5,6-dimethoxy-2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohex-2-ene-1,4-dione

• ChemBase ID: 133766
• Molecular Formular: C29H44O4
• Molecular Mass: 456.65726
• Monoisotopic Mass: 456.32395989
• 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
• Canonical SMILES: COC1C(OC)C(=O)C(=C(C1=O)C/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C)C
• InChI: InChI=1S/C29H44O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-23(5)18-19-25-24(6)26(30)28(32-7)29(33-8)27(25)31/h12,14,16,18,28-29H,9-11,13,15,17,19H2,1-8H3/b21-14+,22-16+,23-18+
• InChIKey: MDLQEORKYVBTDV-INVBOZNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,6-dimethoxy-2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohex-2-ene-1,4-dione
• IUPAC Traditional name: 5,6-dimethoxy-2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohex-2-ene-1,4-dione
• Synonyms: 2,3-Dimethoxy-5-methyl-6-(geranylgeranyl)-1,4-benzoquinone; Q-4; Ubiquinone-20; Ubiquinone-4; Coenzyme Q4

Database IDs

• CAS Number: 4370-62-1
• MDL Number: MFCD00077923
• Beilstein Number: 2066531
• PubChem SID: 162228043; 24892492
• PubChem CID: 16219098

CALCULATED PROPERTIES

• Acid pKa: 17.099367
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 7.5078707
• LogD (pH = 7.4): 7.5078707
• Log P: 7.5078707
• Molar Refractivity: 141.4612 cm^3
• Polarizability: 53.753494 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%

DETAILS

Sigma Aldrich - C2470

Application
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.
Biochem/physiol Actions
Increases the fluorescence polarization of perylene incorporated into ubiquinone-depleted mitochondrial and bilayer vesicles prepared from mitochondrial phospholipids
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C2470.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.