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Lipids

Γ-Oryzanol

Другие языки:

Γ-Oryzanol

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γ-Oryzanol
Names
Other names gamma-Oryzanol; gamma-Orizanol
Identifiers
CAS Number	11042-64-1^Y Oryzanol A: 21238-33-5^Y Oryzanol C: 469-36-3^Y Campesteryl ferulate: 20972-07-0^Y
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^Y Oryzanol A: 3PQR2YON9T^Y Oryzanol C: HF5P8298M3^Y Campesteryl ferulate: 8BZA1H952Q^Y
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[C@H](CC[C@@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](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 [77 °F], 100 kPa). Infobox references

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 Δ⁷-stigmastenyl ferulate, stigmasteryl ferulate, Δ⁷-campestenyl ferulate, Δ⁷-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 or testosterone-raising effects.