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D-gamma-Tocotrienol

Product NameD-gamma-Tocotrienol
CAS14101-61-2
MFC28H42O2
MW410.63
EINECS
MOL File14101-61-2.mol

Chemical Properties

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
Major Application	pharmaceutical (small molecule) vitamins, nutraceuticals, and natural products
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 Information

WGK Germany	2
Storage Class	10 - Combustible liquids

Usage And Synthesis

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 developinganticancer andantiproliferative agents againstMCF-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

γ-Tocotrienol’s liposomal formulation, GT3-Nano (20 mol% γ-Tocotrienol), (10 mg/kg, 6 mol%; i.v.; single dose, observed for 100 d) is highly effective in mitigating the marrow-suppressive effects of sublethal and lethal TBI in mice^[3].
GT3-Nano (50 mg/kg; i.v.; ) can facilitate rapid recovery of hematopoietic components in mice treated with the endoradiotherapeutic agent ¹⁵³Sm-EDTMP^[3].

Animal Model:	C57/BL6 mice (6-8 weeks old) treated with the whole-body irradiation^[3]
Dosage:	16, 24, 32, and 50 mg/kg
Administration:	Intravenous injection; observed mice for 100 days
Result:	Demonstrated dose-dependent radioprotection, achieving 90% survival at 50 mg/kg against lethal 9-Gy of total-body irradiation (TBI). And upregulated progenitor bone marrow cells MPP2 and CMP in GT3-Nano-treated mice.

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

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