Mycobacidin
Title: Mycobacidin
CAS Registry Number: 539-35-5
CAS Name: 4-Oxo-2-thiazolidinehexanoic acid
Additional Names: e-[2-(4-thiazolidone)]hexanoic acid; 4-thiazolidone-2-caproic acid; 2-(5-carboxypentyl)-4-thiazolidone; cinnamonin; actithiazic acid; acidomycin
Molecular Formula: C9H15NO3S
Molecular Weight: 217.29
Percent Composition: C 49.75%, H 6.96%, N 6.45%, O 22.09%, S 14.76%
Literature References: Antibiotic substance produced by Streptomyces lavendulae, Streptomyces virginiae and several other Streptomyces spp. Isoln: Tejera et al., Antibiot. Chemother. 2, 333 (1952). Production by fermentation: Grundy et al., US 2678929 (1954 to Abbott). Synthesis: McLamore et al., J. Am. Chem. Soc. 75, 105 (1953); Nienburg, Friedrichsen, DE 931651 (1955 to BASF). Toxicity studies: Miyake et al., Pharm. Bull. 1, 84, 89 (1953). Review: Caltrider, Antibiotics vol. I, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 666-668.
 
Derivative Type: l-Form
Properties: Needles from water, ethanol or ethyl acetate, mp 139-140°. [a]D25 -54° (c = 1 in methanol); [a]D25 -60° (c = 1 in ethanol). pK 5.1. Soluble in water, acetone, alcohol, ethylene dichloride, glacial acetic acid. Aq solns are stable over a wide pH range at room temp. Rapidly loses optical activity in dil alkali to give the racemate. Has in vitro activity against Mycobacterium tuberculosis, M. ranae and M. phlei. LD50 in mice (g/kg): 3.5 i.v., 2 s.c. (Miyake).
Melting point: mp 139-140°
pKa: pK 5.1
Optical Rotation: [a]D25 -54° (c = 1 in methanol); [a]D25 -60° (c = 1 in ethanol)
Toxicity data: LD50 in mice (g/kg): 3.5 i.v., 2 s.c. (Miyake)
 
Derivative Type: Methyl ester
Molecular Formula: C10H17NO3S
Molecular Weight: 231.31
Percent Composition: C 51.92%, H 7.41%, N 6.06%, O 20.75%, S 13.86%
Properties: Needles from ether + hexane, mp 53-54°. [a]D25 -50.9° (methanol).
Melting point: mp 53-54°
Optical Rotation: [a]D25 -50.9° (methanol)
 
Derivative Type: d-Form
Properties: Crystals, mp 138-139°. [a]D25 +57° (methanol).
Melting point: mp 138-139°
Optical Rotation: [a]D25 +57° (methanol)
 
Derivative Type: dl-Form
Properties: Crystals from water, mp 123°.
Melting point: mp 123°

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