2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

Base Information

• Chemical Name: 2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
• CAS No.: 7559-04-8
• Molecular Formula: C29H50O3
• Molecular Weight: 446.714
• Hs Code.: 29146990
• European Community (EC) Number: 231-450-8
• NSC Number: 20810
• DSSTox Substance ID: DTXSID30864091
• Nikkaji Number: J2.039.744F
• Wikidata: Q105157204
• Metabolomics Workbench ID: 46526
• ChEMBL ID: CHEMBL1254448
• Mol file: 7559-04-8.mol

Synonyms:2 (3-hydroxy-3,7,11,15-tetramethylhexadecyl)- 3,5,6-trimethyl-1,4-benzoquinone;alpha-tocopherol quinone;alpha-tocopherolquinone;alpha-tocopheryl quinone;alpha-tocoquinone;delta-tocopherylquinone;Eutrophyl;gamma-tocopherylquinone;tocopherolquinone;tocopherylquinone;tocopherylquinone, ((3R*,7R*,11R*)-(+-))-isomer;vitamin E quinone

Chemical Property of 2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

Chemical Property:

• Appearance/Colour: clear amber viscous liquid
• Vapor Pressure: 1.02E-13mmHg at 25°C
• Refractive Index: 1.492-1.496
• Boiling Point: 535.8 °C at 760 mmHg
• PKA: 14.99±0.29(Predicted)
• Flash Point: 291.9 °C
• PSA: 54.37000
• Density: 0.947 g/cm³
• LogP: 7.76140
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 446.37599545
• Heavy Atom Count: 32
• Complexity: 697

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-α-TocopherolQuinone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)C)CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O)C
• Recent ClinicalTrials: Safety and Efficacy Study of A0001 in Subjects With Friedreich's Ataxia
• Recent EU Clinical Trials: A Phase 2a, Double Blind, Randomized, Placebo-controlled, 28 day, Two-arm, Parallel Group Study of A0001 in Patients with the A3243G Mitochondrial DNA Point Mutation and Evidence of Impaired Mitochondrial Function
• 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.

Technology Process of 2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

There total 50 articles about 2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

Tocopherol (59-02-9,18920-62-2) → 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione (7559-04-8)

Guidance literature:

With bromine; In ethanol; at 0 - 20 ℃; for 1.16667h; pH=6; Solvent; Time; Temperature; pH-value; Mechanism; aq. phosphate buffer;

DOI:10.1002/ejoc.201100153

Reference yield: 81.0%

(2R,4'R,8'R)-α-tocopheryl methyl ether (32466-45-8) → 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione (7559-04-8)

Guidance literature:

With dihydrogen peroxide; In ethanol; water; at 25 ℃; for 48h;

DOI:10.1002/adsc.200700340

Reference yield: 47.0%

Tocopherol (59-02-9,18920-62-2) → 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione (7559-04-8) + 5,6-epoxy-α-tocopherylquinone (128359-83-1,128442-21-7,131175-55-8) + 2,3-epoxy-α-tocopherylquinone (212852-38-5) + <8a(S),2'(S)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone (121250-09-7)

Guidance literature:

With 2,2'-azobis-(2,4-dimethylvaleronitrile); water; oxygen; In acetonitrile; at 50 ℃; for 2h; Further byproducts given;

DOI:10.1021/ja00175a037

upstream raw materials:

Tocopherol

(3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol

1,2-dilinolenoyl-sn-glycero-3-phosphocholine

ethanol

Downstream raw materials:

2-((7R,11R)-3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylbenzene-1,4-diol

Tocopherol

(3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol

(R/S,R,R)-2,3,5-trimethyl-6-(3,7,11,15-tetramethyl-hexadecyl)-benzene-1,4-diol

Refernces

• 1、 Karrer,Geiger. "-". . p. 455,457-459. Retrieved 1940.
• 2、 Hinman, Andrew,Holst, Charles R.,Latham, Joey C.,Bruegger, Joel J.,Ulas, G?zde,McCusker, Kevin P.,Amagata, Akiko,Davis, Dana,Hoff, Kevin G.,Kahn-Kirby, Amanda H.,Kim, Virna,Kosaka, Yuko,Lee, Edgar,Malone, Stephanie A.,Mei, Janet J.,Richards, Steve James,Rivera, Veronica,Miller, Guy,Trimmer, Jeffrey K.,Shrader, William D.. "Vitamin E hydroquinone is an endogenous regulator of ferroptosis via redox control of 15-lipoxygenase". . . Retrieved 2018/09/27.
• 3、 Yamauchi, Ryo,Watanabe, Siori,Martín, Ana S,Iwamoto, Satoshi. "Effect of α-tocopherol on the hemin-catalyzed decomposition of 1-palmitoyl-2-linoleoyl-3-sn-phosphatodylcholine 13-hydroperoxide in micelles and liposomes". . p. 61 - 68. Retrieved 2015/01/16.