Oxaceprol
Structural Formula Vector Image
Title: Oxaceprol
CAS Registry Number: 33996-33-7
CAS Name: (4R)-1-Acetyl-4-hydroxy-L-proline
Additional Names: 4-hydroxy-N-acetylproline; 1-acetyl-4-hydroxy-2-pyrrolidinecarboxylic acid
Manufacturers' Codes: CO-61; AHP-200
Trademarks: Jonctum (Hoechst)
Molecular Formula: C7H11NO4
Molecular Weight: 173.17
Percent Composition: C 48.55%, H 6.40%, N 8.09%, O 36.96%
Literature References: Derivative of hydroxyproline having anti-inflammatory activity. Prepn: R. L. M. Synge, Biochem. J. 33, 1924 (1939); J. J. Kolb, G. Toennies, J. Biol. Chem. 144, 193 (1942); O. Leonardo et al., DE 2301358 corresp to US 3860607 (1973, 1975 to Richardson-Merrell). Elucidation of cyclic conformation and cis/trans isomerism about the amide bond: T. Prange et al., Biochem. Biophys. Res. Commun. 61, 104 (1974). Crystal structure: M. Hospital et al., Biopolymers 18, 1141 (1979). In crystals, the acetyl group is in the trans conformation and the ring is puckered. The trans form is more stable than the cis form in solutions: W. A. Thomas, M. K. Williams, J. Chem. Soc. Chem. Commun. 1972, 994. Anti-inflammatory and wound-healing activity in animals: P. Coirre, B. Coirre, GB 1246141 (1971) related to P. Coirre et al., US 3891765 and US 3932638 (1975, 1976 both to Franco Chimie). Clinical studies of use in several rheumatic conditions: P. Grellat, Rhumatologie 27, 223 (1975); in degenerative joint disease, R. Schubotz, L. Hausmann, Therapiewoche 27, 4248 (1977); in treatment of burns, tumors and other wounds (applied locally): Y. Privat, Gaz. Med. Fr. 84, 618 (1977).
Properties: Crystals from acetone, mp 133-134° (Synge); also reported as mp 126-128° (Leonardo). [a]D20 -116.5° (c = 3.2); [a]D18 -119.5° (c = 3.75). Very sol in alcohol. Sol in water, methanol. Insol in ether, chloroform.
Melting point: mp 133-134° (Synge); mp 126-128° (Leonardo)
Optical Rotation: [a]D20 -116.5° (c = 3.2); [a]D18 -119.5° (c = 3.75)
 
Derivative Type: Monohydrate
Molecular Formula: C7H13NO5
Molecular Weight: 191.18
Percent Composition: C 43.98%, H 6.85%, N 7.33%, O 41.84%
Properties: Crystals from moist ethyl acetate or acetone, mp 74-76°.
Melting point: mp 74-76°
 
Derivative Type: Zinc salt
Molecular Formula: C14H20N2O8Zn
Molecular Weight: 409.73
Percent Composition: C 41.04%, H 4.92%, N 6.84%, O 31.24%, Zn 15.96%
Properties: mp 120°.
Melting point: mp 120°
 
Therap-Cat: Anti-inflammatory; vulnerary.
Keywords: Anti-inflammatory (Nonsteroidal); Vulnerary.

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