727-81-1

Basic information

• Product Name: COENZYME Q1
• Synonyms: 2,3-DIMETHOXY-5-METHYL-6-(3-METHYL-2-BUTENYL)-1,4-BENZOQUINONE;COENZYME Q1;UBIQUINONE-5;2,3-dimethoxy-5-methyl-6-(3-methylbut-2-enyl)cyclohexa-2,5-diene-1,4-dione;Ubiquinone Q1;2,3-Dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone, Ubiquinone-1, Ubiquinone-5;2,3-Dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-2,5-cyclohexadiene-1,4-dione;2-Isopentenyl-5,6-dimethoxy-3-methyl-p-benzoquinone
• CAS NO: 727-81-1
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29
• Mol File: 727-81-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 389.1°C at 760 mmHg
• Flash Point: 172°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 2.92E-06mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: −20°C
• CAS DataBase Reference: COENZYME Q1(CAS DataBase Reference)
• NIST Chemistry Reference: COENZYME Q1(727-81-1)
• EPA Substance Registry System: COENZYME Q1(727-81-1)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 727-81-1(Hazardous Substances Data)

Usage

Description

Coenzyme Q1 (CoQ1) is an amphipathic CoQ10 homolog that plays a crucial role in the electron transport chain, participating in aerobic cellular respiration and generating energy in the form of ATP. It has a tail consisting of five isoprene units and has been used as an electron acceptor to study a range of oxidoreductases in various biological systems. CoQ1 also impacts mitochondrial permeability transition pore (PTP) formation and PTP-dependent cell death in an analogand cell-specific manner.

Uses

Used in Mitochondrial Respiratory Chain Complex 1 Activity Measurement:
Coenzyme Q1 is used as a tool to measure the activity of the mitochondrial respiratory chain complex 1, which is essential for understanding cellular respiration and energy production.
Used in Electron Transport Chain and Oxidoreductase Studies:
Coenzyme Q1 serves as an electron acceptor and a component of the electron transport chain, playing a vital role in aerobic cellular respiration. It is also used to study a range of oxidoreductases in isolated enzymes, subcellular fractions, intact cells in culture, and perfused organs.
Used in Mitochondrial Permeability Transition Pore (PTP) Research:
Coenzyme Q1 impacts the formation of mitochondrial permeability transition pore (PTP) and PTP-dependent cell death in an analogand cell-specific manner, making it a valuable compound for researching mitochondrial function and cell death mechanisms.
Used in Structural Comparisons with Other Coenzyme Q Analogs:
Due to its structural similarity to coenzyme Q2 (C636450) and coenzyme Q10 (C636501), Coenzyme Q1 is used for comparative studies to understand the differences and similarities between these CoQ analogs and their roles in cellular processes.

Biochem/physiol Actions

Coenzyme Q1 (CoQ1) is a 1 isoprenyl group (not naturally occurring) 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. CoQ1 is frequently used in comparison studies on the effect of isoprenyl chain length on CoQ functions or distribution and to identify quinone reductases.

InChI:InChI=1/C14H18O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6H,7H2,1-5H3

Upstream product

• 52590-98-4 1-ubiquinol 
• 3066-90-8 2,3-dimethoxy-5-methylbenzene-1,4-diol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 34407-31-3 1-bromo-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 870-63-3 prenyl bromide 
• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 316801-22-6 p-methylphenyl prenyl telluride 
• 808758-65-8 2-(3-methyl-2-butenyl)-4,5-dimethoxy-7-methyltricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione 
• 84551-68-8 1-methyl ether of 2,3-dimethoxy-5-methyl-6-prenylhydroquinone 
• 6443-69-2 3,4,5-trimethoxytoluene 
• 22383-85-3 2,3,4-trimethoxy-6-methylbenzaldehyde 
• 152984-32-2 4,5-dimethoxy-2-methyltricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 34417-79-3 2-bromo-5,6-dimethoxy-3-methylbenzene-1,4-diol 

Downstream Products

• 52590-98-4 1-ubiquinol 
• 911125-73-0 (E)-4-(2,5-Bis-benzyloxy-3,4-dimethoxy-6-methyl-phenyl)-2-methyl-but-2-enal 
• 303-98-0 ubidecarenone 
• 66958-69-8 1,4-bis(benzyloxy)-2-[(2E)-4-bromo-3-methylbut-2-enyl]-5,6-dimethoxy-3-methylbenzene 
• 70238-42-5 (2E)-4-[2,5-bis(benzyloxy)-3,4-dimethoxy-6-methylphenyl]-2-methylbut-2-en-1-ol 
• 70854-63-6 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 
• 66958-67-6 1,4-bis(benzyloxy)-2,3-dimethoxy-5-methyl-6-(3-methylbut-2-enyl)benzene 

Relevant articles and documents

A convenient two-step synthesis of Coenzyme Q1

A convenient method for the preparation of Coenzyme Q1 from cheap and readily available 3,4,5-trimethoxytoluene is developed. Coenzyme Q1 is synthesized in a moderate yield by a two-step procedure involving the key reaction of an allyl bromide with Coenzyme Q0 through a redox chain reaction. The reaction is efficient and can be used for the synthesis of other Coenzyme Q compounds.

Radical-scavenging polyphenols: New strategies for their synthesis

New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxytyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.

A new synthetic route to substituted quinones by radical-mediated coupling of organotellurium compounds with quinones

Carbon-centered radicals generated from the corresponding organotellurium compounds react with a variety of quinones under photo-thermal conditions to give the monoaddition product in moderate to excellent yield. The reaction can be used for the synthesis of polyprenyl quinoid natural products and C-glycosides.