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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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$238.00
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$473.00
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$700.00
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About This Item

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

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Quality Level

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

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C1259M90003P2384
assay

≥80%

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-

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95%

assay

≥75%

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

storage temp.

−20°C

storage temp.

−70°C

storage temp.

-

storage temp.

−20°C

form

powder

form

powder

form

powder

form

powder

shipped in

dry ice

shipped in

dry ice

shipped in

-

shipped in

dry ice

Application

Chorismic acid is a metabolite generally used in the study of chorismate-prephenate rearrangement and to synthesize chorismate derivatives.[1][2][3]
Intermediate in the biosynthesis of aromatic amino acids via the shikimate pathway.

pictograms

Health hazardExclamation mark

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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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)
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
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)
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.
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

Questions

  1. Which impurities may be present in the product "C1761 Chorismic acid from Enterobacter aerogenes"?

    1 answer
    1. The specific impurities of this material are not identified. However, the minimum purity of this item is 80% with the maximum allowable solvent and water content at 5% and 10%, respectively. A review of recent lots shows a purity range of 96% - 98.5% with accompanying ranges of 0.0% - 4.5% and 1.3% - 5.0% for solvent content and water content, respectively.

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