Pantothenic Acid
Title: Pantothenic Acid
CAS Registry Number: 79-83-4
CAS Name: N-[(2R)-2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl]-b-alanine
Additional Names: D(+)-N-(2,4-dihydroxy-3,3-dimethylbutyryl)-b-alanine; chick antidermatitis factor; vitamin B5
Molecular Formula: C9H17NO5
Molecular Weight: 219.23
Percent Composition: C 49.31%, H 7.82%, N 6.39%, O 36.49%
Literature References: A member of the B complex vitamins; essential vitamin for the biosynthesis of coenzyme A in mammalian cells. Occurs ubiquitously in all animal and plant tissue. The richest common source is liver, but jelly of the queen bee contains 6 times as much as liver. Rice bran and molasses are other good sources. Isoln from liver: R. J. Williams et al., J. Am. Chem. Soc. 60, 2719 (1938). Synthesis: E. T. Stiller et al., ibid. 62, 1785 (1940); Reichstein, Grüssner, Helv. Chim. Acta 23, 650 (1940); Grüssner et al., ibid. 1276. Absolute configuration: Hill, Chan, Biochem. Biophys. Res. Commun. 38, 181 (1970). Only the natural, dextrorotatory form has vitamin activity. Review of chemistry, biochemistry and pharmacology: W. Friedrich, Vitamins (de Gruyter, Berlin, 1988) pp 809-835; of metabolism: A. G. Tahiliani, C. J. Beinlich, Vitam. Horm. 46, 165-228 (1991).
Properties: Unstable, viscous oil. Extremely hygroscopic. Easily destroyed by acids, bases, heat. [a]D25 +37.5°. Freely sol in water, ethyl acetate, dioxane, glacial acetic acid; moderately sol in ether, amyl alcohol. Practically insol in benzene, chloroform.
Optical Rotation: [a]D25 +37.5°
 
Derivative Type: Sodium salt
CAS Registry Number: 867-81-2
Molecular Formula: C9H16NNaO5
Molecular Weight: 241.22
Percent Composition: C 44.81%, H 6.69%, N 5.81%, Na 9.53%, O 33.16%
Properties: Very hygroscopic crystals. [a]D25 +27.1° (c = 2). Can be stored in sealed ampuls only.
Optical Rotation: [a]D25 +27.1° (c = 2)
 
Derivative Type: Calcium salt
CAS Registry Number: 137-08-6
Trademarks: Calpanate (Consumers Vitamin); Pantholin (Lilly)
Molecular Formula: C18H32CaN2O10
Molecular Weight: 476.53
Percent Composition: C 45.37%, H 6.77%, Ca 8.41%, N 5.88%, O 33.57%
Literature References: Prepn: Wehrmeister, US 2780645 (1957 to Commercial Solvents); Kagan, US 2845456 (1958 to Upjohn).
Properties: Minute needles from CH3OH. Sweetish taste with slightly bitter aftertaste. Dec 195-196°. Moderately hygroscopic. [a]D20 +28.2° (c = 5). One gram dissolves in 2.8 ml H2O. Sol in glycerol; slightly sol in alcohol, acetone. pH of 5% aq soln: 7.2-8.0; pH in CO2-free water: 8.7.
Optical Rotation: [a]D20 +28.2° (c = 5)
 
Therap-Cat: Vitamin.
Therap-Cat-Vet: Nutritional factor: dietary essential except in horses, ruminants.
Keywords: Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B5.

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