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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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