7011. Pantetheine
Nomenclature
CAS number: 496-65-1
2,4-Dihydroxy-N-[3-[(2-mercaptoethyl)amino]-3-oxopropyl]-3,3-dimethylbutanamide; 2,4-dihydroxy-N-[2-[(2-mercaptoethyl)carbamoyl]ethyl]-3,3-dimethylbutyramide; N-(pantothenyl)-β-aminoethanethiol; α,γ-dihydroxy-β,β-dimethylbutyryl-β-alanyl-β-aminoethanethiol. C11H22N2O4S; mol wt 278.37.
C 47.46%, H 7.97%, N 10.06%, O 22.99%, S 11.52%.
Description and 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. [α]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.Derivative
Silver mercaptide.C11H21AgN2O4S; mol wt 385.23.
C 34.30%, H 5.49%, Ag 28.00%, N 7.27%, O 16.61%, S 8.32%.
Properties
Yellow noncryst solid. [α]D25 +8° (c = 4.27 in 0.9N NaCl). Very sol in water. 11,000 LBF units/mg.Derivative
Mercuric mercaptide.C22H42HgN4O8S2.C3H6O; mol wt 813.39.
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°. [α]D27 +9.6° (c = 4 in water). 15,500 LBF units/mg. uv max: 260-265 nm (ε 1000). Sol in water, methanol.Derivative
S-Benzoylpantetheine.C18H26N2O5S; mol wt 382.47.
C 56.53%, H 6.85%, N 7.32%, O 20.92%, S 8.38%.
Properties
Crystals from ethyl acetate, mp 116°. [α]D27 +31° (ethanol). Sol in water, ethyl acetate, chloroform.Derivative
S-Acetylpantetheine.C13H24N2O5S; mol wt 320.41.
C 48.73%, H 7.55%, N 8.74%, O 24.97%, S 10.01%.