aconitic acid

cis-Aconitic acid (top) and trans-Aconitic acid (bottom)
	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
PubChem	309
ChemSpider	303
UNII	93371T1BXP
MeSH	Aconitate
ChEBI	CHEBI:22211
Jmol-3D images	Image 1
	SMILES O=C(O)CC(=CC(=O)O)C(=O)O ;
	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) ; Key: GTZCVFVGUGFEME-UHFFFAOYSA-N 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 ;
Properties
Molecular formula	C6H6O6
Molar mass	174.11 g mol−1
Appearance	Colorless crystals
Melting point	190 °C (decomp) (trans isomer), 122 °C (cis isomer)
Acidity (pKa)	2.80, 4.46 (trans isomer)
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C or 77 °F, 100 kPa)
	Infobox references

アコニット酸

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/18 22:50:02」(JST)

wiki en

[Wiki en表示]

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[edit]

^ "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: 12
^ Pawolleck, B. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren". Justus Liebig's Annalen der Chemie 178 (2–3): 150–170. doi:10.1002/jlac.18751780203.

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English Journal

Ammonium fluoride as a mobile phase additive in aqueous normal phase chromatography.

Pesek JJ1, Matyska MT2.
Journal of chromatography. A.J Chromatogr A.2015 Jul 3;1401:69-74. doi: 10.1016/j.chroma.2015.05.010. Epub 2015 May 14.
The use of ammonium fluoride as a mobile phase additive in aqueous normal phase chromatography with silica hydride-based stationary phases and mass spectrometry detection is evaluated. Retention times, peak shape, efficiency and peak intensity are compared to the more standard additives formic acid
PMID 26008598

Itaconic Acid: The Surprising Role of an Industrial Compound as a Mammalian Antimicrobial Metabolite.

Cordes T1, Michelucci A, Hiller K.
Annual review of nutrition.Annu Rev Nutr.2015 May 13. [Epub ahead of print]
Itaconic acid is well known as a precursor for polymer synthesis and has been involved in industrial processes for decades. In a recent surprising discovery, itaconic acid was found to play a role as an immune-supportive metabolite in mammalian immune cells, where it is synthesized as an antimicrobi
PMID 25974697

Hydrogen sulfide improves glucose metabolism and prevents hypertrophy in cardiomyocytes.

Liang M1, Jin S1, Wu DD1, Wang MJ1, Zhu YC2.
Nitric oxide : biology and chemistry / official journal of the Nitric Oxide Society.Nitric Oxide.2015 Apr 30;46:114-22. doi: 10.1016/j.niox.2014.12.007. Epub 2014 Dec 15.
INTRODUCTION: Hydrogen sulfide (H2S) has been reported to inhibit myocardial hypertrophy in a cell model of cardiomyocyte hypertrophy. Our previous study also shows an H2S-induced increase in glucose metabolism in insulin-targeting cells. The present study aims to examine the hypothesis that H2S att
PMID 25524832

Japanese Journal

Metabolic Profiling and Predicting the Free Radical Scavenging Activity of Guava (Psidium guajava L.) Leaves According to Harvest Time by ^1H-Nuclear Magnetic Resonance Spectroscopy

KIM So-Hyun,CHO Somi K.,HYUN Sun-Hee,PARK Hae-Eun,KIM Young-Suk,CHOI Hyung-Kyoon
Bioscience, biotechnology, and biochemistry 75(6), 1090-1097, 2011-06-23
… of 3-hydroxybutyric acid, acetic acid, glutamic acid, asparagine, citric acid, malonic acid, trans-aconitic acid, ascorbic acid, maleic acid, cis-aconitic acid, epicatechin, protocatechuic acid, and xanthine than the …
NAID 10029327988

Synthesis and Properties of Polycarboxylate-type Green Surfactants with S- or N-Linkages

Okada Yuu,Banno Taisuke,Toshima Kazunobu,Matsumura Shuichi
Journal of Oleo Science 58(10), 519-528, 2009
… Polycarboxylate-type green surfactants with either sulfide- (S-) or imino- (N-) linkages were prepared in high yields by a single addition reaction of fatty mercaptan or fatty amine with unsaturated polycarboxylic acids such as fumaric, maleic, itaconic and aconitic acids. …
NAID 130000126307

Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release

KAKINOKI Atsufumi,KANEO Yoshiharu,IKEDA Yuka,TANAKA Tetsuro,FUJITA Kahee
Biological & pharmaceutical bulletin 31(1), 103-110, 2008-01-01
… Two isomers of cis-ADOX (cis-configuration) and trans-ADOX (trans-configuration) were generated in the reaction of DOX and cis-aconitic anhydride. …
NAID 110006569983

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