58864-81-6

Basic information

• Product Name: D-ALPHA-TOCOTRIENOL
• Synonyms: D-a-Tocotrienol;D-ALPHA-TOCOTRIENOL;(2R,3'E,7'E)-alpha-Tocotrienol;(R)-alpha-Tocotrienol;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9ci);[R-(E,E)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol
• CAS NO: 58864-81-6
• Molecular Formula: C₂₉H₄₄O₂
• Molecular Weight: 424.65846
• Mol File: 58864-81-6.mol

Chemical Properties

• Melting Point: 30-31 °C
• Boiling Point: 541.7±50.0 °C(Predicted)
• Appearance: /
• Density: 0.960±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.40±0.40(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: D-ALPHA-TOCOTRIENOL(CAS DataBase Reference)
• NIST Chemistry Reference: D-ALPHA-TOCOTRIENOL(58864-81-6)
• EPA Substance Registry System: D-ALPHA-TOCOTRIENOL(58864-81-6)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 58864-81-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
D-ALPHA-TOCOTRIENOL is used as a neuroprotective agent for its ability to block glutamate-induced cell death in neuronal cells. This property makes it a promising candidate for the treatment and prevention of neurodegenerative diseases, such as Alzheimer's and Parkinson's disease, where oxidative stress and neuronal cell death are significant factors.
Used in Antioxidant Formulations:
D-ALPHA-TOCOTRIENOL is used as an antioxidant in various industries, including the pharmaceutical, cosmetic, and dietary supplement sectors. Its potent antioxidant properties help neutralize free radicals, reducing the risk of cellular damage and promoting overall health.
Used in Cosmetic Applications:
In the cosmetic industry, D-ALPHA-TOCOTRIENOL is used as an ingredient in skincare products for its antioxidant and anti-aging properties. It helps protect the skin from environmental stressors, such as UV radiation and pollution, and may contribute to the reduction of fine lines, wrinkles, and other signs of aging.
Used in Dietary Supplements:
D-ALPHA-TOCOTRIENOL is used as a dietary supplement to support overall health and well-being. It is often included in multivitamin formulations or marketed as a standalone supplement, particularly for individuals seeking to improve their antioxidant intake and support cognitive function and brain health.

Upstream product

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• 210174-90-6 methyl-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylate 
• 86646-83-5 methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate 
• 56881-53-9 (E,E)-farnesyl phenylsulfone 
• 24163-93-7 farnesyl bromide 
• 56305-04-5 trolox 
• 106-28-5 Farnesol 
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• 1375483-12-7 (2,5,7,8-tetramethyl-chroman-2-yl)methanol 
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Downstream Products

• 916319-75-0 2-[(6E,10E)-3-hydroxy-3,7,11,15-tetramethyl-6,10,14-hexadecatrienyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 
• 1258410-49-9 4-(((R)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-yloxy)carbonyl)isophthalic acid 
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• 1213269-98-7 EPI₇₄₃ 
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• 1208120-80-2 (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl phenylsulfonylcarbamate 
• 1208121-05-4 (R)-6-((3-methoxybenzyl)oxy)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman 
• 1208120-92-6 13(R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl benzylcarbamate 
• 1208120-86-8 (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl 4-chlorophenylsulfonylcarbamate 
• 1208120-89-1 (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl phenylcarbamate 
• 1208120-83-5 (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl tosylcarbamate 
• 1208121-07-6 (R)-6-(3,5-dimethoxybenzyl)oxy-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman 

Relevant articles and documents

CHINONE-, HYDROCHINOME- AND NAPHTHOCHINONE-ANALOGUES OF VATIQUIONE FOR TREATMENT OF MITOCHONDRIAL DISORDER DISEASES

The disclosure provides therapeutic compositions (i.e., therapeutic agents) and methods of preventing or treating Friedreich's ataxia in a mammalian subject, reducing risk factors, signs and/or symptoms associated with Friedreich's ataxia (e.g. Complex I deficiency), and/or reducing the likelihood or severity of Friedreich's ataxia. The disclosure further provides novel intermediates for the production of said therapeutic compositions and related reduced versions of said therapeutic compositions, which reduce forms may also be used as therapeutic agents (or prodrugs of the therapeutic agent(s)).

SYNTHESIS OF TOCOTRIENOLS FROM O-CRESOL DERIVATIVES

The present invention provides an environmentally benign, facile process for preparation of Tocotrienols from commercially available derivatives of o-Cresol.

SEPARATION OF CHIRAL ISOMERS BY SFC

The present invention relates to the field of separating chiral isomers from each other. Particularly, it relates to the field of separating of chiral isomers of chromane or chromene compounds, particularly tocopherols, 3,4-dehydro-tocopherols and tocotrienols, as well as the protected forms thereof. It has been found that the use of supercritical carbon dioxide as mobile phase combined with the very specific chiral phase as stationary phase leads to a very efficient separation of the individual chiral isomers. As the method is very efficient and fast combined with advantageous in view of ecology it is of big industrial interest.

Biomimetic chromanol cyclisation: A common route to a-tocotrienol and α-tocopherol

A common synthetic route to a-tocotrienol and a-tocopherol has been accomplished by a biomimetic cyclisation that yields the chromanol ring. The chirality at C2 of the chro- manol was induced by a covalently attached chiral dipeptide. Its terminal Asp participates in the enantioface-selective pro-tonation of the double bond of the a-tocotrienol precursor. a-Tocotrienol was diastereoselectively hydrogenated to a-tocopherol.

Chemoenzymatic synthesis of both enantiomers of α-tocotrienol

The stereoselective acylation of the achiral chromanedimethanol derivative 1 by vinyl acetate in the presence of Candida antarctica lipase B gave the (S)-monoester 2 in high enantiomeric purity (ee ≥ 98%). Enzymatic hydrolysis of diesters of compound 1 failed to give (R)-monoester 2 in good yield and high ee. Thus, both enantiomers of α-tocotrienol were synthesized from the (S)-monoester 2.