Aconitic acid

Structural formula
	Structural formulas of cis and trans aconitic acid
General
Surname	Aconitic acid
other names	1,2,3-propentricarboxylic acid
Molecular formula	C 6 H 6 O 6
Brief description	colorless solid
External identifiers / databases
EC number	207-877-0
ECHA InfoCard	100.007.162
PubChem	309
Wikidata	Q288782
properties
Molar mass	174.11 g mol −1
Physical state	firmly
density	0.56 g cm −3 ( trans )
Melting point	194–195 ° C (decomposition) ( trans ); 135 ° C ( cis );
pK s value	pK s 1 : 2.8 ( trans isomer); pK s 2 : 4.46 ( trans isomer);
solubility	very good in water (400 g l −1 at 20 ° C, trans )
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 351
	P: 281
Toxicological data	180 mg kg −1 ( LD 50 , mouse , iv , trans isomer)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Aconitic acid is the common name for 1,2,3-propentricarboxylic acid , an unsaturated organic compound with three carboxylic acid functions . Their salts are called aconites.

Isomers

The aconitic may as cis - or trans - isomer present.

Isomers of aconitic acid
Surname	cis aconitic acid	trans -aconitic acid
other names	( Z ) -aconitic acid	( E ) -aconitic acid
Structural formula
CAS number	585-84-2	4023-65-8
	499-12-7 (unspec.)
EC number	209-564-4	223-688-6
	207-877-0 (unspec.)
ECHA info card	100.008.697	100,021,536
	100.007.162 (unspec.)
PubChem	643757	444212
	309 (unspec.)
Wikidata	Q27104226	Q27104227
	Q288782 (unspec.)

Occurrence

Both isomers of aconitic acid occur in nature.

The cis aconitic acid is an intermediate product in the conversion of citrate to isocitrate by the aconitase in the citric acid cycle and glyoxylate cycle .

It occurs in free form in the blue monkshood flower ( Aconitum napellus ), but also in other plants such as the common yarrow ( Achillea millefolium ) and the Christmas rose .

presentation

Aconitic can be achieved by dehydration of citric acid produced under the influence of concentrated sulfuric acid:

{\ displaystyle \ mathrm {C_ {6} H_ {8} O_ {7} \ {\ xrightarrow [{}] {H_ {2} SO_ {4}}} \ C_ {6} H_ {6} O_ {6} \ + \ H_ {2} O}}

It was first produced in 1875 from citric acid thermally at 170 ° C.

properties

The cis -isomer very easily forms an anhydride , cis -aconitic anhydride with a melting point of 75 ° C.

Individual evidence

↑ Data sheet cis-aconitic acid from AlfaAesar, accessed on May 8, 2010 ( PDF )(JavaScript required) .
↑ Data sheet trans-aconitic acid from AlfaAesar, accessed on May 8, 2010 ( PDF )(JavaScript required) .
↑ ^a ^b data sheet trans-aconitic acid (PDF) from Carl Roth , accessed on May 8, 2010.
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on aconitic acid. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
↑ ^a ^b data sheet cis-Aconitic acid from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).
↑ Bruce, WF: Aconitic acid In: Organic Syntheses . 17, 1937, p. 1, doi : 10.15227 / orgsyn.017.0001 ; Coll. Vol. 2, 1943, p. 12 ( PDF ).
↑ B. Pawolleck: substitution products of citric acid and an attempt for the synthesis of the latter. In: Justus Liebig's Annals of Chemistry. 178, 1875, p. 150, doi : 10.1002 / jlac.18751780203 .
↑ External identifiers or database links for cis-aconitic anhydride : CAS number: 6318-55-4, EC number: 228-663-3, ECHA InfoCard: 100.026.058 , PubChem : 65163 , Wikidata : Q55972704 .

[alfacis-1] Data sheet cis-aconitic acid from AlfaAesar, accessed on May 8, 2010 ( PDF )(JavaScript required) .

[alfatrans-2] Data sheet trans-aconitic acid from AlfaAesar, accessed on May 8, 2010 ( PDF )(JavaScript required) .

[ROTH-3] ta sheet trans-aconitic acid (PDF) from Carl Roth , accessed on May 8, 2010.

[roempp-4] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on aconitic acid. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.

[Sigma-5] ta sheet cis-Aconitic acid from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).

[6] Bruce, WF: Aconitic acid In: Organic Syntheses . 17, 1937, p. 1, doi : 10.15227 / orgsyn.017.0001 ; Coll. Vol. 2, 1943, p. 12 ( PDF ).

[DOI10.1002/jlac.18751780203-7] B. Pawolleck: substitution products of citric acid and an attempt for the synthesis of the latter. In: Justus Liebig's Annals of Chemistry. 178, 1875, p. 150, doi : 10.1002 / jlac.18751780203 .

[8] External identifiers or database links for cis-aconitic anhydride : CAS number: 6318-55-4, EC number: 228-663-3, ECHA InfoCard: 100.026.058 , PubChem : 65163 , Wikidata : Q55972704 .