Title: Amylpenicillin
CAS Registry Number: 4493-18-9
CAS Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(1-oxohexyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: dihydropenicillin F; hexanoylpenicillin; penicillin DF
Molecular Formula: C14H22N2O4S
Molecular Weight: 314.40
Percent Composition: C 53.48%, H 7.05%, N 8.91%, O 20.36%, S 10.20%
Literature References: Antibiotic produced by the mold Aspergillus flavus from a Czapek-Dox medium supplemented with corn steep liquor or by Penicillium chrysogenum Q176 or by P. notatum strains: McKee, MacPhillamy, Proc. Soc. Exp. Biol. Med. 53, 247 (1943); Bush, Goth, J. Pharmacol. Exp. Ther. 78, 164 (1943); McKee et al., J. Bacteriol. 47, 187 (1944); Bush et al., J. Pharmacol. Exp. Ther. 84, 264 (1945); Fried et al., J. Biol. Chem. 163, 341 (1946); see also Wintersteiner under "Flavacidin" in Chemistry of Penicillin (Princeton, 1949). Prepn by hydrogenation of 2-pentenylpenicillin: Catch et al., GB 584852; Cook, Heilbron in Chemistry of Penicillin (Princeton, 1949). Characterization and antibacterial activity: Leigh, Nature 163, 95 (1949).
Derivative Type: Sodium salt
CAS Registry Number: 575-47-3
Additional Names: Sodium n-amylpenicillinate; flavacidin; flavicin
Molecular Formula: C14H21N2NaO4S
Molecular Weight: 336.38
Percent Composition: C 49.99%, H 6.29%, N 8.33%, Na 6.83%, O 19.03%, S 9.53%
Properties: Flat, blunt-ended needles from moist acetone or moist ethyl acetate as the monohydrate. When anhydrous, mp 188° (dec). [a]D23 +319°. Very soluble in water.
Melting point: mp 188° (dec)
Optical Rotation: [a]D23 +319°
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