methyl 4-[5-(hydroxymethyl)-7-methoxy-2H-1,3-benzodioxol-4-yl]-7-methoxy-2H-1,3-benzodioxole-5-carboxylate

• ChemBase ID: 154477
• Molecular Formular: C19H18O9
• Molecular Mass: 390.34082
• Monoisotopic Mass: 390.09508216
• SMILES: COc1cc(c(c2c1OCO2)c1c(cc(c2c1OCO2)OC)C(=O)OC)CO
• Canonical SMILES: COC(=O)c1cc(OC)c2c(c1c1c(CO)cc(c3c1OCO3)OC)OCO2
• InChI: InChI=1S/C19H18O9/c1-22-11-4-9(6-20)13(17-15(11)25-7-27-17)14-10(19(21)24-3)5-12(23-2)16-18(14)28-8-26-16/h4-5,20H,6-8H2,1-3H3
• InChIKey: KXMTXZACPVCDMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-[5-(hydroxymethyl)-7-methoxy-2H-1,3-benzodioxol-4-yl]-7-methoxy-2H-1,3-benzodioxole-5-carboxylate
• IUPAC Traditional name: methyl 4-[5-(hydroxymethyl)-7-methoxy-2H-1,3-benzodioxol-4-yl]-7-methoxy-2H-1,3-benzodioxole-5-carboxylate
• Synonyms: 4, 4′-dimethoxy-2, 3, 2′, 3′-bis(methylenedioxy)-6-hydroxymethyl-6′-methoxy-carbonyl biphenyl; Bicyclol

Database IDs

• CAS Number: 118159-48-1
• MDL Number: MFCD00889471
• PubChem SID: 162248616
• PubChem CID: 9821754

CALCULATED PROPERTIES

• Acid pKa: 15.0281725
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.7877228
• LogD (pH = 7.4): 1.7877228
• Log P: 1.7877228
• Molar Refractivity: 94.4956 cm^3
• Polarizability: 38.218 Å^3
• Polar Surface Area: 101.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• RTECS: DT4312000
• European Hazard Symbols: Nature polluting (N)
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H18O9

DETAILS

Sigma Aldrich - B3313

Biochem/physiol Actions
Bicyclol is a anti-hepatitis drug, used in China for chronic hepatitis B and presumably C. The drug appears to protect against liver injury in animals. Recently it was reported that bicyclol induce the expression of hepatic HSP27 and HSP70, and thus consequently inhibits the transcription factor NF-?B-mediated apoptosis and necrosis in liver tissue. It appears that bicyclol induces hepatic HSP27 and HSP70 expression through activating transcription of HSPs genes.