Structure Database (LMSD)

Common Name
delta-tocotrienol
Systematic Name
2R,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
Synonyms
  • delta-tocotrienol
LM ID
LMPR02020056
Formula
Exact Mass
Calculate m/z
396.30283
Status
Curated



Classification

Biological Context

δ-Tocotrienol is a form of vitamin E that has been found in rice bran and has diverse biological activities.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 δ-Tocotrienol (10 µM) reduces 25-hydroxycholesterol-induced surface expression of VCAM-1 in human aortic endothelial cells (HAECs), as well as reduces 25-hydroxycholesterol-induced HAEC adhesion to U937 monocytes.3 It inhibits LPS-induced production of nitric oxide (NO), TNF-α, IL-6, IL-1β, and IFN-γ in RAW 264.7 cells. δ-Tocotrienol (60 mg/kg) increases the glomerular filtration rate and decreases renal malondialdehyde (MDA) levels in a rat model of nephrotoxicity induced by ochratoxin A .5 [Matreya, LLC. Catalog No. 2112]

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).
3. Naito, Y., Shimozawa, M., Kuroda, M., et al. Tocotrienols reduce 25-hydroxycholesterol-induced monocyte-endothelial cell interaction by inhibiting the surface expresion of adhesion molecules. Atherosclerosis 180, 19-25 (2005).

String Representations

InChiKey (Click to copy)
ODADKLYLWWCHNB-LDYBVBFYSA-N
InChi (Click to copy)
InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1
SMILES (Click to copy)
C1C(=CC(=C2O[C@@](C)(CCC=12)CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/C)\C)C)O

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 2
Aromatic Rings 1
Rotatable Bonds 9
Van der Waals Molecular Volume 441.78
Topological Polar Surface Area 31.53
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 8.27
Molar Refractivity 125.36

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Updated at
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