72657-56-8

Basic information

• Product Name: α-tocopherolquinone
• CAS NO: 72657-56-8
• Molecular Weight: 446.714
• Mol File: 72657-56-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: α-tocopherolquinone(CAS DataBase Reference)
• NIST Chemistry Reference: α-tocopherolquinone(72657-56-8)
• EPA Substance Registry System: α-tocopherolquinone(72657-56-8)

Safety Data

• Hazardous Substances Data: 72657-56-8(Hazardous Substances Data)

Upstream product

• 69371-91-1 2,3,6-trimethyl-5-(3-hydroxy-3,7,11,15-tetramethylhexadecanyl)phenol 
• 59-02-9 vitamin E 
• 110-86-1 pyridine 
• 187806-29-7 [6-Hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-yl]methyl bromide 
• 121-44-8 triethylamine 
• 845-30-7 m-chlorobenzoyl peroxide 
• 59-02-9 Tocopherol 
• 71-43-2 benzene 
• 94-36-0 dibenzoyl peroxide 
• 66074-00-8 3,4-bis(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide 
• 502-69-2 6,10,14-Trimethyl-2-pentadecanon 
• 69371-90-0 7-hydroxy-7,11,15,19-tetramethyleicosane-2,4-dione 
• 69371-89-7 1,2-epoxy-2,6,10,14-tetramethylpentadecane 
• 69371-88-6 dimethyl 2-hydroxy-4-methyl-6-(3-hydroxy-3,7,11,15-tetramethylhexadecanyl)benzene-1,3-dicarboxylate 

Downstream Products

• 10191-41-0 (+/-)-α-tocopherol 
• 129658-44-2 3-((3R,7R,11R)-3-Hydroxy-3,7,11,15-tetramethyl-hexadecyl)-2,4,5,6-tetramethyl-phenol 
• 107781-11-3 C₈H₁₂NiC₆(CH₃)3(C₂₀H₄₁O)O₂ 

Relevant articles and documents

Design, synthesis, and biological characterization of potential antiatherogenic nitric oxide releasing tocopherol analogs

Synthesis and biological characterization of a series of α-tocopherol analogs with NO-releasing capacity are reported. The selected NO-donor moieties were nitrooxy and furoxan. All products were tested for their in vitro NO-releasing capacities, vasodilat

Nitric oxide-induced oxidation of α-tocopherol

Exposure of α-tocopherol (α-T) to nitric oxide under aerobic conditions resulted in a complex oxidation process whose final outcome was dictated by the nature of the reaction medium. In a cyclohexane solution, a prevailing route led to a mixture of relatively unstable polar products positive to Griess reagent. On standing at room temperature these were partially converted to the novel 2,3-dimethyl-4-acetyl-4-hydroxy-5-nitroso-2-cyclopentenone derivative. Reaction of α-T via a secondary oxidation path led to the formation of α-tocopherylquinone (α-TQ) as well as of little amounts of the corresponding nitrite ester. A quite different product pattern was observed when the reaction was carried out on a suspension of α-T in 0.1 M phosphate buffer, pH 7.4. Besides a significant formation of α-TQ and its nitrite ester, product analysis revealed a characteristic pattern of apolar compounds consisting of a yellow dimer and a series of related oligomers. These results provide an improved chemical background to inquire into the role of α-T in nitric oxide-induced tissue injury.

A New Synthesis of α-Tocopherol

α-Tocopherol (vitamin E,1) has been synthesized in racemic form following a new strategy in which the aromatic ring of the chroman is constructed by addition of the dianion of 2,4-pentanedione to 1,2-epoxy-2,6,10,14-tetramethylpentadecane (5) as a side-ch