yl group (C(=O)OH).[1] The general formula of a carboxylic acid is R COOH, with R referring to the rest of the (possibly quite large) molecule. Carboxylic acids o ccur widely and include the amino acids (which make up proteins) and acetic acid (which is part of vinegar and occurs in metabolism). Salts and esters of carboxylic acids are called carboxylates. When a carboxyl gr oup is deprotonated, its conjugate base forms a carboxylate anion. Carboxylate i ons are resonance-stabilized, and this increased stability makes carboxylic acid s more acidic than alcohols. Carboxylic acids can be seen as reduced or alkylate d forms of the Lewis acid carbon dioxide; under some circumstances they can be d ecarboxylated to yield carbon dioxide. Contents [hide] 1 Example carboxylic acids and nomenclature 2 Carboxyl radical 3 Physical properties 3.1 Solubility 3.2 Boiling points 3.3 Acidity 3.4 Odor 4 Characterization 5 Occurrence and applications 6 Synthesis 6.1 Industrial routes 6.2 Laboratory methods 6.3 Less-common reactions 7 Reactions 7.1 Specialized reactions 8 See also 9 References 10 External links Example carboxylic acids and nomenclature[edit] Carboxylic acids are commonly identified using their trivial names, and usually have the suffix -ic acid. IUPAC-recommended names also exist; in this system, ca rboxylic acids have an -oic acid suffix.[2] For example, butyric acid (C3H7CO2H) is butanoic acid by IUPAC guidelines. The -oic acid nomenclature detail is base d on the name of the previously-known chemical benzoic acid.[citation needed] Fo r nomenclature of complex molecules containining a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other subs tituents, for example, 3-chloropropanoic acid. Alternately, it can be named as a "carboxy" or "carboxylic acid" substituent on another parent structure, for exa mple, 2-carboxyfuran. The carboxylate anion (R COO-) of a carboxylic acid is usually named with the suff ix -ate, in keeping with the general pattern of -ic acid and -ate for a conjugat e acid and its conjugate base, respectively. For example, the conjugate base of acetic acid is acetate. Straight-chain, saturated carboxylic acids Carbon atoms Common name IUPAC name Chemical formula Common location or use 1 Carbonic acid Carbonic acid OHCOOH Blood and tissues (bicarbonate b uffer system) 1 Formic acid Methanoic acid HCOOH Insect stings 2 Acetic acid Ethanoic acid CH3COOH Vinegar 3 Propionic acid Propanoic acid CH3CH2COOH Preservative for stored grains, body odour 4 Butyric acid Butanoic acid CH3(CH2)2COOH Butter 5 Valeric acid Pentanoic acid CH3(CH2)3COOH Valerian 6 Caproic acid Hexanoic acid CH3(CH2)4COOH Goat fat 7 Enanthic acid Heptanoic acid CH3(CH2)5COOH 8 Caprylic acid Octanoic acid CH3(CH2)6COOH Coconuts and breast milk 9 Pelargonic acid Nonanoic acid CH3(CH2)7COOH Pelargonium 10 Capric acid Decanoic acid CH3(CH2)8COOH Coconut and Palm kernel oil 11 Undecylic acid Undecanoic acid CH3(CH2)9COOH 12 Lauric acid Dodecanoic acid CH3(CH2)10COOH Coconut oil and hand was h soaps 13 Tridecylic acid Tridecanoic acid CH3(CH2)11COOH 14 Myristic acid Tetradecanoic acid CH3(CH2)12COOH Nutmeg 15 Pentadecylic acid Pentadecanoic acid CH3(CH2)13COOH 16 Palmitic acid Hexadecanoic acid CH3(CH2)14COOH Palm oil 17 Margaric acid Heptadecanoic acid CH3(CH2)15COOH 18 Stearic acid Octadecanoic acid CH3(CH2)16COOH Chocolate, waxes , soaps, and oils 19 Nonadecylic acid Nonadecanoic acid CH3(CH2)17COOH Fats, ve getable oils, pheromone 20 Arachidic acid Icosanoic acid CH3(CH2)18COOH Peanut oil Other carboxylic acids Compound class Members unsaturated monocarboxylic acids acrylic acid (2-propenoic acid) CH2=CHCO OH, used in polymer synthesis Fatty acids medium to long-chain saturated and unsaturated monocarboxylic ac ids, with even number of carbons examples docosahexaenoic acid and eicosapentaen oic acid (nutritional supplements) Amino acids the building-blocks of proteins Keto acids acids of biochemical significance that contain a ketone group, e .g. acetoacetic acid and pyruvic acid Aromatic carboxylic acids benzoic acid, the sodium salt of benzoic acid is used as a food preservative, salicylic acid a beta hydroxy type found in many s kin-care products, phenyl alkanoic acids the class of compounds where a phenyl g roup is attached to a carboxylic acid. Dicarboxylic acids containing two carboxyl groups examples adipic acid the monomer used to produce nylon and aldaric acid a family of sugar acids Tricarboxylic acids containing three carboxyl groups example citric acid fou nd in citrus fruits and isocitric acid Alpha hydroxy acids containing a hydroxy group example glyceric acid, glycol ic acid and lactic acid (2-hydroxypropanoic acid) found in sour milk tartaric ac id found in wine Divinylether fatty acids containing a doubly unsaturated carbon chain att ached via an ether bond to a fatty acid, found in some plants Carboxyl radical[edit] The radical COOH (CAS# 2564-86-5) has only a separate fleeting existence.[3] The acid dissociation constant of COOH has been measured using electron paramagnetic resonance spectroscopy.[4] The carboxyl group tends to dimerise to form oxalic a cid.