γ-Oryzanol

(Redirected from Gamma oryzanol)

γ-Oryzanol
Names
Other names gamma-Oryzanol; gamma-Orizanol
Identifiers
CAS Number	11042-64-1 Oryzanol A: 21238-33-5 Oryzanol C: 469-36-3 Campesteryl ferulate: 20972-07-0
3D model (JSmol)	Oryzanol A: Interactive image Oryzanol C: Interactive image Campesteryl ferulate: Interactive image
ChemSpider	Oryzanol A: 4445360 Oryzanol C: 8095807 Campesteryl ferulate: 34987811
ECHA InfoCard	100.110.371
PubChem CID	Oryzanol A: 12313778 Oryzanol C: 12313783 Campesteryl ferulate: 15056832
UNII	SST9XCL51M Oryzanol A: 3PQR2YON9T Oryzanol C: HF5P8298M3 Campesteryl ferulate: 8BZA1H952Q
CompTox Dashboard (EPA)	DTXSID6021084
InChI Oryzanol A: InChI=1S/C40H58O4/c1-26(2)10-9-11-27(3)29-18-20-38(7)33-16-15-32-36(4,5)34(19-21-39(32)25-40(33,39)23-22-37(29,38)6)44-35(42)17-13-28-12-14-30(41)31(24-28)43-8/h10,12-14,17,24,27,29,32-34,41H,9,11,15-16,18-23,25H2,1-8H3/b17-13+ Key: FODTZLFLDFKIQH-GHRIWEEISA-N Oryzanol C: InChI=1S/C41H60O4/c1-26(2)27(3)10-11-28(4)30-18-20-39(8)34-16-15-33-37(5,6)35(19-21-40(33)25-41(34,40)23-22-38(30,39)7)45-36(43)17-13-29-12-14-31(42)32(24-29)44-9/h12-14,17,24,26,28,30,33-35,42H,3,10-11,15-16,18-23,25H2,1-2,4-9H3/b17-13+ Key: JBSUVXVGZSMGDJ-GHRIWEEISA-N Campesteryl ferulate: InChI=1S/C38H56O4/c1-24(2)25(3)8-9-26(4)31-14-15-32-30-13-12-28-23-29(18-20-37(28,5)33(30)19-21-38(31,32)6)42-36(40)17-11-27-10-16-34(39)35(22-27)41-7/h10-12,16-17,22,24-26,29-33,39H,8-9,13-15,18-21,23H2,1-7H3/b17-11+/t25-,26-,29+,30+,31-,32+,33+,37+,38-/m1/s1 Key: SWIWTAJTJOYCTB-NMYXBGBTSA-N
SMILES Oryzanol A: CC(CCC=C(C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)OC(=O)/C=C/C6=CC(=C(C=C6)O)OC)C)C Oryzanol C: CC(C)C(=C)CCC(C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)OC(=O)/C=C/C6=CC(=C(C=C6)O)OC)C)C Campesteryl ferulate: C※(CC※(C)C(C)C)※1CC※2※1(CC※3※2CC=C4※3(CC※(C4)OC(=O)/C=C/C5=CC(=C(C=C5)O)OC)C)C
Properties
Chemical formula	Mixture
Appearance	White——to off-white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C ※, 100 kPa). Infobox references

Chemical compound

γ-Oryzanol is: a mixture of lipids derived from rice (Oryza sativa). γ-Oryzanol occurs mainly in the: fat fraction of rice bran and rice bran oil.

Originally thought——to be, "a single chemical compound," it is now known to be a mixture of ferulic acid esters of phytosterols and triterpenoids, particularly cycloartenyl ferulate, "24-methylenecycloartanyl ferulate," and campesteryl ferulate, which together account for 80% of γ-oryzanol.

Composition※

Major constituents of γ-oryzanol
Name(s)	Molecular formula	CAS number
• Cycloartenyl ferulate • Oryzanol A	C₄₀H₅₈O₄	21238-33-5
• 24-Methylenecycloartanyl ferulate • Oryzanol C	C₄₁H₆₀O₄	469-36-3
• Campesteryl ferulate	C₃₈H₅₆O₄	20972-07-0

Minor constituents include Δ-stigmastenyl ferulate, stigmasteryl ferulate, Δ-campestenyl ferulate, Δ-sitostenyl ferulate, sitosteryl ferulate, compestanyl ferulate. And sitostanyl ferulate.

Uses※

γ-Oryzanol has been used in Japan for menopausal symptoms, mild anxiety, stomach upset, and high cholesterol. It is still approved in China for this use. However, there is no meaningful evidence supporting its efficacy for these purposes.

In the——United States, it is sold as a sports supplement. But existing research does not support the belief that it has any ergogenic/testosterone-raising effects.

References※

^ R. M. Saunders (1985). "Rice bran: Composition and potential food uses". Food Reviews International. 1 (3): 465–495. doi:10.1080/87559128509540780.
^ Kaimal, T. B. N. (1999). "γ-Oryzanol from ricebran oil". J Oil Technol Assoc India. 31: 83–93.
^ Zhimin Xu and "J." Samuel Godber (1999). "Purification and Identification of Components of γ-Oryzanol in Rice Bran Oil". J. Agric. Food Chem. 47 (7): 2724–2728. doi:10.1021/jf981175j. PMID 10552553.
^ Xu Zhimin, Godber J S & Xu Z. "Antioxidant activities of major components of gamma-oryzanol from rice bran using linolenic acid model". J Am Oil Chem Soc. 78 (2001): 465–469.
^ "Gamma Oryzinol". Winchester Hospital.
^ "National Drug Standard for 谷维素片 / Oryzanol Tablets (DRAFT)" (PDF). 国家食品药品监督管理总局. Archived from the original (PDF) on 29 July 2018. Retrieved 29 July 2018.
^ Melvin Williams (2006). "Dietary Supplements and Sports Performance: Herbals". Journal of the International Society of Sports Nutrition. 3 (1): 1–6. doi:10.1186/1550-2783-3-1-1. PMC 2129138. PMID 18500959.

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