Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature, which ensures systematic and consistent naming of chemicals. Numerous organic compounds have other common names, often originating in historical source material thereof. The systematic IUPAC name is not always the preferred IUPAC name, for example, lactic acid is a common, and also the preferred, name for what systematic rules call 2-hydroxypropanoic acid.
This list is ordered by the number of carbon atoms in a carboxylic acid.
Common name | IUPAC name | Structural formula | Notes |
formic acid | methanoic acid | HCO2H | |
carbonic acid | hydroxymethanoic acid | HOCO2H | Despite having an organic-like name, H2CO3 is not considered an organic compound. |
Common name | IUPAC name | Structural formula |
Acetic acid | ethanoic acid | CH3CO2H |
Glycolic acid | hydroxyacetic acid | HOCH2CO2H |
Glyoxylic acid | oxoacetic acid | OHCCO2H |
Oxalic acid | ethanedioic acid | HO2CCO2H |
IUPAC name | Common name | Structural formula |
Propionic acid | propanoic acid ethanecarboxylic acid | CH3CH2CO2H |
Acrylic acid | propenoic acid acroleic acid ethylenecarboxylic acid vinylformic acid | CH2=CHCO2H |
Propiolic acid | propynoic acid propargylic acid acetylene carboxylic acid | CH≡CCO2H |
Lactic acid | 2-hydroxypropanoic acid milk acid | CH3CHOHCO2H |
3-Hydroxypropionic acid | 3-hydroxypropanoic acid hydracrylic acid | CH2OHCH2CO2H |
Glyceric acid | 2,3-dihydroxypropanoic acid | CH2OHCHOHCO2H |
Pyruvic acid | 2-oxopropanoic acid α-ketopropionic acid acetylformic acid pyroracemic acid | CH3COCO2H |
3-oxopropanoic acid | malonic semialdehyde 3-oxopropionic acid | OHCCH2CO2H |
2,3-dioxopropanoic acid | mesoxalic semialdehyde dioxopropionic acid | OHCCOCO2H |
Malonic acid | propanedioic acid methanedicarboxylic acid | HO2CCH2CO2H |
Tartronic acid | 2--hydroxypropanedioic acid hydroxymalonic acid | HO2CCHOHCO2H |
2,2-dihydroxypropanedioic acid | dihydroxymalonic acid mesoxalic acid monohydrate | HO2CC(OH)2CO2H |
Mesoxalic acid | oxopropanedioic acid ketomalonic acid oxomalonic acid | HO2CCOCO2H |
Glycidic acid | 2-oxiranecarboxylic acid oxirane-2-carboxylic acid | CH2OCHCO2H |
IUPAC name | Common name | Structural formula |
butanoic acid | butyric acid propanecarboxylic acid | CH3(CH2)2COOH |
2-methylpropanoic acid | isobutyric acid isobutanoic acid | (CH3)2CHCOOH |
(E)-but-2-enoic acid | crotonic acid trans-butenoic acid 3-methylacrylic acid β-methacrylic acid (E)-2-butenoic acid | CH3CH=CHCOOH |
(Z)-but-2-enoic acid | isocrotonic acid cis-crotonic acid cis-butenoic acid (Z)-2-butenoic acid | CH3CH=CHCOOH |
2-methylpropenoic acid | methacrylic acid α-methacrylic acid 2-methylacrylic acid isobutenoic acid | CH2=C(CH3)COOH |
but-3-enoic acid | vinylacetic acid allylic acid 3-butenoic acid β-butenoic acid | CH2=CHCH2COOH |
but-2-ynoic acid | tetrolic acid 2-butynoic acid | CH3C≡CCOOH |
2-hydroxybutanoic acid | 2-hydroxybutyric acid α-hydroxybutyrate | CH3CH2CHOHCOOH |
3-hydroxybutanoic acid | β-hydroxybutyric acid 3-hydroxybutyric acid | CH3CHOHCH2COOH |
4-hydroxybutanoic acid | γ-hydroxybutyric acid GHB 4-hydroxybutyric acid | HOCH2(CH2)2COOH |
2-oxobutanoic acid | α-ketobutyric acid | CH3CH2COCOOH |
3-oxobutanoic acid | acetoacetic acid diacetic acid | CH3COCH2COOH |
4-oxobutanoic acid | succinic semialdehyde | OHC(CH2)2COOH |
butanedioic acid | succinic acid | HOOC(CH2)2COOH |
2-methylpropanedioic acid | methylmalonic acid | HOOCCH(CH3)COOH |
(E)-butenedioic acid | fumaric acid trans-1,2-ethylenedicarboxylic acid trans-butenedioic acid allomaleic acid boletic acid donitic acid lichenic acid | HOOCCH=CHCOOH |
(Z)-butenedioic acid | maleic acid cis-butenedioic acid malenic acid maleinic acid toxilic acid | HOOCCH=CHCOOH |
butynedioic acid | acetylenedicarboxylic acid 2-butynedioic acid | HOOCC≡CCOOH |
hydroxybutanedioic acid | malic acid hydroxysuccinic acid 2-hydroxybutanedioic acid | HOOCCH2CHOHCOOH |
2,3-dihydroxybutanedioic acid | tartaric acid 2,3-dihydroxysuccinic acid racemic acid threaric acid uvic acid paratartaric acid | HOOC(CHOH)2COOH |
oxobutanedioic acid | oxaloacetic acid oxalacetic acid oxosuccinic acid ketosuccinic acid | HOOCCH2COCOOH |
dioxobutanedioic acid | dioxosuccinic acid | HOOC(CO)2COOH |
IUPAC name | Common name | Structural formula |
pentanoic acid | valeric acid valerianic acid butane-1-carboxylic acid | CH3(CH2)3COOH |
3-methylbutanoic acid | isovaleric acid isopentanoic acid delphinic acid β-methylbutiric acid 3-methylbutiric acid | (CH3)2CHCH2COOH |
2-methylbutanoic acid | 2-methylbutiric acid | CH3CH2CH(CH3)COOH |
2,2-dimethylpropanoic acid | pivalic acid trimethylacetic acid neopentanoic acid | (CH3)3CCOOH |
3-hydroxypentanoic acid | β-hydroxyvaleric acid 3-hydroxyvaleric acid β-hydroxypentanoate | CH3CH2CHOHCH2COOH |
4-hydroxypentanoic acid | γ-hydroxyvaleric acid GHV 4-methyl-GHB | CH3CHOH(CH2)2COOH |
3-hydroxy-3-methylbutanoic acid | β-hydroxy β-methylbutyric acid HMB β-hydroxyisovaleric acid 3-hydroxyisovaleric acid | (CH3)2COHCH2COOH |
pentanedioic acid | glutaric acid propane-1,3-dicarboxylic acid n-pyrotartaric acid | HOOC(CH2)3COOH |
2-oxopentanedioic acid | α-ketoglutaric acid 2-ketoglutaric acid 2-oxoglutaric acid oxoglutaric acid | HOOC(CH2)2COCOOH |
3-oxopentanedioic acid | acetonedicarboxylic acid 3-oxoglutaric acid β-ketoglutaric acid 3-ketoglutaric acid | HOOCCH2COCH2COOH |
furan-2-carboxylic acid | 2-furoic acid α-furoic acid pyromucic acid 2-carboxyfuran α-furancarboxylic acid | furyl-COOH |
tetrahydrofuran-2-carboxylic acid | tetrahydro-2-furoic acid tetrahydrofuroic acid tetrahydrofuran-2-carboxylic acid | tetrahydrofuryl-COOH |
IUPAC name | Common name | Structural formula |
hexanoic acid | caproic acid n-caproic acid | CH3(CH2)4COOH |
hexanedioic acid | adipic acid hexane-1,6-dioic acid | HOOC(CH2)4COOH |
2,3-dimethylbutanoic acid | CH3(CHCH3)2COOH | |
3,3-dimethylbutanoic acid | CH3C(CH3)2CH2COOH | |
2-hydroxypropane-1,2,3-tricarboxylic acid | citric acid 3-carboxy-3-hydroxypentanedioic acid 2-hydroxy-1,2,3-propanetricarboxylic acid | HOC(COOH)((CH2)COOH)2 |
prop-1-ene-1,2,3-tricarboxylic acid | aconitic acid achilleic acid equisetic acid citridinic acid pyrocitric acid | HOOCCH=C(COOH)CH2COOH |
1-hydroxypropane-1,2,3-tricarboxylic acid | isocitric acid | HOOCCHOHCH(COOH)CH2COOH |
(2E,4E)-hexa-2,4-dienoic acid | sorbic acid | CH3(CH=CH)2COOH |
IUPAC name | Common name | Structural formula |
heptanoic acid | enanthic acid oenanthic acid n-Heptylic acid n-Heptoic acid | CH3(CH2)5COOH |
heptanedioic acid | pimelic acid | HOOC(CH2)5COOH |
cyclohexanecarboxylic acid | C 6H 11COOH | |
benzenecarboxylic acid | benzoic acid carboxybenzene dracylic acid | C 6H 5COOH |
2-hydroxybenzoic acid | salicylic acid | HOC 6H 4COOH |
2,2-dimethylpentanoic acid | CH3(CH2)2C(CH3)2COOH | |
2,3-dimethylpentanoic acid | C2H5(CHCH3)2COOH | |
2,4-dimethylpentanoic acid | CH3(CHCH3)CH2(CHCH3)COOH | |
3,3-dimethylpentanoic acid | C2H5C(CH3)2CH2COOH | |
2-ethylpentanoic acid | C3H7CH(C2H5)COOH | |
3-ethylpentanoic acid | C2H5CH(C2H5)CH2COOH | |
2-methylhexanoic acid | C4H9CH(CH3)COOH | |
3-methylhexanoic acid | C3H7CH(CH3)CH2COOH | |
2,2,3-trimethylbutanoic acid | CH3CH(CH3)C(CH3)2COOH | |
2-ethyl-2-methylbutanoic acid | C2H5C(C2H5)(CH3)COOH | |
2-ethyl-3- methylbutanoic acid | CH3CH(CH3)CH(C2H5)COOH |
IUPAC name | Common name | Structural formula |
octanoic acid | caprylic acid | CH3(CH2)6COOH |
benzene-1,2-dicarboxylic acid | phthalic acid | C6H4(COOH)2 |
benzene-1,3-dicarboxylic acid | isophthalic acid | C6H4(COOH)2 |
benzene-1,4-dicarboxylic acid | terephthalic acid | C6H4(COOH)2 |
2-methylheptanoic acid | C5H11CH(CH3)COOH | |
3-methylheptanoic acid | C4H9CH(CH3)CH2COOH | |
4-methylheptanoic acid | C3H7CH(CH3)C2H4COOH | |
5-methylheptanoic acid | C2H5CH(CH3)C3H6COOH | |
6-methylheptanoic acid | (CH3)2CHC4H8COOH | |
2,2-dimethylhexanoic acid | C4H9C(CH3)2COOH | |
2,3-dimethylhexanoic acid | C3H7[CH(CH3)]2COOH | |
2,4-dimethylhexanoic acid | C2H5CH(CH3)CH2CH(CH3)COOH | |
2,5-dimethylhexanoic acid | CH3CH(CH3)C2H4(CH3)COOH | |
3,3-dimethylhexanoic acid | C3H7C(CH3)2CH2COOH | |
3,4-dimethylhexanoic acid | C2H5[CH(CH3)]2CH2COOH | |
3,5-dimethylhexanoic acid | (CH3)2CHCH2CH(CH3)CH2COOH | |
4,4-dimethylhexanoic acid | C2H5C(CH3)2C2H4COOH | |
4,5-dimethylhexanoic acid | CH3[CH(CH)3]2C2H4COOH | |
5,5-dimethylhexanoic acid | (CH3)3CC3H6COOH | |
2-ethanehexanoic acid | C4H9CH(C2H5)COOH | |
3-ethanehexanoic acid | C3H7CH(C2H5)CH2COOH | |
4-ethanehexanoic acid | C2H5CH(C2H5)C2H4COOH | |
5-ethanehexanoic acid | CH3CH(C2H5)C3H6COOH | |
2-octenoic acid | C5H11CH=CHCOOH | |
3-octenoic acid | C4H9CH=CHCH2COOH | |
4-octenoic acid | C3H7CH=CHC2H4COOH | |
5-octenoic acid | C2H5CH=CHC3H6COOH | |
6-octenoic acid | CH3CH=CHC4H8COOH | |
7-octenoic acid | CH2=CHC5H10COOH |
2-6 dimethyl octen dioic acid
IUPAC name | Common name | Structural formula |
nonanoic acid | pelargonic acid 1-octanecarboxylic acid | CH3(CH2)7COOH |
benzene-1,3,5-tricarboxylic acid | trimesic acid | C 6H 3(COOH) 3 |
(E)-3-phenylprop-2-enoic acid | cinnamic acid trans-cinnamic acid phenylacrylic acid cinnamylic acid 3-phenylacrylic acid (E)-cinnamic acid benzenepropenoic acid isocinnamic acid | C 6H 5CH=CHCOOH |
IUPAC name | Common name | Structural formula |
decanoic acid | capric acid | CH3(CH2)8COOH |
decanedioic acid | sebacic acid 1,8-octanedicarboxylic acid | HOOC(CH2)8COOH |
IUPAC name | Common name | Structural formula |
undecanoic acid | hendecanoic acid | CH3(CH2)9COOH |
IUPAC name | Common name | Structural formula |
dodecanoic acid | lauric acid dodecylic acid dodecoic acid laurostearic acid fulvic acid 1-undecanecarboxylic acid duodecylic acid | CH3(CH2)10COOH |
benzene-1,2,3,4,5,6-hexacarboxylic acid | mellitic acid graphitic acid benzenehexacarboxylic acid | C 6(COOH) 6 |
IUPAC name | Common name | Structural formula |
tridecanoic acid | tridecylic acid | CH3(CH2)11COOH |
IUPAC name | Common name | Structural formula |
tetradecanoic acid | myristic acid | CH3(CH2)12COOH |
IUPAC name | Common name | Structural formula |
pentadecanoic acid | pentadecylic acid | CH3(CH2)13COOH |
IUPAC name | Common name | Structural formula |
hexadecanoic acid | palmitic acid | CH3(CH2)14COOH |
IUPAC name | Common name | Structural formula |
heptadecanoic acid | margaric acid heptadecylic acid | CH3(CH2)15COOH |
IUPAC name | Common name | Structural formula |
octadecanoic acid | stearic acid | CH3(CH2)16COOH |
(9Z)-octadec-9-enoic acid | oleic acid (9Z)-octadecenoic acid (Z)-octadec-9-enoic acid cis-9-octadecenoic acid cis-Δ9-octadecenoic acid | CH3(CH2)7CH=CH(CH2)7COOH |
(9Z,12Z)-octadeca-9,12-dienoic acid | linoleic acid | CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH |
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid | ALA α-linolenic acid cis, cis,cis-9,12,15-octadecatrienoic acid (Z,Z,Z)-9,12,15-octadecatrienoic acid | CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH |
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid | GLA γ-linolenic acid gamolenic acid | CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4COOH |
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid | SDA stearidonic acid moroctic acid | CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)5COOH |
IUPAC name | Common name | Structural formula |
nonadecanoic acid | nonadecylic acid | CH3(CH2)17COOH |
IUPAC name | Common name | Structural formula |
icosanoic acid | arachidic acid arachic acid | CH3(CH2)18COOH |
(5Z,8Z,11Z)-eicosa-5,8,11-trienoic acid | Mead's acid | CH3(CH2)7CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH |
(5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoic acid | AA ARA arachidonic acid | CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH |
(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14-pentaenoic acid | EPA | CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH |
IUPAC name | Common name | Structural formula |
heneicosanoic acid | CH3(CH2)19COOH |
IUPAC name | Common name | Structural formula |
docosanoic acid | behenic acid | CH3(CH2)20COOH |
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid | DHA cervonic acid | CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)2COOH |
IUPAC name | Common name | Structural formula |
tricosanoic acid | tricosylic acid | CH3(CH2)21COOH |
IUPAC name | Common name | Structural formula |
tetracosanoic acid | lignoceric acid | CH3(CH2)22COOH |
IUPAC name | Common name | Structural formula |
pentacosanoic acid | pentacosylic acid | CH3(CH2)23COOH |
IUPAC name | Common name | Structural formula |
hexacosanoic acid | cerotic acid | CH3(CH2)24COOH |
A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
An ester is a chemical compound derived from an oxoacid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.
In chemistry, a ketone is a functional group with the structure R2C=O, where R can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond). The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.
In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres.
In organic chemistry, acetyl is a moiety, the acyl with chemical formula CH3CO. It is sometimes represented by the symbol Ac (not to be confused with the element actinium).
An acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an alkyl group (R-C=O). In organic chemistry, the acyl group is usually derived from a carboxylic acid, in which case it has the formula RCO–, where R represents an alkyl group that is linked to the carbon atom of the group by a single bond. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond.
An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2H
3O−
2. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3CO−
2, or CH
3COO−
.
In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.
An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride. Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").
In organic chemistry, a carbodiimide is a functional group with the formula RN=C=NR. They are exclusively synthetic. A well known carbodiimide is dicyclohexylcarbodiimide, which is used in peptide synthesis. Dialkylcarbodiimides are stable. Some diaryl derivatives tend to convert to dimers and polymers upon standing at room temperature, though this mostly occurs with low melting point carbodiimides that are liquids at room temperature. Solid diaryl carbodiimides are more stable, but can slowly undergo hydrolysis in the presence of water over time.
Propiolic acid is the organic compound with the formula HC2CO2H. It is the simplest acetylenic carboxylic acid. It is a colourless liquid that crystallises to give silky crystals. Near its boiling point, it decomposes.
Cyclohexanecarboxylic acid is the organic compound with the formula C6H11CO2H. It is the carboxylic acid of cyclohexane. It is a colorless oil that crystallizes near room temperature.
Acetoxy group, abbreviated AcO or OAc, preferred IUPAC name acetyloxy, is a chemical functional group of the structure CH3-C(=O)-O-. It differs from the acetyl group CH3-C(=O)- by the presence of one additional oxygen atom. The name acetoxy is the short form of acetyl-oxy.
The suffix -oate is the IUPAC nomenclature used in organic chemistry to form names of compounds formed from carboxylic acids. They are of two types:
Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups, and therefore is a dithiol. It is optically active, but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.
Diphenylphosphoryl azide (DPPA) is an organic compound. It is widely used as a reagent in the synthesis of other organic compounds.
In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choosing between multiple possibilities in situations where it is important to decide on a unique name. It is intended for use in legal and regulatory situations.
Chloroformic acid is an unstable chemical compound with the formula ClCO2H. It is the single acyl-halide derivative of carbonic acid (phosgene is the double acyl-halide derivative). Chloroformic acid is also structurally related to formic acid, which has a hydrogen instead of the chlorine. Despite the similar name, it is very different from chloroform.