7559-04-8

Basic information

• Product Name: D-ALPHA-TOCOPHERYLQUINONE
• Synonyms: 2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethyl-p-benzoquinon;alpha-tocopherolquinone;alpha-tocopheroquinone;alpha-tocoquinone;atq;metarene;VITAMINE E-QUINONE;VITAMIN E QUINONE
• CAS NO: 7559-04-8
• Molecular Formula: C₂₉H₅₀O₃
• Molecular Weight: 446.71
• EINECS: 231-450-8
• Product Categories: Benzoquinones;Biochemistry;Vitamins
• Mol File: 7559-04-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 496°C (rough estimate)
• Flash Point: 291.9 °C
• Appearance: Clear amber to red/Viscous Liquid
• Density: 1.0115 (rough estimate)
• Vapor Pressure: 1.02E-13mmHg at 25°C
• Refractive Index: 1.492-1.496
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 14.99±0.29(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: D-ALPHA-TOCOPHERYLQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: D-ALPHA-TOCOPHERYLQUINONE(7559-04-8)
• EPA Substance Registry System: D-ALPHA-TOCOPHERYLQUINONE(7559-04-8)

Safety Data

• Safety Statements: 24/25
• RTECS: DK5170000
• Hazardous Substances Data: 7559-04-8(Hazardous Substances Data)

Usage

Chemical Properties

clear amber viscous liquid

Uses

D-α-Tocopherol Quinone is an vitamin E derivative that exhibits antioxidant properties.?D-α-Tocopherol Quinone has been shown to partially restore the activity of NADH dehydrogenase and used to investigate the electron transport system in rat hepatocyte and human erythrocyte.

InChI:InChI=1/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3/t21-,22-,29-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 7705-08-0 iron(III) chloride 
• 59-02-9 Tocopherol 
• 527-18-4 Durohydroquinone 
• 527-17-3 Duroquinone 
• 13199-54-7 1,4-dimethoxy-2,3,5,6-tetramethylbenzene 
• 91418-95-0 (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol 
• 10191-41-0 (+/-)-α-tocopherol 
• 59-02-9 d-α-Tocopherol, E 
• 88083-17-4 2-Methyl-2-[2,5,7,8-tetramethyl-6-oxo-2-(4,8,12-trimethyl-tridecyl)-2,3,4,6-tetrahydro-chromen-8a-ylperoxy]-propionic acid butyl ester 
• 88056-74-0 2-Methyl-2-[2,5,7,8-tetramethyl-6-oxo-2-(4,8,12-trimethyl-tridecyl)-2,3,4,6-tetrahydro-chromen-8a-ylperoxy]-propionitrile 
• 197297-77-1 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)butan-2-one 
• 131426-03-4 1-iodo-2,5-bis(methoxy)-3,4,6-trimethylbenzene 
• 16825-16-4 (6R,10R)-6,10,14-trimethylpentadecan-2-one 

Downstream Products

• 91418-95-0 (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol 
• 916319-64-7 (R/S,R,R)-2,3,5-trimethyl-6-(3,7,11,15-tetramethyl-hexadecyl)-benzene-1,4-diol 
• 59-02-9 Tocopherol 
• 18920-63-3 vitamin E 
• 129658-44-2 3-((3R,7R,11R)-3-Hydroxy-3,7,11,15-tetramethyl-hexadecyl)-2,4,5,6-tetramethyl-phenol 
• 10191-41-0 (+/-)-α-tocopherol 
• 14745-36-9 2-((7R,11R)-3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylbenzene-1,4-diol 

Relevant articles and documents

Modulation of the mitochondrial cytochrome bc1 complex activity by chromanols and related compounds

Tocopherols (α-, β-, γ-, and δ-Toc) and tocopheryl quinones (α-, β-, γ-, and δ-TQ) were recently suggested to modulate mitochondrial electron transfer in mammals. Intriguingly, Tocs and stigmatellin, a potent inhibitor of the mitochondrial cytochrome (cyt) bc 1 complex, possess a common structural feature: the chroman core. Therefore, we studied the interference of Tocs as well as synthetic model compounds (low molecular weight TQ analogues and tetramethyl chromanones) at the mitochondrial cyt bc1 complex. Enzymatic experiments revealed that besides the inhibitor stigmatellin, among natural vitamin E-related derivatives, γ-TQ/δ-TQ and, among synthetic compounds, TMC2O (6-hydroxy-4,4,7,8-tetramethylchroman-2-one) were most effective in decreasing the cyt bc1 activities. Stopped-flow photometric and low-temperature electron paramagnetic resonance spectroscopic experiments showed for TMC2O an inhibition of electron transfer to cyt c1 and a modulation of the environment of the Rieske iron - sulfur protein (ISP). Docking experiments suggest a binding interaction of the 6-OH group and 1-O atom/2-C( = O) group of TMC2O with Glu-271 (cyt b) and His-161 (ISP) in the cyt bc1 complex, respectively. This binding pose is similar but not identical to the potent inhibitor stigmatellin. The data suggest that chroman-2-ones are possible templates for modulatory molecules for the cyt bc1 target.

QUINONES AND PROCESS OF OBTAINING SAME

Disclosed is a process for the oxidation of at least one chroman (C1) in a solvent mixture comprising at least two solvents or in a C-bearing solvent, with a gaseous compound comprising, essentially consisting of, or consisting of oxygen in the presence of a copper catalyst, said copper catalyst exhibiting the oxidation state (+1) or (+2). A further part of the disclosure is a composition comprising at least one chroman (C1) and/or at least one quinone (C30), a solvent mixture comprising at least two solvents or a C-bearing solvent, a copper catalyst, said copper catalyst exhibiting the oxidation state (+1) or (+2) and a gaseous compound comprising, essentially consisting or consisting of oxygen. A quinone preparation and a process of making same is also part of the invention.

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.