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C1761

Sigma-Aldrich

Chorismic acid from Enterobacter aerogenes

≥80%

Synonym(s):

trans-3-([1-Carboxyethenyl]oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H10O6
CAS Number:
617-12-9
Molecular Weight:
226.18
MDL number:
MFCD00135935
UNSPSC Code:
12352100
PubChem Substance ID:
57653988
NACRES:
NA.22

Quality Level

200

Assay

≥80%

form

powder

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O

InChI

1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1

InChI key

WTFXTQVDAKGDEY-HTQZYQBOSA-N

Application

Chorismic acid is a metabolite generally used in the study of chorismate-prephenate rearrangement and to synthesize chorismate derivatives.
Intermediate in the biosynthesis of aromatic amino acids via the shikimate pathway.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Of two make one: the biosynthesis of phenazines.
Matthias Mentel et al.
Chembiochem : a European journal of chemical biology, 10(14), 2295-2304 (2009-08-07)
Diversity-oriented production of metabolites derived from chorismate and their use in organic synthesis.
Johannes Bongaerts et al.
Angewandte Chemie (International ed. in English), 50(34), 7781-7786 (2011-07-09)
Stabilization of the transition state of the chorismate-prephenate rearrangement: An ab initio study of enzyme and antibody catalysis.
Wiest, Olaf and Houk, KN
Journal of the American Chemical Society, 117(47), 11628-11639 (1995)
Richard J Payne et al.
Organic & biomolecular chemistry, 8(15), 3534-3542 (2010-06-10)
Several 2-amino-4-carboxypyridine, 4- and 5-carboxypyridone-based compounds were prepared and tested against three members of the chorismate-utilising enzyme family, anthranilate synthase, isochorismate synthase and salicylate synthase. Most compounds exhibited low micromolar inhibition of these three enzymes. The most potent inhibitor was
Sergio Martí et al.
Journal of the American Chemical Society, 131(44), 16156-16161 (2009-10-20)
The isochorismate pyruvate lyase (IPL) from Pseudomonas aeruginosa, designated as PchB, catalyzes the transformation of isochorismate into pyruvate and salicylate, but it also catalyzes the rearrangement of chorismate into prephenate, suggesting that both reactions may proceed by a pericyclic mechanism.
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