γ-Oryzanol

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γ-Oryzanol
Names
Other names
gamma-Oryzanol; gamma-Orizanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.110.371 Edit this at Wikidata
UNII
  • 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
  • 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
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).

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[edit]

Major constituents of γ-oryzanol
Names Chemical structure Molecular formula CAS number
Cycloartenyl ferulate
Oryzanol A
Cycloartenyl ferulate.svg C40H58O4 21238-33-5
24-Methylenecycloartanyl ferulate
Oryzanol C
24-Methylenecycloartanyl ferulate.svg C41H60O4 469-36-3
Campesteryl ferulate Campesterol ferulate.svg 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[edit]

γ-Oryzanol has been used in Japan for menopausal symptoms, mild anxiety, stomach upset, and high cholesterol.[5] 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.[6]

References[edit]

  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.
  3. ^ 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.
  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.
  5. ^ a b "Gamma Oryzinol". Winchester Hospital.
  6. ^ 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.