trans-Aconitic acid

Product Information

Molecular Formula:
C6H6O6
Molecular Weight:
174.11
Description
trans-Aconitic acid (CAS# 4023-65-8) is an intermediate in the isomerization of citrate and isocitrate in the citric acid cycle.
Synonyms
(E)-prop-1-ene-1,2,3-tricarboxylic acid
IUPAC Name
(E)-prop-1-ene-1,2,3-tricarboxylic acid
Canonical SMILES
C(C(=CC(=O)O)C(=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)/b3-1+
InChI Key
GTZCVFVGUGFEME-HNQUOIGGSA-N
Boiling Point
542.6 ℃ at 760 mmHg
Melting Point
190 ℃
Purity
95 %
Density
1.66 g/cm3
Solubility
1 g dissolves in 5.5 ml water at 13 °c, 2 ml at 25 °c; sol in 2 parts 88% alcohol at 12 °c; slightly sol in ether
Appearance
White to off-white crystalline powder
Application
Naturally present in the leaves and tubers of beet root, sugar cane, and other plants; Used as a plasticizer for buna rubber and plastics and to make itaconic acid;; Used as a flavor, antioxidant, and in the preparation of plasticizers and wetting agents.
Storage
Store below +30 ℃.
Refractive Index
1.5860 (estimate)
LogP
-0.44330
Decomposition
When heated to decomp ... Emits acrid smoke
Dissociation Constants
K1 AT 25 °C= 1.58X10-3; K2= 3.5X10-5

Safety Information

Hazards
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Precautionary Statement
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning

Computed Properties

XLogP3
-1
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
4
Exact Mass
174.01643791 g/mol
Monoisotopic Mass
174.01643791 g/mol
Topological Polar Surface Area
112Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
251
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes

Patents

Publication Number Title Priority Date
CN-114058003-A Double metal cyanide catalyst convenient to separate and preparation method thereof 2021-12-06
CN-114085370-A Poly (carbonate-ether) polyol dispersant, high-stability polymer polyol and preparation method thereof 2021-12-06
CN-113999807-A Construction method of recombinant strain and application of recombinant strain in production of itaconic acid 2021-11-02
CN-113793646-A Spectral image unmixing method based on weighted nonnegative matrix decomposition and application thereof 2021-09-29
CN-113817223-A Aconitate polyvinyl chloride plasticizer and preparation method and application thereof 2021-08-30
CN-113447657-A Detection kit for detecting anti-aconitate hydratase-IgG antibody 2021-07-01
CN-113539478-A Metabolic omics-based deep vein thrombosis prediction model establishing method 2021-06-24
CN-113521302-A Multi-arm polyethylene glycol-blocked macroporous silicon peptide nano controlled release system, preparation and application 2021-06-21
CN-113209067-A Application of itaconic acid in preparation of medicine for treating or relieving allergic airway inflammation diseases 2021-05-20
CN-113416300-A Polyester resin and preparation method and application thereof 2021-05-19

Literatures

PMID Publication Date Title Journal
23571415 2013-06-01 Structure-based identification of OATP1B1/3 inhibitors Molecular pharmacology
22768978 2012-08-03 Analysis of urinary metabolic signatures of early hepatocellular carcinoma recurrence after surgical removal using gas chromatography-mass spectrometry Journal of proteome research
22816308 2012-06-01 Cis-aconitic anhydride ethyl ester and phenolic compounds from the seeds of Alisma orientale Natural product communications
21695416 2011-10-01 Metabolomic profiling of the autosomal dominant polycystic kidney disease rat model Clinical and experimental nephrology
20647021 2011-07-10 Biochemical characterisation of aconitase from Corynebacterium glutamicum Journal of biotechnology
21626887 2011-04-01 [Analysis of transporter function and development to clinical application] Seikagaku. The Journal of Japanese Biochemical Society
21673915 2011-01-01 Preliminary study of conformation and drug release mechanism of doxorubicin-conjugated glycol chitosan, via cis-aconityl linkage, by molecular modeling International journal of molecular sciences
20637578 2010-12-15 Antiedematogenic activity and phytochemical composition of preparations from Echinodorus grandiflorus leaves Phytomedicine : international journal of phytotherapy and phytopharmacology
21506489 2010-11-01 Effects of nitrogen treatments and harvesting stages on the aconitic acid, invert sugar and fiber in sweet sorghum cultivars Journal of environmental biology
20461508 2010-08-01 Enhancing itaconic acid production by Aspergillus terreus Applied microbiology and biotechnology
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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