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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

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

Exclamation markHealth hazard
GHS07,GHS08

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

Certificates of Analysis (COA)

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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
Kristin T Ziebart et al.
Journal of medicinal chemistry, 53(9), 3718-3729 (2010-04-03)
Chorismate-utilizing enzymes are attractive antimicrobial drug targets due to their absence in humans and their central role in bacterial survival and virulence. The structural and mechanistic homology of a group of these inspired the goal of discovering inhibitors that target
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
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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