Coenzyme Q4

Base Information

• Chemical Name: Coenzyme Q4
• CAS No.: 4370-62-1
• Molecular Formula: C29H42 O4
• Molecular Weight: 454.65
• NSC Number: 266773
• UNII: I7G555QPVU
• DSSTox Substance ID: DTXSID901345979
• Nikkaji Number: J93.224H
• Metabolomics Workbench ID: 29078
• ChEMBL ID: CHEMBL407116
• Mol file: 4370-62-1.mol

Synonyms:COENZYME Q4;4370-62-1;Ubiquinone-4;Ubiquinone 4;Ubiquinone Q4;CoQ4;I7G555QPVU;2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]cyclohexa-2,5-diene-1,4-dione;2,3-Dimethoxy-5-methyl-6-(geranylgeranyl)-1,4-benzoquinone;NSC-266773;Ubiquinone-20;2,3-dimethoxy-5-methyl-6-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)cyclohexa-2,5-diene-1,4-dione;NSC266773;Ubidihydroquinone Q4;COENZYMEQ4;UNII-I7G555QPVU;CHEMBL407116;SCHEMBL6279406;CHEBI:149479;XGCJRRDNIMSYNC-INVBOZNNSA-N;DTXSID901345979;6-Methyl-3-(1-methylpropyl)uracil;LMPR02010003;NSC 266773;C6F752F6-69B0-4CC2-9B43-B8E7D1701247;2,3-dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-2,5-Cyclohexadiene-1,4-dione;2,3-dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-p-Benzoquinone;2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-2,5-Cyclohexadiene-1,4-dione;2,5-CYCLOHEXADIENE-1,4-DIONE, 2,3-DIMETHOXY-5-METHYL-6-((2E,6E,10E)-3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAEN-1-YL)-;p-Benzoquinone, 2,3-dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-

Chemical Property of Coenzyme Q4

Chemical Property:

• Vapor Pressure: 1.05E-12mmHg at 25°C
• Boiling Point: 584.1°Cat760mmHg
• Flash Point: 244.8°C
• PSA: 52.60000
• Density: 1.01g/cm³
• LogP: 7.49490
• Storage Temp.: −20°C
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 454.30830982
• Heavy Atom Count: 33
• Complexity: 900

Purity/Quality:

99% ^*data from raw suppliers

Coenzyme Q4 ≥90% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
• Isomeric SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
• Uses: Coenzyme Q4 (CoQ4) is a 4 isoprenyl group member of a family of ubiquinones that share a quinine chemical group but differ in the number of isoprenyl chemical subunits in their tail. The CoQ compounds are lipid soluble components of cell membranes where they perform multiple functions such as electron and proton transport. The most well studied CoQ compound is CoQ10. CoQ4 is frequently used in comparison studies on the effect of isoprenyl chain length on CoQ functions or distribution.

Technology Process of Coenzyme Q4

There total 12 articles about Coenzyme Q4 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: 81.1%

trimethylaluminum (75-24-1) + (5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-yne (22842-11-1,80713-11-7,140677-79-8) + 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone (202843-56-9) → 2-<(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>-3-methyl-5,6-dimethoxy-1,4-benzoquinone (4370-62-1)

Guidance literature:

trimethylaluminum; (5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-yne; With methylalumoxane; rac-ethylenebis(1-indenyl)zirconium(IV) chloride; In toluene; at 20 ℃; for 8h;

2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone; bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; In tetrahydrofuran; at -20 ℃; for 2h;

DOI:10.1021/ja065769b

Reference yield: 78.0%

1-<(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>-6-methyl-2,3,4,5-tetramethoxybenzene (114060-26-3) → 2-<(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>-3-methyl-5,6-dimethoxy-1,4-benzoquinone (4370-62-1)

Guidance literature:

With ceric ammoniumnitrate; In dichloromethane; water; acetonitrile;

DOI:10.1021/ja00221a040

Reference yield:

3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene (53254-60-7) → 2-<(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>-3-methyl-5,6-dimethoxy-1,4-benzoquinone (4370-62-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / potassium tert-butoxide / dimethylformamide / -20 deg C, 2 h then room temp., 1 h

2: 84 percent / Pd(PPh₃)4; diethylaniline, pyridine / tetrahydrofuran / 4 h

3: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C

4: 92 percent / Pd(dppp)Cl₂, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C

5: 78 percent / ceric ammoniumnitrate / acetonitrile; H₂O; CH₂Cl₂

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); ceric ammoniumnitrate; potassium tert-butylate; lithium triethylborohydride; caesium carbonate; N,N-diethylaniline; 4-aminotiophenol; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00221a040

upstream raw materials:

2,3-Dimethoxy-5-methyl-1,4-benzoquinone

Trimethyl-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-stannane

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

trimethylaluminum

Downstream raw materials:

ubiquinol-4

Refernces

• 1、 Eren, Doron,Keinan, Ehud. "Total Synthesis of Linear Polyprenoids. 3. Syntheses of Ubiquinones via Palladium-Catalyzed Oligomerization of Monoterpene Monomers". . p. 4356 - 4362. Retrieved 2007/10/02.