γ-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[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).^[1] γ-Oryzanol occurs mainly in the fat fraction of rice bran and rice bran oil.

Originally thought to be a single chemical compound,^[2] 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,^[3] which together account for 80% of γ-oryzanol.^[4]

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.^[3]

Uses

γ-Oryzanol has been used in Japan for menopausal symptoms, mild anxiety, stomach upset, and high cholesterol.^[5] It is still approved in China for this use.^[6] However, there is no meaningful evidence supporting its efficacy for these purposes.^[5]

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.^[7]

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.
^ ^a ^b 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 a linolenic acid model". J Am Oil Chem Soc. 78 (2001): 465–469.
^ ^a ^b "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.

[1] R. M. Saunders (1985). "Rice bran: Composition and potential food uses". Food Reviews International. 1 (3): 465–495. doi:10.1080/87559128509540780.

[2] Kaimal, T. B. N. (1999). "γ-Oryzanol from ricebran oil". J Oil Technol Assoc India. 31: 83–93.

[Godber-3] 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.

[4] Xu Zhimin, Godber J S & Xu Z. "Antioxidant activities of major components of gamma-oryzanol from rice bran using a linolenic acid model". J Am Oil Chem Soc. 78 (2001): 465–469.

[WH-5] "Gamma Oryzinol". Winchester Hospital.

[6] "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.

[7] 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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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