delta-Tocotrienol

Base Information

• Chemical Name: delta-Tocotrienol
• CAS No.: 25612-59-3
• Molecular Formula: C₂₇H₄₀O₂
• Molecular Weight: 396.613
• Hs Code.: 29061990
• European Community (EC) Number: 607-758-7
• UNII: 1SRB74OWSI
• DSSTox Substance ID: DTXSID30180288
• Nikkaji Number: J17.358D
• Wikidata: Q27104272
• NCI Thesaurus Code: C116743
• Metabolomics Workbench ID: 29100
• ChEMBL ID: CHEMBL121305
• Mol file: 25612-59-3.mol

Synonyms:delta-tocotrienol;tocotrienol, delta

Chemical Property of delta-Tocotrienol

Chemical Property:

• Vapor Pressure: 2.54E-11mmHg at 25°C
• Boiling Point: 517.3°Cat760mmHg
• PKA: 10.69±0.40(Predicted)
• Flash Point: 212.8°C
• PSA: 29.46000
• Density: 0.968g/cm³
• LogP: 7.98370
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 8.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 396.302830514
• Heavy Atom Count: 29
• Complexity: 596

Purity/Quality:

98%Min ^*data from raw suppliers

δ-Tocotrienol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=CC2=C1OC(CC2)(C)CCC=C(C)CCC=C(C)CCC=C(C)C)O
• Isomeric SMILES: CC1=CC(=CC2=C1O[C@](CC2)(C)CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)O
• Uses: δ-Tocotrienol is a natural substance with vitamin E activity. It can work as an antioxidant. It inhibits the growth of human breast cancer cells.

Technology Process of delta-Tocotrienol

There total 18 articles about delta-Tocotrienol 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: 85.0%

t-butyl-[(R)-2,8-dimethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-yloxy]dimethylsilane → delta-tocotrienol (14101-60-1,25612-59-3,136845-52-8,1175-39-9)

Guidance literature:

With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; at 25 ℃; for 2h;

Reference yield: 75.0%

2'-phenylsulfonyl-δ-tocotrienyl benzyl ether (951404-44-7) → delta-tocotrienol (14101-60-1,25612-59-3,136845-52-8,1175-39-9)

Guidance literature:

With lithium; methylamine; In diethyl ether; at -78 ℃; for 0.75h;

DOI:10.1021/jo0705418

Reference yield:

(S)-2-hydroxymethyl-2,8-dimethylchroman-6-ol (951404-39-0) → delta-tocotrienol (14101-60-1,25612-59-3,136845-52-8,1175-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 73 percent / K₂CO₃ / dimethylformamide / 12 h

2.1: 95 percent / pyridine / 2 h

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

3.2: 60 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

4.1: 75 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-δ-tocotrienyl benzyl ether

methyl 2,8-dimethyl-6-benzoyloxychroman-2-carboxylate

2,8-dimethyl-6-hydroxychroman-2-methanol

C₁₆H₂₀O₆

Downstream raw materials:

(R)-2,8-dimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl tosylcarbamate

(R)-2,8-dimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl phenylcarbamate

(R)-2,8-dimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl 4-chlorophenylsulfonylcarbamate

(R)-2,8-dimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl benzylcarbamate

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.