455-458.
Li A.S., Bandy B., Tsang S.S.& Davison A.J. (2000). DNA-breaking versus DNA-protecting activity of four phenolic
compounds in vitro. Free Radic Res, 33, 551-566.
Masaki H., Atsumi T.& Sakurai H. (1995). Peroxyl radical scavenging activities of hamamelitannin in chemical and
biological systems. Free Radic Res, 22, 419-430.
Metelitza D.I., Eryomin A.N., Sviridov D.O.& Kamyshnikov V.S. (2001). Initiation and inhibition of free radical processes
in H2O2- metmyoglobin (methemoglobin)-2,2'-azino-bis-(3-ethylbenzthiazoline-6- sulfonic acid) systems.
Biochemistry (Mosc), 66, 505-514.
Milic B.L., Djilas S.M.& Canadovic-Brunet J.M. (1998). ESR spin-trapping studies of influence of phenolic compounds on
hydroxyl radicals formation. Food Chem., 61, 443-447.
Pulido R., Bravo L.& Saura-Calixto F. (2000). Antioxidant activity of dietary polyphenols as determined by a modified
ferric reducing/antioxidant power assay. J Agric Food Chem, 48, 3396-3402.
Romsted L.S. & Zanette D. (1988). Micellar pseudophases in acidic environment J.Phys.Chem., 92, 4690.
Sakagami H., Satoh K., Hatano T., Yoshida T.& Okuda T. (1997). Possible role of radical intensity and oxidation
potential for gallic acid-induced apoptosis. Anticancer Res, 17, 377-380.
Satoh K., Ida Y., Sakagami H., Tanaka T.& Fujisawa S. (1998). Effect of antioxidants on radical intensity and cytotoxic
activity of eugenol. Anticancer Res, 18, 1549-1552.
Schmidt K.N., Traenckner E.B., Meier B.& Baeuerle P.A. (1995). Induction of oxidative stress by okadaic acid is
required for activation of transcription factor NF-kappa B. J Biol Chem, 270, 27136-27142.
Schmitke J.L., Stern L.J.& Klibanov A.M. (1997). The crystal structure of subtilisin Carlsberg in anhydrous dioxane and
its comparison with those in water and acetonitrile. Proc Natl Acad Sci U S A, 94, 4250- 4255.
Sroka Z., Rzadkowska-Bodalska H.& Mazol I. (1994). Antioxidative effect of extracts from Erodium cicutarium L. Z
Naturforsch [C], 49, 881-884.

Terasaka H., Tamura A., Takayama F., Kashimata M., Ohtomo K., Machino M., Fujisawa S., Toguchi M., Kanda Y., Kunii
S., Kusama K., Ishino A., Watanabe S., Satoh K., Takano H., Takahama M.& Sakagami H. (2000). Induction of
apoptosis by dopamine in human oral tumor cell lines. Anticancer Res, 20, 243-250.
Womack M.D., Kendall D.A.& MacDonald R.C. (1983). Detergent effects on enzyme activity and solubilization of lipid
bilayer membranes. Biochim Biophys Acta, 733, 210-215.
Zheng W. & Wang S.Y. (2001). Antioxidant Activity and Phenolic Compounds in Selected Herbs. J Agric Food Chem,
49, 5165-5170.

http://taninos.tripod.com/acidogalico.htm

Substance:Gallic acid

Main ChemSpider page

Molecular formula: C7H6O5

Molar mass: 170.120

CAS Registry Number: Not available

Appearance: 3,4,5-Trihydroxybenzoic acid, anhydrous, 99%; 3,4,5Trihydroxybenzoic acid, anhydrous, 99%; white powder

Melting point: 251

Boiling point: 273 to 274

Solubility: Water, 1.19e+004 mg/L (20 deg C)

Safety sheet: Not available

Spectra: ChemSpider (1H NMR, 13C NMR), NMRShiftDB 13C NMR, Massbank MS
(1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11), also check on SDBS. Add Spectra (Help).

From Wikipedia
Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, a type of organic acid, also
known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak
bark, and other plants. The chemical formula is C6H2(OH)3COOH. Gallic acid is found both
free and as part of tannins.
Salts and esters of gallic acid are termed 'gallates'. Despite its name, it does not contain
gallium.
Gallic acid is commonly used in the pharmaceutical industry. It is used as a standard for
determining the phenol content of various analytes by the Folin-Ciocalteau assay; results are
reported in gallic acid equivalents. Gallic acid can also be used as a starting material in the
synthesis of the psychedelic alkaloid mescaline.
Gallic acid seems to have anti-fungal and anti-viral properties. Gallic acid acts as an
antioxidant and helps to protect human cells against oxidative damage. Gallic acid was found
to show cytotoxicity against cancer cells, without harming healthy cells. Gallic acid is used as
a remote astringent in cases of internal haemorrhage. Gallic acid is also used to treat
albuminuria and diabetes. Some ointments to treat psoriasis and external haemorrhoids
contain gallic acid.
Read more... Edit at Wikipedia...

Other names
3,4,5-Trihydroxybenzoic acid (IUPAC Name); 3,4,5-Trihydroxy-benzoic acid; 3,4,5trihydroxybenzoic zcid

References
Please add any relevant references here.
http://www.rsc.org/learn-chemistry/wiki/Substance:Gallic_acid