In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.
Partial list of saturated dicarboxylic acids
Some common or illustrative examples
:{| class="wikitable skin-invert-image"
|+
!C
! n !! Common name !! Systematic IUPAC name !! Structure !! pK<sub>a</sub>1 !! pK<sub>a</sub>2 !! PubChem
|-
|C2
| 0 || Oxalic acid || ethanedioic acid || 60px || 1.27 || 4.27 || 971
|-
|C3
| 1 || Malonic acid || propanedioic acid || 80px || 2.85 || 5.05 || 867
|-
|C4
| 2 || Succinic acid || butanedioic acid || 100px || 4.21 || 5.41 || 1110
|-
|C5
| 3 || Glutaric acid || pentanedioic acid || 120px || 4.34 || 5.41 || 743
|-
|C6
| 4 || Adipic acid || hexanedioic acid || 140px || 4.41 || 5.41 || 196
|-
|C7
| 5 || Pimelic acid || heptanedioic acid || 160px || 4.50 || 5.43 || 385
|-
|C8
| 6 || Suberic acid || octanedioic acid || 180px || 4.526 || 5.498 || 10457
|-
|C8
| 6 || || 1,4-Cyclohexanedicarboxylic acid || 180px || || ||14106
|-
|C9
| 7 || Azelaic acid || nonanedioic acid || 200px || 4.550 || 5.498 || 2266
|-
|C10
| 8 || Sebacic acid || decanedioic acid || 220px || 4.720 || 5.450 || 5192
|-
|C11
| 9 || || undecanedioic acid || 240px || || || 15816
|-
|C12
| 10 || || dodecanedioic acid || 260px
| || || 12736
|-
|C13
| 11 || Brassylic acid || tridecanedioic acid || 280px || || || 10458
|-
|C14
| 12 || Tetradecanedioic acid || Tetradecanedioic acid] || || || ||
|-
|C16
| 14 || Thapsic acid || hexadecanedioic acid || 300px || || || 10459
|-
|C21
| 19 || Japanic acid || heneicosanedioic acid || 200px || || || 9543668
|-
|C22
| 20 || Phellogenic acid || docosanedioic acid || 280px || || || 244872
|-
|C30
| 28 || Equisetolic acid || triacontanedioic acid || 280px || || || 5322010
|}
Unsaturated dicarboxylic acids
:{| class="wikitable skin-invert-image"
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|-
! Type !! Common name !! IUPAC name !! Isomer !! Structural formula !! PubChem
|-
| rowspan="7" | Monounsaturated || Maleic acid || (Z)-Butenedioic acid || cis || 100px || 444266
|-
| Fumaric acid || (E)-Butenedioic acid || trans || 100px || 444972
|-
| rowspan="2" | Glutaconic acid || (Z)-Pent-2-enedioic acid || cis || 100px || 5370328
|-
| (E)-Pent-2-enedioic acid || trans || 100px || 5280498
|-
| || 2-Decenedioic acid || trans || 200px || 6442613
|-
| Traumatic acid || Dodec-2-enedioic acid || trans || 200px || 5283028
|-
| rowspan="4" | Diunsaturated || rowspan=3 | Muconic acid || (2E,4E)-Hexa-2,4-dienedioic acid || trans,trans
| 100px || 5356793
|-
| (2Z,4E)-Hexa-2,4-dienedioic acid || cis,trans || 100px || 280518
|-
| (2Z,4Z)-Hexa-2,4-dienedioic acid || cis,cis || 100px || 5280518
|-
| Glutinic acid<br />(Allene-1,3-dicarboxylic acid) || (RS)-Penta-2,3-dienedioic acid || || HO<sub>2</sub>CCH=C=CHCO<sub>2</sub>H || 5242834
|-
| rowspan="3" | Branched || Citraconic acid || (2Z)-2-Methylbut-2-enedioic acid || cis || 100px|alt=HO<sub>2</sub>CCH=C(CH<sub>3</sub>)CO<sub>2</sub>H || 643798
|-
| Mesaconic acid || (2E)-2-Methyl-2-butenedioic acid || trans || 100px|alt=HO<sub>2</sub>CCH=C(CH<sub>3</sub>)CO<sub>2</sub>H || 638129
|-
| Itaconic acid || 2-Methylidenebutanedioic acid || – || 100px || 811
|-
| rowspan="7" | Acetylenic ||Acetylenedicarboxylic acid || But-2-ynedioic acid || not applicable || 100px || 371
|-
|}
Substituted dicarboxylic acids
:{| class="wikitable skin-invert-image"
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|-
! Common name !! IUPAC name !! Structural formula !! PubChem
|-
| Tartronic acid || 2-Hydroxypropanedioic acid || 100px || 45
|-
| Mesoxalic acid || Oxopropanedioic acid || 100px || 10132
|-
| Malic acid || Hydroxybutanedioic acid || 100px || 525
|-
| Tartaric acid || 2,3-Dihydroxybutanedioic acid || 120px || 875
|-
| Oxaloacetic acid || Oxobutanedioic acid || 100px || 970
|-
| Aspartic acid || 2-Aminobutanedioic acid || 100px || 5960
|-
| dioxosuccinic acid || dioxobutanedioic acid || 100px || 82062
|-
| α-hydroxyGlutaric acid || 2-hydroxypentanedioic acid || 120px || 43
|-
| Arabinaric acid || 2,3,4-Trihydroxypentanedioic acid || || 109475
|-
| Acetonedicarboxylic acid || 3-Oxopentanedioic acid || 100px || 68328
|-
| α-Ketoglutaric acid || 2-Oxopentanedioic acid || 120px || 51
|-
| Glutamic acid || 2-Aminopentanedioic acid || 120px || 611
|-
| Diaminopimelic acid || (2R,6S)-2,6-Diaminoheptanedioic acid || 150px || 865
|-
| Saccharic acid || (2S,3S,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid || 150px || 33037
|}
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Simple forms of dicarboxylic acids
Hidden: Dubious relevance and un-traceable references -->
<!-- It has been proposed that dicarboxylic acids are alternate lipid substrates in parenteral nutrition. --><!-- Can't locate this reference. PG They are water soluble, undergo b-oxidation, do not induce ketogenesis but rather promote gluconeogenesis. They could represent an immediately available form of energy. Thus, inorganic salts of sebacic and the monocarboxylic acid lauric (C12) acids were firstly proposed, but now, triglycerides containing these fatty acids are under investigation. and inhibited the development of advanced cardiovascular disease. -->
Aromatic dicarboxylic acids
:{| class="wikitable skin-invert-image"
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! Common names !! IUPAC name !! Structure || PubChem
|-
| Phthalic acid<br />o-phthalic acid || Benzene-1,2-dicarboxylic acid || 80px || 1017
|-
| Isophthalic acid<br />m-phthalic acid || Benzene-1,3-dicarboxylic acid || 120px || 8496
|-
| Terephthalic acid<br />p-phthalic acid || Benzene-1,4-dicarboxylic acid || 120px || 7489
|-
| Diphenic acid<br />Biphenyl-2,2′-dicarboxylic acid || 2-(2-Carboxyphenyl)benzoic acid || 110px || 10210
|-
| 2,6-Naphthalenedicarboxylic acid || 2,6-Naphthalenedicarboxylic acid || 150px || 14357
|}
Terephthalic acid is a commodity chemical used in the manufacture of the polyester known by brand names such as PET, Terylene, Dacron and Lavsan.
See also
- Branched-chain dicarboxylic acids
- Tricarboxylic acid
References
External links
- Lipidomics gateway Structure Database Dicarboxylic acids