91418-95-0

Basic information

• Product Name: (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol
• Synonyms: (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol
• CAS NO: 91418-95-0
• Molecular Weight: 476.784
• Mol File: 91418-95-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol(91418-95-0)
• EPA Substance Registry System: (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol(91418-95-0)

Safety Data

• Hazardous Substances Data: 91418-95-0(Hazardous Substances Data)

Upstream product

• 131426-03-4 1-iodo-2,5-bis(methoxy)-3,4,6-trimethylbenzene 
• 150-86-7 phytol 
• 16825-16-4 (6R,10R)-6,10,14-trimethylpentadecan-2-one 
• 82299-54-5 2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethylmagnesium bromide 
• 4537-09-1 1,4-dimethoxy-2,3,5-trimethyl-benzene 
• 197297-77-1 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)butan-2-one 
• 114341-71-8 (4R,8R)-1-Bromo-4,8,12-trimethyltridecane 
• 87247-35-6 (4R,8R)-4,8,12-trimethyltridecan-1-ol 
• 917-64-6 methyl magnesium iodide 
• 58-95-7 RRR-α-tocopheryl acetate 
• 59-02-9 Tocopherol 
• 14745-36-9 2-((7R,11R)-3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylbenzene-1,4-diol 
• 77-78-1 dimethyl sulfate 
• 7559-04-8 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 

Downstream Products

• 7559-04-8 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 
• 14745-36-9 2-((7R,11R)-3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylbenzene-1,4-diol 
• 59-02-9 Tocopherol 

Relevant articles and documents

Highly stereoselective construction of the C2 stereocentre of α-tocopherol (Vitamin E) by asymmetric addition of Grignard reagents to ketones

Tertiary alcohol precursors of both C2 diastereoisomers of α-tocopherol were prepared in three ways by our recently reported asymmetric Grignard synthesis. The versatility of Grignard chemistry inherent in its three-way disconnection was exploited to allow the synthesis of three product grades: 77:23 dr (5 steps), 81:19 dr (5 steps) and 96:4 dr (7 steps, one gram scale) from readily available and abundant starting materials. The products were converted to their respective α-tocopherols in 3 steps, which allowed a definitive re-assignment of their absolute configurations.

Towards a modern definition of vitamin e - Evidence for a quinone hypothesis

We report on the synthesis, biological and pharmacological activity of the tocoquinone natural product, α-tocopherol quinone (ATQ); an oxidative metabolite of α-tocopherol. ATQ is a potent cellular protectant against oxidative stress, whose biological activity is dependent upon its ability to undergo reversible two-electron redox cycling. ATQ is orally bioavailable, with a favorable pharmacokinetic profile and has demonstrated a beneficial clinical response in patients with Friedreich's ataxia. ATQ is a member of a broader class of vitamin E derived quinone metabolites which may be ascribable in whole or in part to the activity of vitamin E.

Hydroquinone derivatives useful in the production of vitamin E

The present invention is directed to novel hydroquinone derivatives which are useful as intermediates for the manufacture of (R,R,R)-α-tocopherol (natural vitamin E) as well as of racemic α-tocopherol. The invention is also directed to a process for the preparation of the hydroquinone derivatives of the invention.