Showing Metabocard for gamma-tocotrienol (BASm0001875)

Common NameGamma-tocotrienol
Descriptiongamma-Tocotrienol, also known as 7,8-dimethyltocotrienol, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, gamma-tocotrienol is considered to be a quinone lipid molecule. gamma-Tocotrienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Tocotrienol targets cancer cells by inhibiting Id1, a key cancer-promoting protein. gamma-Tocotrienol was shown to trigger cell apoptosis and well as anti-proliferation of cancer cells. This mechanism was also observed in separate prostate cancer and melanoma cell line studies.
Structure
Molecular FormulaC28H42O2
Average Mass410.63190
Monoisotopic Mass410.31848
IUPAC Name(2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional NameGamma-tocotrienol
CAS Registry Number14101-61-2
SMILESCC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCc2cc(O)c(C)c(C)c2O1
InChI IdentifierInChI=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
InChI KeyOTXNTMVVOOBZCV-WAZJVIJMSA-N
CHEBI IDCHEBI:33277
HMDB IDHMDB0012958
StateNot Available
Water Solubility3.40e-04 g/l
logP7.71
logS-6.08
pKa (Strongest Acidic)10.47
pKa (Strongest Basic)-4.85
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area29.46 Ų
Rotatable Bond Count9
Physiological Charge0
Formal Charge0
Refractivity132.88 m³·mol⁻¹
Polarizability52.49

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