ChemicalBook--->CAS DataBase List--->14101-61-2

14101-61-2

14101-61-2 Structure

14101-61-2 Structure
IdentificationBack Directory
[Name]

D-gamma-Tocotrienol
[CAS]

14101-61-2
[Synonyms]

D-G-TOCOTRIENOL
Gama-Tocotrienol
D-GAMMA-TOCOTRIENOL
(R)-gamma-Tocotrienol
7,8-Dimethyltocotrienol
6-Chromanol, 2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)- (7ci,8ci)
(R-(E,E))-3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol
(R)-3,4-Dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-2H-1-benzopyran-6-ol
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-
(2R)-2β,7,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-3,4-dihydro-2H-1-benzopyran-6-ol
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-
2H-1-Benzopyran-6-ol,3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-,(2R)-
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-tr imethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)
(R-(all-E))-3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12,16,20,24,28,32-octamethyl-3,7,11,15,19,23,27,31-tritriacontaoctaenyl)-2H-1-benzopyran-6-ol
[Molecular Formula]

C28H42O2
[MDL Number]

MFCD05864856
[MOL File]

14101-61-2.mol
[Molecular Weight]

410.63
Chemical PropertiesBack Directory
[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 ]

neat
[pka]

11.05±0.40(Predicted)
[color ]

Very Dark Yellow Thick
[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 DataBack Directory
[WGK Germany ]

2
[Storage Class]

10 - Combustible liquids
Hazard InformationBack Directory
[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 (Item No. 82220), or L-buthionine-(S,R)-sulfoximine (BSO; Item No. 14484) 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]

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
Spectrum DetailBack Directory
[Spectrum Detail]

D-gamma-Tocotrienol(14101-61-2)1HNMR
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