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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
form:
powder
assay:
≥80%

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

Related Categories

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

signalword

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

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

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000363710
0000363710
0000350679
0000329522
0000222638

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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)
Alexandra Manos-Turvey et al.
ChemMedChem, 5(7), 1067-1079 (2010-06-01)
Mycobacterium tuberculosis salicylate synthase (MbtI), a member of the chorismate-utilizing enzyme family, catalyses the first committed step in the biosynthesis of the siderophore mycobactin T. This complex secondary metabolite is essential for both virulence and survival of M. tuberculosis, the
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)
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
Rita V M Rio et al.
mBio, 3(1), doi:10-doi:10 (2012-02-16)
Ancient endosymbionts have been associated with extreme genome structural stability with little differentiation in gene inventory between sister species. Tsetse flies (Diptera: Glossinidae) harbor an obligate endosymbiont, Wigglesworthia, which has coevolved with the Glossina radiation. We report on the ~720-kb
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