17alpha-Hydroxyprogesterone
Structural Formula Vector Image
Title: 17a-Hydroxyprogesterone
CAS Registry Number: 68-96-2
CAS Name: 17-Hydroxypregn-4-ene-3,20-dione
Additional Names: 4-pregnen-17a-ol-3,20-dione
Molecular Formula: C21H30O3
Molecular Weight: 330.46
Percent Composition: C 76.33%, H 9.15%, O 14.52%
Literature References: Isoln from adrenal glands: Pfiffner, North, J. Biol. Chem. 132, 459 (1940); 139, 855 (1941); von Euw, Reichstein, Helv. Chim. Acta 24, 879 (1941). Prepn: Julian et al., US 2648662 (1953 to Glidden); Ringold et al., US 2802839; Stork et al., US 2805203 (both 1957 to Syntex); Chemerda et al., US 2777843; Cutler, Chemerda, US 2786856; US 2786857; Dulaney, McAleer, US 2813060 (all 1957 to Merck & Co.); Cutler et al., J. Org. Chem. 24, 1629 (1959); Pederson, US 3000883 (1961 to Upjohn).
Properties: Rhombic or hexagonal leaflets from acetone or alcohol, mp 222-223° (rapid heating). With slow heating the substance undergoes molecular rearrangement accompanied by partial resolidification and becomes completely molten only at 276°. [a]D17 +105.6° (c = 1.0417 in chloroform).
Melting point: mp 222-223° (rapid heating)
Optical Rotation: [a]D17 +105.6° (c = 1.0417 in chloroform)
 
Derivative Type: Acetate
Additional Names: 17a-Acetoxyprogesterone
Molecular Formula: C23H32O4
Molecular Weight: 372.50
Percent Composition: C 74.16%, H 8.66%, O 17.18%
Properties: Crystals from chloroform + methanol, mp 239-240°. uv max: 240 nm (log e 4.33).
Melting point: mp 239-240°
Absorption maximum: uv max: 240 nm (log e 4.33)
 
Derivative Type: Caproate
CAS Registry Number: 630-56-8
Additional Names: 17a-Hydroxyprogesterone hexanoate
Trademarks: Lentogest (Amsa); Proge (Mochida); Proluton Depot (Schering AG)
Molecular Formula: C27H40O4
Molecular Weight: 428.60
Percent Composition: C 75.66%, H 9.41%, O 14.93%
Literature References: Prepn: Kaspar et al., US 2753360 (1956 to Schering AG). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 4 209-224 (1975).
Properties: Dense needles from isopropyl ether or methanol, mp 119-121°. [a]D20 +61° (c = 1 in chloroform). Soly (mg/ml): sesame oil 25-29; levulinic acid butyl ester 350-400.
Melting point: mp 119-121°
Optical Rotation: [a]D20 +61° (c = 1 in chloroform)
 
Therap-Cat: Progestogen.
Therap-Cat-Vet: Estrus regulator.
Keywords: Progestogen.

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