gamma-Oryzanol

Title: g-Oryzanol
CAS Registry Number: 11042-64-1
Additional Names: OZ; g-OZ; g-orizanol
Trademarks: Caclate (Hokuriku); Gammajust 50 (Horita); Gamma-OZ (Kanebo); Gammariza (Toyo); Gammatsul (Nippon Chemiphar); Guntrin (Zensei); Hi-Z (Otsuka); Maspiron (Sawai); Oliver (Sanzen); Oryvita (Ijaku); Oryzaal (Sankei); Thiaminogen (Ohta)
Literature References: Mixture of ferulic acid esters of sterols (campestrol, stigmasterol, b-sitosterol) and triterpene alcohols (cycloartanol, cycloartenol, 24-methylenecycloartanol, cyclobranol) extracted from rice bran, corn and barley oils. Isoln from rice bran oil: R. Kaneko, T. Tsuchiya, J. Chem. Soc. Jpn. Ind. Chem. Sect. 57, 526 (1954); T. Tsuchiya et al., JP 56 7182 (1956 to Agcy Ind. Sci. Technol.), C.A. 52, 15848b (1958); eidem, JP 57 4895 (1957 to Bureau Ind. Technics), C.A. 52, 5758i (1958); from corn oil: T. Tsuchiya, O. Okubo, JP 60 2945 (1960 to Bureau Ind. Technics), C.A. 54, 25609g (1960). Extraction from rice bran, corn and barley oils and purification: T. Yamamoto, DE 1301002 (1969 to Toyo Koatsu), C.A. 71, 128704r (1969). Separation of 3 major components designated oryzanols A, B and C: M. Shimizu et al., Chem. Pharm. Bull. 5, 36 (1957). Structure of A: G. Ohta, M. Shimizu, ibid. 40; of C: eidem, ibid. 6, 325 (1958); G. Ohta, ibid. 8, 5, 9 (1960). Oryzanol B was subsequently found to be a mixture of A and C: M. Shimizu, G. Ohta, ibid. 108. Separation and properties of the seven components of g-oryzanol: T. Endo et al., Yukagaku 17, 344 (1968), C.A. 69, 37319m (1968); eidem, ibid. 18, 63 (1969), C.A. 70, 89042f (1969). General pharmacology: Y. Yamaji et al., Oyo Yakuri 25, 947 (1983), C.A. 99, 151730h (1983). Antioxidant activity in cytochrome model systems: K. Tajima et al., Biochem. Biophys. Res. Commun. 115, 1002 (1983). Effect on lipid metabolism in rats: M. Shinomiya, Tohoku J. Exp. Med. 141, 191 (1983). Antiulcerative effect on gastric lesions in mice: Y. Ichimaru et al., Nippon Yakurigaku Zasshi 84, 537 (1984), C.A. 102, 55922g (1985). Clinical evaluation in chronic gastritis: T. Arai, Kitakanto Igaku 30, 71, 85 (1980); in hyperlipidemia: G. Yoshino et al., Curr. Ther. Res. 45, 543 (1989).
Properties: White or slightly yellowish, tasteless powder with little or no odor. Crystals from acetone, mp 135-137°. uv max (heptane): 216, 231, 291, 315 nm.
Melting point: mp 135-137°
Absorption maximum: uv max (heptane): 216, 231, 291, 315 nm
Derivative Type: Oryzanol A
CAS Registry Number: 21238-33-5
CAS Name: (3b)-9,19-Cyclolanost-24-en-3-ol 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
Additional Names: cycloartenyl ferulate
Molecular Formula: C40H58O4
Molecular Weight: 602.89
Percent Composition: C 79.69%, H 9.70%, O 10.62%
Properties: Prepd as the monohydrate, mp 150-151.5°. [a]D +40° (c = 0.68). uv max (heptane): 231, 290, 315 nm (log e 4.15, 4.24, 4.34).
Melting point: mp 150-151.5°
Optical Rotation: [a]D +40° (c = 0.68)
Absorption maximum: uv max (heptane): 231, 290, 315 nm (log e 4.15, 4.24, 4.34)
Derivative Type: Oryzanol C
CAS Registry Number: 469-36-3
CAS Name: (3b)-24-Methylene-9,19-cyclolanostan-3-ol 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
Additional Names: 24-methylenecycloartanyl ferulate
Molecular Formula: C41H60O4
Molecular Weight: 616.91
Percent Composition: C 79.82%, H 9.80%, O 10.37%
Therap-Cat: Antiulcerative; antilipemic. Also used in treatment of menopausal syndrome.
Keywords: Antilipemic; Antiulcerative.
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