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Structure Database (LMSD)

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Common Name

gamma-tocotrienol

Systematic Name

2R,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol

Synonyms

LM ID

LMPR02020057

Formula

C₂₈H₄₂O₂

Exact Mass

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410.31848

Status

Curated

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Classification

Biological Context

γ-Tocotrienol is a form of vitamin E that has been found in rice bran and has diverse biological activities.^1,2 It reduces cell death induced by hydrogen peroxide, paraquat, S-nitrocysteine, SIN-1 , or L-buthionine-(S,R)-sulfoximine (BSO) in rat striatal cultures when used at concentrations ranging from 0.1 to 10 µM.² γ-Tocotrienol (20 µM) induces apoptosis in malignant sympathoadrenal (+SA) mouse mammary epithelial cells.³ In vivo, γ-tocotrienol (15, 30, and 150 mg/kg) reduces blood pressure and plasma lipid peroxide levels in spontaneously hypertensive rats.⁴ [Matreya, LLC. Catalog No. 2111]

This information has been provided by Cayman Chemical

References

1. Kamal-Eldin, A., and Appelqvist, L.-Å. The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31(7), 671-701 (1996).

2. Osakada, F., Hashino, A., Kume, T., et al. α-Tocotrienol provides the most potent neuroprotection among vitamin E analogs on cultured striatal neurons. Neuropharmacology 47(6), 904-915 (2004).

3. Shah, S., and Sylvester, P.W. Tocotrienol-induced caspase-8 activation is unrelated to death receptor apoptotic signaling in neoplastic mammary epithelial cells. Exp. Biol. Med. (Maywood) 229(8), 745-755 (2004).

4. Newaz, M.A., Yousefipour, Z., Nawal, N., et al. Nitric oxide synthase activity in blood vessels of spontaneously hypertensive rats: Antioxidant protection by γ-tocotrienol. J. Physiol. Pharmacol. 54(3), 319-327 (2003).

String Representations

InChiKey (Click to copy)

OTXNTMVVOOBZCV-WAZJVIJMSA-N

InChi (Click to copy)

InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1

SMILES (Click to copy)

C1C(=C(C(=C2O[C@@](C)(CCC=12)CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/C)\C)C)C)O