Chorismic Acid

Chorismic Acid

CAS Registry Number: 617-12-9

CAS Name: (3R-trans)-3-[(1-Carboxyethenyl)oxy]-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid

Additional Names: 3-enolpyruvic ether of trans-3,4-dihydroxycyclohexa-1,5-diene carboxylic acid; a-(5-carboxy-1,2-dihydro-2-hydroxyphenoxy)acrylic acid

Molecular Formula: C10H10O6

Molecular Weight: 226.18

Percent Composition: C 53.10%, H 4.46%, O 42.44%

1H NMR

13 CNMR

Literature References: The first branch point intermediate in the biosynthesis of aromatic amino acids via the shikimate pathway in bacteria, fungi, and higher plants; naturally occurring as the (-)-form. Its existence was predicted, then discovered during development of a mutant of A. aerogenes: M. I. Gibson et al., Nature 195, 1173 (1962); M. I. Gibson, F. Gibson, Biochim. Biophys. Acta 65, 160 (1962). NMR and preliminary structure study: F. Gibson, M. Jackman, Nature 198, 388 (1963). Isoln and metabolism study: M. Gibson, F. Gibson, Biochem. J. 90, 248 (1964). Prepn and characterization of the barium salt: F. Gibson, ibid. 256. Structure, relative and abs config, prepn of the monohydrate: J. M. Edwards, L. M. Jackman, Aust. J. Chem. 18, 1227 (1965). Total synthesis of racemic chorismic acid: D. A. McGowan, G. A. Berchtold, J. Am. Chem. Soc. 104, 1153 (1982); B. Ganem et al., ibid. 6787; improved synthesis: G. A. Berchtold et al., ibid. 105, 6265 (1983); short formal synthesis: G. H. Posner et al., J. Org. Chem. 52, 4836 (1987). Total synthesis of (-)-form: J. L. Pawlak, G. A. Berchtold, ibid. 1765. Potential use in development of herbicides: S. Stinson, Chem. Eng. News 60, 31 (Dec. 6, 1982). Reviews of chorismic acid in biosynthesis of aromatic amino acids: F. Gibson, J. Pittard, Bacteriol. Rev. 32, 465-492 (1968); R. J. Ife et al., J. Chem. Soc. Perkin Trans. 1 1976, 1776-1783; U. Weiss, J. M. Edwards, The Biosynthesis of Organic Compounds (Wiley, New York, 1980) pp 134-143. See also shikimic acid.

Properties: Crystals may be obtained but show marked tendency toward solvent retention, mp 105-108° (dec). [a]D21 -274° (c = 0.16 in water).

Melting point: mp 105-108° (dec)

Optical Rotation: [a]D21 -274° (c = 0.16 in water)

 

Derivative Type: Barium salt trihydrate

Molecular Formula: C10H8BaO6.3H2O

Molecular Weight: 415.54

Percent Composition: C 28.90%, H 3.40%, Ba 33.05%, O 34.65%

Properties: Unstable. uv max (aq soln): 272 nm (e 2700).

Absorption maximum: uv max (aq soln): 272 nm (e 2700)

 

Derivative Type: Monohydrate

Properties: Colorless crystals from ethyl acetate + light petroleum, mp 148-149° (dec); from ether + light petroleum, mp 112° (dec); from ethyl acetate + carbon tetrachloride, mp 115° (dec). [a]255890 -295.5° (c = 0.2 in water). uv max (water): 275 nm (e2630).

Melting point: mp 148-149° (dec); mp 112° (dec); mp 115° (dec)

Optical Rotation: [a]255890 -295.5° (c = 0.2 in water)

Absorption maximum: uv max (water): 275 nm (e 2630)

 

Derivative Type: (±)-Form

Properties: Crystals from ethyl acetate/hexane, mp 139.4-141° (dec).

Melting point: mp 139.4-141° (dec)