Structure Database (LMSD)

Common Name
alpha-tocotrienol
Systematic Name
2R,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
Synonyms
  • alpha-tocotrienol
  • zeta1-tocopherol
LM ID
LMPR02020054
Formula
Exact Mass
Calculate m/z
424.33413
Status
Curated



Classification

Biological Context

α-Tocotrienol is an antioxidant and a form of vitamin E that has been found in rice bran and has neuroprotective properties.1,2,3,4 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 Cytosolic microinjection of α-tocotrienol prevents glutamate-induced cell death and phosphorylation of 12-lipoxygenase (12-LO) in HT4 neurons.3 It reduces glutamate-induced cytosolic and mitochondrial production of reactive oxygen species (ROS), accumulation of N-terminally truncated Bcl-xL (ΔN-Bcl-xL), and cell death in primary rat hippocampal neurons.4 α-Tocotrienol (50 mg/kg) reduces infarct size in a spontaneously hypertensive rat model of stroke induced by tandem right common carotid artery and middle cerebral artery occlusion.3 [Matreya, LLC. Catalog No. 2109]

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).
4. Park, H.-A., Mnatsakanyan, N., Broman, K., et al. Alpha-tocotrienol prevents oxidative stress-mediated post-translational cleavage of Bcl-xL in primary hippocampal neurons. Int. J. Mol. Sci. 21(1), 220 (2020).

String Representations

InChiKey (Click to copy)
RZFHLOLGZPDCHJ-XZXLULOTSA-N
InChi (Click to copy)
InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1
SMILES (Click to copy)
CC1C(=C(C(=C2O[C@@](C)(CCC=12)CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/C)\C)C)C)O

Other Databases

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 2
Aromatic Rings 1
Rotatable Bonds 9
Van der Waals Molecular Volume 476.38
Topological Polar Surface Area 31.53
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 8.89
Molar Refractivity 134.83

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Updated at
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