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122750

Sigma-Aldrich

trans-Aconitic acid

98%

Synonym(s):

trans-Propene-1,2,3-tricarboxylic acid

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About This Item

Linear Formula:
HO2CCH2C(CO2H)=CHCO2H
CAS Number:
4023-65-8
Molecular Weight:
174.11
Beilstein:
1725830
EC Number:
223-688-6
MDL number:
MFCD00002721
UNSPSC Code:
12352100
PubChem Substance ID:
24847505
NACRES:
NA.22

Assay

98%

form

solid

mp

190 °C (dec.) (lit.)

functional group

carboxylic acid

SMILES string

OC(=O)C\C(=C/C(O)=O)C(O)=O

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)/b3-1+

InChI key

GTZCVFVGUGFEME-HNQUOIGGSA-N

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General description

trans-Aconitic acid is inhibitor of the tricarboxylic acid cycle and was identified in range grasses.

trans-Aconitic acid is an antioxidant used in food and cosmetics preparation and also used as a plasticizer in the polymer industry.

Application

trans-Aconitic acid was used in synthesis of aconitate esters. It may be used for cross-linking polyvinyl alcohol film for preparing composite nanofiltration membranes.

Biochem/physiol Actions

Antimicrobial agent that blocks the transformation of Leishmania donovani amastigotes to prostigotes.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Quantitation of trans-aconitic acid in different stages of the sugar-manufacturing process
Montoya, Guillermo and Londono, et al.
Journal of Agricultural and Food Chemistry, 62, 8314-8831 (2014)
Contribution of trans-aconitic acid to DPPH scavenging ability in different media
Piang-Siong, William and De Caro, et al
Food Chemistry, 214, 447-452 (2017)
R Burau et al.
Science (New York, N.Y.), 150(3697), 766-767 (1965-11-05)
trans-Aconitate ion, an inhibitor of the tricarboxylic acid cycle, was identified in range grasses as trans-aconitic acid, which was isolated in crystalline form. It occurs in surprisingly high concentrations in early-season forage grasses. Dry-weight concentrations of trans-aconitate vary with season
Effect of Cross-Linking Agent Chemistry and Coating Conditions on Physical, Chemical and Separation Properties of PVA-PSf Composite Membranes.
Dlamini DS, et al. et al.
Separation Science and Technology (2013)
Jiayin Pang et al.
Physiologia plantarum, 154(4), 511-525 (2014-10-08)
The aim of this study was to investigate the capacity of three perennial legume species to access sources of varyingly soluble phosphorus (P) and their associated morphological and physiological adaptations. Two Australian native legumes with pasture potential (Cullen australasicum and
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