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C1259

Sigma-Aldrich

Chorismic acid barium salt from Enterobacter aerogenes

≥55%

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):
C10H8BaO6
CAS Number:
55508-12-8
Molecular Weight:
361.49
MDL number:
MFCD00075702
UNSPSC Code:
12352106
PubChem Substance ID:
24892391
NACRES:
NA.25

form

powder

Quality Level

200

concentration

≥55%

shipped in

dry ice

storage temp.

−70°C

SMILES string

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

InChI

1S/C10H10O6.Ba.2H/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

JFTBXNPYKNMOHD-MVYICHOISA-N

Application

Chorismic acid is used as a precursor for a number of important biological compounds synthesized via the shikimate pathway such as the aromatic amino acids tyrosine and phenylalanine, indole, ubiquinone, 2,3-dihydroxybenzoic acid (DHB), and para-aminobenzoate (pABA).
Intermediate in the biosynthesis of aromatic amino acids via the shikimate pathway.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 2 - STOT SE 3

Target Organs

Eyes,Central nervous system, Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Guy Barros Barcellos et al.
Journal of molecular modeling, 15(2), 147-155 (2008-12-02)
Bacillus anthracis has been employed as an agent of bioterrorism, with high mortality, despite anti-microbial treatment, which strongly indicates the need of new drugs to treat anthrax. Shikimate pathway is a seven step biosynthetic route which generates chorismic acid from
O Kerbarh et al.
Biochemical Society transactions, 33(Pt 4), 763-766 (2005-07-27)
The shikimate biosynthetic pathway is utilized in algae, higher plants, bacteria, fungi and apicomplexan parasites; it involves seven enzymatic steps in which phosphoenolpyruvate and erythrose 4-phosphate are converted into chorismate. In Escherichia coli, five chorismate-utilizing enzymes catalyse the synthesis of
B P Nichols et al.
The Journal of biological chemistry, 264(15), 8597-8601 (1989-05-25)
Escherichia coli p-aminobenzoate synthase is composed of two nonidentical subunits encoded by pabA and pabB and has been assumed to be the sole enzyme responsible for p-aminobenzoate biosynthesis from chorismate and glutamine. Plasmids were constructed that overproduce the p-aminobenzoate synthase
Christopher T Walsh et al.
Natural product reports, 29(1), 37-59 (2011-11-09)
The ortho-, meta-, and para- regioisomers of aminobenzoate are building blocks for a wide range of microbial natural products. Both the ortho-isomer (anthranilate) and PABA derive from the central shikimate pathway metabolite chorismate while the meta-isomer is not available by

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