Ubiquinone-1

Base Information

• Chemical Name: Ubiquinone-1
• CAS No.: 727-81-1
• Molecular Formula: C14H18 O4
• Molecular Weight: 250.295
• NSC Number: 268269
• UNII: JR17826E4G
• DSSTox Substance ID: DTXSID10223001
• Nikkaji Number: J93.220E
• Wikipedia: Coenzyme_Q5
• Wikidata: Q27097877
• Metabolomics Workbench ID: 37971
• ChEMBL ID: CHEMBL1236594
• Mol file: 727-81-1.mol

Synonyms:coenzyme Q1;coenzyme Q5;CoQ1;ubiquinone 5;Ubiquinone Q1

Chemical Property of Ubiquinone-1

Chemical Property:

• Vapor Pressure: 2.92E-06mmHg at 25°C
• Boiling Point: 389.1°C at 760 mmHg
• Flash Point: 172°C
• PSA: 52.60000
• Density: 1.1g/cm³
• LogP: 2.31540
• Storage Temp.: −20°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 250.12050905
• Heavy Atom Count: 18
• Complexity: 474

Purity/Quality:

98%,99%, ^*data from raw suppliers

Coenzyme Q1 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)CC=C(C)C
• Description: Cooenzyme Q10 (CoQ10) is a component of the electron transport chain and participates in aerobic cellular respiration, generating energy in the form of ATP. CoQ1 is an amphipathic CoQ10 homolog that has a tail consisting of five isoprene units. It has been used as an electron acceptor to study a range of oxidoreductases as isolated enzymes, in subcellular fractions, in intact cells in culture, and in perfused organs. Ubiquinone analogs, including CoQ1, impact mitochondrial permeability transition pore (PTP) formation, as well as PTP-dependent cell death, in an analog- and cell-specific manner.
• Uses: Coenzyme Q1 has been used to measure the mitochondrial respiratory chain complex 1 activity. Coenzyme Q1 is an electron acceptor and a component of the electron transport chain. It also play a role in the?mitochondrial permeability transition pore (PTP). Coenzyme Q1 is structurally similar to?coenzyme Q2 (C636450)?and?coenzyme Q10 (C636501).

Technology Process of Ubiquinone-1

There total 17 articles about Ubiquinone-1 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: 70.0%

2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) + prenyl bromide (870-63-3) → 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone (727-81-1)

Guidance literature:

2,3-Dimethoxy-5-methyl-1,4-benzoquinone; prenyl bromide; With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; In dichloromethane; for 0.5h; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1177/1747519819876524

Reference yield: 41.0%

2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) → 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone (727-81-1)

Guidance literature:

In benzene; at 100 ℃; for 2h; Irradiation;

DOI:10.1246/cl.2000.1234

Reference yield: 41.0%

2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) + p-methylphenyl prenyl telluride (316801-22-6) → 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone (727-81-1)

Guidance literature:

In benzene; at 100 ℃; for 2h; Photolysis;

DOI:10.1016/S0040-4020(02)00784-6

upstream raw materials:

1-ubiquinol

2,3-dimethoxy-5-methylbenzene-1,4-diol

3-methyl-2-buten-1-ol

1-bromo-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene

Downstream raw materials:

1-ubiquinol

1,4-bis(benzyloxy)-2,3-dimethoxy-5-methyl-6-(3-methylbut-2-enyl)benzene

1,4-bis(benzyloxy)-2-{(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-5-[(4-methylphenyl)sulfonyl]tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl}-5,6-dimethoxy-3-methylbenzene

(2E)-4-[2,5-bis(benzyloxy)-3,4-dimethoxy-6-methylphenyl]-2-methylbut-2-en-1-ol

Refernces

• 1、 Bovicelli, Paolo,Borioni, Giorgio,Fabbrini, Danilo,Barontini, Maurizio. "New efficient synthesis of ubiquinones". . p. 391 - 400. Retrieved 2008/04/01.
• 2、 Lu, Liang,Chen, Fener. "A novel and convenient synthesis of coenzyme Q1". . p. 4049 - 4053. Retrieved 2007/10/03.