Aconitic acid

Aconitic acid^[1]
Names
cis-aconitic acid
trans-aconitic acid
IUPAC name Prop-1-ene-1,2,3-tricarboxylic acid
Other names Achilleic acid; Equisetic acid; Citridinic acid; Pyrocitric acid
Identifiers
CAS Number	499-12-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:22211^Y
ChemSpider	[http://www.chemspider.com/Chemical-Structure.303 _TEMPHERE_ = QQQ^YQQQ.html 303 _TEMPHERE_ = QQQ^YQQQ]^N
ECHA InfoCard	100.007.162
MeSH	Aconitate
PubChem CID	309
InChI InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)^Y Key: GTZCVFVGUGFEME-UHFFFAOYSA-N^Y InChI=1/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12) Key: GTZCVFVGUGFEME-UHFFFAOYAL
SMILES O=C(O)CC(=CC(=O)O)C(=O)O
Properties
Chemical formula	C₆H₆O₆
Molar mass	174.11 g·mol⁻¹
Appearance	Colorless crystals
Melting point	190 °C (374 °F; 463 K) (decomposes) (trans isomer), 122 °C (cis isomer)
Acidity (pK_a)	2.80, 4.46 (trans isomer)^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase.

Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid:^[3]

(HO₂CCH₂)₂COH(CO₂H) → HO₂CCH=C(CO₂H)CH₂CO₂H + H₂O

It was first prepared by thermal dehydration.^[4]

References

↑ "Aconitic Acid - Compound Summary (CID 309)". PubChem.
↑ Dawson, R. M. C.; Elliott, D. C.; Elliott, W. H. (1989). Data for Biochemical Research (3rd ed.). Oxford: Clarendon Press. ISBN 9780198552994.
↑ Bruce, W. F. (1937). "Aconitic Acid". Org. Synth. 17: 1. ; Coll. Vol., 2, p. 12
↑ Pawolleck, B. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren" [Substitution products of citric acid and an attempt at the synthesis of the latter]. Justus Liebig's Annalen der Chemie. 178 (2–3): 150–170. doi:10.1002/jlac.18751780203.

Citric acid cycle metabolic pathway
			Oxaloacetate			Malate			Fumarate			Succinate			Succinyl-CoA


Acetyl-CoA				NADH + H⁺	NAD⁺			H₂O		FADH₂	FAD		CoA + ATP(GTP)	P_i + ADP(GDP)
	+	H₂O														NADH + H⁺ + CO₂
		CoA														NAD⁺
					H₂O		H₂O			NAD(P)⁺	NAD(P)H + H⁺			CO₂


			Citrate			cis-Aconitate			Isocitrate			Oxalosuccinate			α-Ketoglutarate

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