Ubiquinone 7

Base Information

• Chemical Name: Ubiquinone 7
• CAS No.: 303-95-7
• Molecular Formula: C44H66 O4
• Molecular Weight: 659.006
• NSC Number: 147790
• UNII: RRK47DEG6Q
• DSSTox Substance ID: DTXSID501318261
• Nikkaji Number: J1.205.855A,J11.403K
• Wikidata: Q27120651
• NCI Thesaurus Code: C87475
• Metabolomics Workbench ID: 56658
• Mol file: 303-95-7.mol

Synonyms:coenzyme Q7;CoQ7;ubiquinone 7;ubiquinone 7, (Z,Z,Z,E,E,E)-isomer

Chemical Property of Ubiquinone 7

Chemical Property:

• Melting Point: 31-32oC
• Boiling Point: 736.9oCat 760 mmHg
• Flash Point: 290.9oC
• PSA: 52.60000
• Density: 0.98 g/cm3
• LogP: 12.67440
• Storage Temp.: -20°C
• XLogP3: 13.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 22
• Exact Mass: 658.49611058
• Heavy Atom Count: 48
• Complexity: 1360

Purity/Quality:

98%min ^*data from raw suppliers

CoenzymeQ7 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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)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)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
• Uses: An isoprenoid quinone that siginificantly reduced blood sugar and ketone bodies of diabetics. It has been shown to decrease high blood citrate level in humans with periodontal disease. It is a viable therapeutic agent for muscular dystrophy.

Technology Process of Ubiquinone 7

There total 23 articles about Ubiquinone 7 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: 83.0%

trimethylaluminum (75-24-1) + 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone (202843-56-9) + (5E,9E,13E,17E,21E)-6,10,14,18,22,26-Hexamethyl-heptacosa-5,9,13,17,21,25-hexaen-1-yne (257885-58-8) → Ubichinon-7 (303-95-7)

Guidance literature:

trimethylaluminum; (5E,9E,13E,17E,21E)-6,10,14,18,22,26-Hexamethyl-heptacosa-5,9,13,17,21,25-hexaen-1-yne; With zirconocene dichloride; In hexane; 1,2-dichloro-ethane;

2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone; With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1021/ja992164p

Reference yield:

2-hydroxy-2-methyl-3-butenal dimethyl acetal (3330-23-2) → Ubichinon-7 (303-95-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: CuCl₂; NaCl; conc. aq. HCl / benzene / 5 h / 50 °C

2.1: 94 percent / NaBH₄ / tetrahydrofuran / 0.5 h / -20 °C

3.1: POCl₃

4.1: dimethylformamide / 20 °C

5.1: TsOH / methanol / 12 h / 20 °C

6.1: 65 percent / n-BuLi

7.1: 100 percent / LiBHEt₃; Pd(dppp)Cl₂ / tetrahydrofuran / 3 h / 0 °C

8.1: N-chlorosuccinimide; Me₂S / CH₂Cl₂ / 2.5 h / 0 °C

9.1: n-BuLi

9.2: -78 - 20 °C

10.1: LiBHEt₃; Pd(dppp)Cl₂ / tetrahydrofuran

11.1: TBAF / tetrahydrofuran / 1 h

12.1: Cp₂ZrCl₂ / 1,2-dichloro-ethane; hexane

12.2: 83 percent / NiCl₂(PPh₃)2; n-BuLi / tetrahydrofuran; hexane

With hydrogenchloride; sodium tetrahydroborate; N-chloro-succinimide; n-butyllithium; zirconocene dichloride; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); dimethylsulfide; tetrabutyl ammonium fluoride; lithium triethylborohydride; toluene-4-sulfonic acid; sodium chloride; copper dichloride; trichlorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene; 1.1: chlorination; rearrangement / 2.1: Reduction / 3.1: Etherification / 4.1: Substitution / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Alkylation / 7.1: desulfonylation / 8.1: Chlorination / 9.1: Metallation / 9.2: Alkylation / 10.1: desulfonylation / 11.1: desilylation / 12.1: Metallation / 12.2: Alkylation;

DOI:10.1021/ja992164p

Reference yield:

trans-3-hydroxymethyl-2-butenyl chloride (56904-88-2) → Ubichinon-7 (303-95-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: POCl₃

2.1: dimethylformamide / 20 °C

3.1: TsOH / methanol / 12 h / 20 °C

4.1: 65 percent / n-BuLi

5.1: 100 percent / LiBHEt₃; Pd(dppp)Cl₂ / tetrahydrofuran / 3 h / 0 °C

6.1: N-chlorosuccinimide; Me₂S / CH₂Cl₂ / 2.5 h / 0 °C

7.1: n-BuLi

7.2: -78 - 20 °C

8.1: LiBHEt₃; Pd(dppp)Cl₂ / tetrahydrofuran

9.1: TBAF / tetrahydrofuran / 1 h

10.1: Cp₂ZrCl₂ / 1,2-dichloro-ethane; hexane

10.2: 83 percent / NiCl₂(PPh₃)2; n-BuLi / tetrahydrofuran; hexane

With N-chloro-succinimide; n-butyllithium; zirconocene dichloride; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); dimethylsulfide; tetrabutyl ammonium fluoride; lithium triethylborohydride; toluene-4-sulfonic acid; trichlorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Alkylation / 5.1: desulfonylation / 6.1: Chlorination / 7.1: Metallation / 7.2: Alkylation / 8.1: desulfonylation / 9.1: desilylation / 10.1: Metallation / 10.2: Alkylation;

DOI:10.1021/ja992164p

upstream raw materials:

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

((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-Heptamethyl-octacosa-2,6,10,14,18,22,26-heptaenyl)-trimethyl-stannane

trimethylaluminum

2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone

Downstream raw materials:

trans-γ-Methoxy-isoubichinon-7

ubiquinol-8

ubiquinol

reduced coenzyme Q₇

Refernces

• 1、 Naruta. "Regio- and stereoselective synthesis of coenzymes Q(n) (n=2-10), vitamin K, and related polyprenylquinones". . p. 4097 - 4104. Retrieved 2007/10/02.