CAS No 496-65-1 , (2R)-2,4-dihydroxy-3,
3-dimethyl-N-[3-oxo-3-(2-sulfanylethylamino)propyl]butanamide

Title: Pantetheine
CAS Registry Number: 496-65-1
CAS Name: 2,4-Dihydroxy-N-[3-[(2-mercaptoethyl)amino]-3-oxopropyl]-3,3-dimethylbutanamide
Synonyms: 2,4-dihydroxy-N-[2-[(2-mercaptoethyl)carbamoyl]ethyl]-3,3-dimethylbutyramide; N-(pantothenyl)-b-aminoethanethiol; a,g-dihydroxy-b,b-dimethylbutyryl-b-alanyl-b-aminoethanethiol
Molecular Formula: C11H22N2O4S
Molecular Weight: 278.37
Percent Composition: C 47.46%, H 7.97%, N 10.06%, O 22.99%, S 11.52%
Literature References: Growth factor for Lactobacillus bulgaricus: Williams et al., J. Biol. Chem. 177, 933 (1949). Intermediate in the pathway of coenzyme A, q.v., formation in mammalian liver and in some microorganisms. Synthesis: Schwyzer, Helv. Chim. Acta 35, 1903 (1952); Baddiley, Thain, J. Chem. Soc. 1952, 800; King et al., J. Am. Chem. Soc. 75, 1290 (1953); Walton et al., ibid. 76, 1146 (1954); Walton, US 2744119 and US 2835704 (1956, 1958, both to Merck & Co.). Reviews: Snell, Brown, Adv. Enzymol. 14, 49 (1953); Snell, Wittle, Methods Enzymol. 3, 918 (1957).
Properties: Syrup or glass. [a]D20 +12.9° (c = 4.5 in water). Microbiological activity: 20,000 LBF units/mg. An LBF unit is that amount of the growth factor contained in one mg of Basamine-Busch, a standard yeast extract manuf by Anheuser-Busch, Inc.
Optical Rotation: [a]D20 +12.9° (c = 4.5 in water)
 
Derivative Type: Silver mercaptide
Molecular Formula: C11H21AgN2O4S
Molecular Weight: 385.23
Percent Composition: C 34.30%, H 5.49%, Ag 28.00%, N 7.27%, O 16.61%, S 8.32%
Properties: Yellow noncryst solid. [a]D25 +8° (c = 4.27 in 0.9N NaCl). Very sol in water. 11,000 LBF units/mg.
Optical Rotation: [a]D25 +8° (c = 4.27 in 0.9N NaCl)
 
Derivative Type: Mercuric mercaptide
Molecular Formula: C22H42HgN4O8S2.C3H6O
Molecular Weight: 813.39
Percent Composition: C 36.92%, H 5.95%, Hg 24.66%, N 6.89%, O 17.70%, S 7.88%
Properties: Crystals from acetone, mp 96-98°. [a]D27 +9.6° (c = 4 in water). 15,500 LBF units/mg. uv max: 260-265 nm (e 1000). Sol in water, methanol.
Melting point: mp 96-98°
Optical Rotation: [a]D27 +9.6° (c = 4 in water)
Absorption maximum: uv max: 260-265 nm (e 1000)
 
Derivative Type: S-Benzoylpantetheine
Molecular Formula: C18H26N2O5S
Molecular Weight: 382.47
Percent Composition: C 56.53%, H 6.85%, N 7.32%, O 20.92%, S 8.38%
Properties: Crystals from ethyl acetate, mp 116°. [a]D27 +31° (ethanol). Sol in water, ethyl acetate, chloroform.
Melting point: mp 116°
Optical Rotation: [a]D27 +31° (ethanol)
 
Derivative Type: S-Acetylpantetheine
Molecular Formula: C13H24N2O5S
Molecular Weight: 320.41
Percent Composition: C 48.73%, H 7.55%, N 8.74%, O 24.97%, S 10.01%
Properties: Thick syrup. [a]D27 +39° (c = 0.8 in ethanol).
Optical Rotation: [a]D27 +39° (c = 0.8 in ethanol)