2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

Base Information

• Chemical Name: 2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
• CAS No.: 490-23-3
• Molecular Formula: C28H42 O2
• Molecular Weight: 410.64
• Nikkaji Number: J37.066E,J578.420D
• Metabolomics Workbench ID: 44453
• ChEMBL ID: CHEMBL345478
• Mol file: 490-23-3.mol

Synonyms:beta-Tocotrienol-d6;epsilon-Tokoferol;beta-Tocotienol;e-tocopherol;(-)-beta-Tocotrienol;CHEMBL345478;2,5,8-trimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-ol;(2R)-2,5,8-Trimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol;2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol;3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-4H-1-benzopyran-6-ol, 9CI;3,4-Dihydro-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-2H-1-benzopyran-6-ol

Chemical Property of 2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

Chemical Property:

• Vapor Pressure: 8.44E-12mmHg at 25°C
• Melting Point: <25℃
• Boiling Point: 528.8°Cat760mmHg
• PKA: 11.05±0.40(Predicted)
• Flash Point: 217°C
• PSA: 29.46000
• Density: 0.964g/cm³
• LogP: 8.29210
• Storage Temp.: ?20°C
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 410.318480578
• Heavy Atom Count: 30
• Complexity: 625

Purity/Quality:

99% ^*data from raw suppliers

β-Tocotrienol analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C2=C1OC(CC2)(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C)O
• Isomeric SMILES: CC1=CC(=C(C2=C1OC(CC2)(C)CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)C)O
• Uses: β-Tocotrienol is an isomer of Vitamin E. β-Tocotrienol is one of the naturally occurring forms of vitamin E. β-Tocotrienol was isolated from wheat germ oil and from bran.

Technology Process of 2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

There total 19 articles about 2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol 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: 84.0%

2'-phenylsulfonyl-β-tocotrienyl benzyl ether (951404-42-5) → epsilon-tocopherol (490-23-3)

Guidance literature:

With lithium triethylborohydride; palladium bis [1,3-bis(diphenylphosphino)propane]; In tetrahydrofuran;

Reference yield: 76.0%

tert-butyldimethyl [(R)-2,5,8-trimethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-yloxy]silane (1174643-59-4) → epsilon-tocopherol (490-23-3)

Guidance literature:

With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; at 25 ℃; for 1h;

Reference yield:

(S)-2-hydroxymethyl-2,5,8-trimethylchroman-6-ol (850132-70-6) → epsilon-tocopherol (490-23-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 72 percent / K₂CO₃ / dimethylformamide / 12 h

2.1: 96 percent / pyridine / 2 h

3.1: n-butyllithium; HMPA / tetrahydrofuran; hexane / 0.75 h / -78 °C

3.2: 62 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

4.1: 72 percent / Li; MeNH₂ / diethyl ether / 0.75 h / -78 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium; potassium carbonate; methylamine; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo0705418

upstream raw materials:

2'-phenylsulfonyl-β-tocotrienyl benzyl ether

methyl 2,5,8-trimethyl-6-benzoyloxychroman-2-carboxylate

2,5,8-trimethyl-6-hydroxychroman-2-methanol

C₁₇H₂₂O₆

Refernces

• 1、 Couladouros, Elias A.,Moutsos, Vassilios I.,Lampropoulou, Maria,Little, James L.,Hyatt, John A.. "A short and convenient chemical route to optically pure 2-methyl chromanmethanols. Total asymmetric synthesis of β-, γ-, and δ-tocotrienols". . p. 6735 - 6741. Retrieved 2008/02/11.