D-gamma-Tocotrienol

D-gamma-Tocotrienol Property

Boiling point:

530.8±49.0 °C(Predicted)

Density 

0.964±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Liquid

pka

11.05±0.40(Predicted)

color 

Very Dark Yellow

biological source

Elaeis guineensis

Stability:

Light Sensitive

InChIKey

OTXNTMVVOOBZCV-WAZJVIJMSA-N

SMILES

[C@@]1(C)(CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/C)OC2=C(C)C(C)=C(O)C=C2CC1

LogP

10.300 (est)

Safety

WGK Germany 

2

Hazard and Precautionary Statements (GHS)

D-gamma-Tocotrienol Chemical Properties,Usage,Production

Description

γ-Tocotrienol is a form of vitamin E that has been found in rice bran and has diverse biological activities. 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. γ-Tocotrienol (20 μM) induces apoptosis in malignant sympathoadrenal (+SA) mouse mammary epithelial cells. In vivo, γ-tocotrienol (15, 30, and 150 mg/kg) reduces blood pressure and plasma lipid peroxide levels in spontaneously hypertensive rats. [Matreya, LLC. Catalog No. 2111]

Chemical Properties

g:d:aTocotrienol 1.6:0.4:1

Uses

γ-Tocotrienol exhibits antioxidant properties and belongs to the vitamin E family. It is naturally found in wheat germ oil and bran. In addition, α-tocopherol and γ-tocotrienol derivatives are potential lead compounds for developing?anticancer and?antiproliferative agents against?MCF-7 and MDA-MB-231 breast cancer cells and the A549 lung cancer cells.

Definition

ChEBI: A tocotrienol that is chroman-6-ol substituted by methyl groups at positions 2, 7 and 8 and a farnesyl chain at position 2.

in vivo

References

[1] AFAF KAMAL-ELDIN  Lars ? A. The chemistry and antioxidant properties of tocopherols and tocotrienols[J]. Lipids, 1996, 31 7: 671-701. DOI: 10.1007/bf02522884
[2] FUMITAKA OSAKADA . α-Tocotrienol provides the most potent neuroprotection among vitamin E analogs on cultured striatal neurons[J]. Neuropharmacology, 2004, 47 6: Pages 904-915. DOI: 10.1016/j.neuropharm.2004.06.029
[3] SUMIT SHAH  Paul W S. Tocotrienol-induced caspase-8 activation is unrelated to death receptor apoptotic signaling in neoplastic mammary epithelial cells.[J]. Experimental Biology and Medicine, 2004, 229 8: 745-755. DOI: 10.1177/153537020422900806
[4] M A NEWAZ. Nitric oxide synthase activity in blood vessels of spontaneously hypertensive rats: antioxidant protection by gamma-tocotrienol.[J]. Journal of Physiology and Pharmacology, 2003, 54 3: 319-327.
[5] MATTHEW J. KUHN  Lorraine M S. Inhibition of 20-hydroxyeicosatetraenoic acid biosynthesis by vitamin E analogs in human and bovine cytochrome P450 microsomes[J]. Journal of Animal Physiology and Animal Nutrition, 2021, 106 1: 55-60. DOI: 10.1111/jpn.13547
[6] M.J. KUHN  L. M S. Vitamin E analogs limit in vitro oxidant damage to bovine mammary endothelial cells[J]. Journal of Dairy Science, 2021, 104 6: Pages 7154-7167. DOI: 10.3168/jds.2020-19675