4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

• ChemBase ID: 153279
• Molecular Formular: C20H22O6
• Molecular Mass: 358.38508
• Monoisotopic Mass: 358.14163842
• SMILES: COc1cc(ccc1O)[C@@H]1[C@H]2CO[C@@H]([C@H]2CO1)c1ccc(c(c1)OC)O
• Canonical SMILES: COc1cc(ccc1O)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc(c(c1)OC)O
• InChI: InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1
• InChIKey: HGXBRUKMWQGOIE-AFHBHXEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol
• IUPAC Traditional name: pinoresinol
• Synonyms: (+)-Pinoresinol; 4,4′-((1S,3aR,4S,6aR)-Hexahydrofuro[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol); 4,4′-[(1S,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2-methoxyphenol); Pinoresinol

Database IDs

• CAS Number: 487-36-5
• MDL Number: MFCD07784516
• PubChem SID: 162247418
• PubChem CID: 73399

CALCULATED PROPERTIES

• Acid pKa: 9.609716
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.277726
• LogD (pH = 7.4): 2.2751017
• Log P: 2.2777596
• Molar Refractivity: 95.1002 cm^3
• Polarizability: 37.161057 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥6 mg/mL
• Apperance: Powder; white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC); ≥95.0% (HPLC); 98.5
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C20H22O6

DETAILS

Sigma Aldrich - 40674

Biochem/physiol Actions
Pinoresinol is present in a number of plants including medical plants like Sambucus williamsii, Eucommia ulmoides (duzhong), Styrax sp, Forsythia suspensa, and in extra virgin olive oil. The genus Sambucus is widely distributed in Europe, Asia, and North Africa, and has been used in traditional medicine as an analgesic, antivirus, antiinflammatory, homoeostatic, and diuretic drugs which act on bruises, fractures, and edema. Pinoresinol displays potent antifungal properties by causing damage to the fungal plasma membrane. It exerts anti-oxidative and anti-inflammatory activities by inhibition of TNF- α production (presumably through inhibition of NF- κB and AP-1).

Sigma Aldrich - SML0073

Biochem/physiol Actions
Pinoresinol is present in a number of plants including medical plants like Sambucus williamsii, Eucommia ulmoides (duzhong), Styrax sp, Forsythia suspensa, and in extra virgin olive oil. The genus Sambucus is widely distributed in Europe, Asia, and North Africa, and has been used in traditional medicine as an analgesic, antivirus, antiinflammatory, homoeostatic, and diuretic drugs which act on bruises, fractures, and edema. Pinoresinol displays potent antifungal properties by causing damage to the fungal plasma membrane. It exerts anti-oxidative and anti-inflammatory activities by inhibition of TNF- α production (presumably through inhibition of NF- κB and AP-1).