1721-51-3

Basic information

• Product Name: (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol
• Synonyms: (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol;tocotrienol, alpha;3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol;5,7,8-Trimethyltocotrienol;ξ1-Tocopherol;ξ1-Tokoferol;C14153;D-α-Tocotrienol,3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol
• CAS NO: 1721-51-3
• Molecular Formula: C₂₉H₄₄O₂
• Molecular Weight: 424.66
• Mol File: 1721-51-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 541.7°Cat760mmHg
• Flash Point: 222.3°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 2.39E-12mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: −20°C
• PKA: 11.40±0.40(Predicted)
• CAS DataBase Reference: (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol(1721-51-3)
• EPA Substance Registry System: (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol(1721-51-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1721-51-3(Hazardous Substances Data)

Usage

Description

(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol, also known as a tocotrienol, is a type of chroman-6-ol derivative with methyl groups at positions 2, 5, 7, and 8, and a farnesyl chain at position 2. (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol has been identified in palm oil derived from Elaeis guineensis.

Uses

Used in Pharmaceutical Industry:
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol is used as a potential therapeutic agent for various health-related applications due to its unique chemical structure and presence in natural sources like palm oil.
Used in Nutritional Supplements:
In the nutritional supplement industry, (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol is used as an additive for its potential health benefits, capitalizing on the natural occurrence of this compound in palm oil.
Used in Cosmetics Industry:
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol may be utilized in the cosmetics industry for its potential antioxidant and anti-aging properties, contributing to the development of skincare products with enhanced efficacy.
Used in Research and Development:
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol is also used in research and development for studying its biological activities, potential health benefits, and possible applications in various fields, including pharmaceuticals, nutraceuticals, and cosmetics.

InChI:InChI=1/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+

Upstream product

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• 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 
• 1174643-53-8 tert-butyldimethyl (((R)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)chroman-6-yl)oxy)silane 
• 188416-13-9 [(S)-6-(tert-Butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethyl-chroman-2-yl]-methanol 
• 1375483-12-7 (2,5,7,8-tetramethyl-chroman-2-yl)methanol 
• 697-82-5 2,3,5-trimethylphenol 
• 90242-77-6 α tocotrienol 
• 1169860-40-5 C₃₉H₅₅ClO₅ 
• 479353-37-2 Acetic acid (S)-6-hydroxy-2-hydroxymethyl-5,7,8-trimethyl-chroman-2-ylmethyl ester 

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 
• 1258410-53-5 2-(((R)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-yloxy)carbonyl)terephthalic acid 
• 1253279-71-8 (R)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-yl benzoylcarbamate 
• 1213269-98-7 EPI₇₄₃ 
• 1208120-95-9 phenyl (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl iminodicarbonate 
• 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 
• 58-95-7 vitamin E acetate 

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)).

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.

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.