2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 76910
• Molecular Formular: C9H10O4
• Molecular Mass: 182.1733
• Monoisotopic Mass: 182.0579088
• SMILES: O=C1C(=C(C(=O)C=C1C)OC)OC
• Canonical SMILES: COC1=C(OC)C(=O)C(=CC1=O)C
• InChI: InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3
• InChIKey: UIXPTCZPFCVOQF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: coenzyme Q0
• Synonyms: 2,3-Dimethoxy-5-methyl-1,4-benzoquinone; Coenzyme Q0; 2,3-Dimethoxy-5-methyl-1,4-benzoquinone; 2,3-Dimethoxy-5-methyl-p-benzoquinone; Coenzyme Q₀; 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione; 2,3-二甲氧基-5-甲基-1,4-苯醌

Database IDs

• CAS Number: 605-94-7
• EC Number: 210-100-8
• MDL Number: MFCD00001595
• Beilstein Number: 1640422
• PubChem SID: 162041809; 24894261
• PubChem CID: 69068

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.60800374
• LogD (pH = 7.4): 0.60800374
• Log P: 0.60800374
• Molar Refractivity: 48.8231 cm^3
• Polarizability: 17.6851 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 57-60°C; 58-60 °C; 58-60 °C(lit.); 59 - 60°C
• Hydrophobicity(logP): -0.149

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Irritant; Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); 95%; 98%
• Empirical Formula (Hill Notation): C9H10O4
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02157778

(Coenzyme Q₀)

Sigma Aldrich - D9150

包装
1, 5 g in glass bottle
Application
Coenzyme Q0 inhibits (via radical quenching) reactions of gamma-irradiation induced homolytic cleavage of O-glycoside bonds in polysaccharides. Coenzyme Q0 induces apoptosis and modulates the cell cycle in estrogen receptor negative breast cancer cells. It is toxic to other cells such as insulin producing cells.

Sigma Aldrich - 38775

Other Notes
Coenzyme Q1

REFERENCES

• Reaction with tributyl(3-methyl-2-butenyl)tin in the presence of BF₃ etherate, followed by workup with FeCl₃, provides a high-yield synthesis of ubiquinone-1: Org. Synth. Coll., 9, 741 (1998):
  
• The reaction is applicable to the synthesis of a variety of polyprenylated quinones.