2-Methyl-6-geranylgeranyl-1,4-benzoquinol

Base Information

• Chemical Name: 2-Methyl-6-geranylgeranyl-1,4-benzoquinol
• CAS No.: 57576-81-5
• Molecular Formula: C27H40O2
• Molecular Weight: 396.613
• DSSTox Substance ID: DTXSID501119085
• Metabolomics Workbench ID: 167229
• Nikkaji Number: J2.213.319E
• Wikidata: Q27145289
• Mol file: 57576-81-5.mol

Synonyms:2-methyl-6-geranylgeranyl-1,4-benzoquinol;MGGBQ;6-geranylgeranyl-2-methylbenzene-1,4-diol;SCHEMBL4614966;SCHEMBL4807578;CHEBI:75411;DTXSID501119085;57576-81-5;C20737;Q27145289;2-Methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-yl]-1,4-benzenediol;2-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol;2-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]benzene-1,4-diol

Chemical Property of 2-Methyl-6-geranylgeranyl-1,4-benzoquinol

Chemical Property:

• XLogP3: 9.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 396.302830514
• Heavy Atom Count: 29
• Complexity: 590

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1O)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)O
• Isomeric SMILES: CC1=CC(=CC(=C1O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)O

Technology Process of 2-Methyl-6-geranylgeranyl-1,4-benzoquinol

There total 4 articles about 2-Methyl-6-geranylgeranyl-1,4-benzoquinol 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: 98.0%

2,5-bis(methoxymethoxy)-1-methyl-3-<(E,E,E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>benzene (50848-62-9) → 2-methyl-6-<(E,E,E)-3,7,11,15-tetramethylhexadeca-2,6,14-tetraenyl>benzene-1,4-diol (57576-81-5)

Guidance literature:

With hydrogenchloride; In methanol; chloroform; for 1h; Heating;

DOI:10.1016/S0968-0896(01)00428-X

Reference yield:

2E,6E,10E-geranylgeranyl bromide (50848-64-1) → 2-methyl-6-<(E,E,E)-3,7,11,15-tetramethylhexadeca-2,6,14-tetraenyl>benzene-1,4-diol (57576-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: 33 percent / CuI / tetrahydrofuran / 1.5 h / -78 - 20 °C

2.1: 98 percent / conc. HCl / CHCl₃; methanol / 1 h / Heating

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/S0968-0896(01)00428-X

Reference yield:

1-bromo-2,5-bis(methoxymethoxy)-3-methylbenzene (50848-61-8) → 2-methyl-6-<(E,E,E)-3,7,11,15-tetramethylhexadeca-2,6,14-tetraenyl>benzene-1,4-diol (57576-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: 33 percent / CuI / tetrahydrofuran / 1.5 h / -78 - 20 °C

2.1: 98 percent / conc. HCl / CHCl₃; methanol / 1 h / Heating

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/S0968-0896(01)00428-X

upstream raw materials:

2,5-bis(methoxymethoxy)-1-methyl-3-<(E,E,E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>benzene

2E,6E,10E-geranylgeranyl bromide

1-bromo-2,5-bis(methoxymethoxy)-3-methylbenzene

2-bromo-6-methylbenzene-1,4-diol

Downstream raw materials:

2-(geranylgeranyl)-6-methyl-1,4-benzohydroquinone diacetate

2-methyl-6-<(E,E,E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>cyclohexa-2,5-diene-1,4-dione

delta-tocopherol