(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

• ChemBase ID: 3813
• Molecular Formular: C20H22O6
• Molecular Mass: 358.38508
• Monoisotopic Mass: 358.14163842
• SMILES: c1c(c(ccc1C[C@H]1COC(=O)[C@@H]1Cc1ccc(c(c1)OC)O)O)OC
• Canonical SMILES: COc1cc(ccc1O)C[C@H]1C(=O)OC[C@@H]1Cc1ccc(c(c1)OC)O
• InChI: InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1
• InChIKey: MATGKVZWFZHCLI-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• IUPAC Traditional name: matairesinol
• Synonyms: Artigenin congener; (-)-Matairesinol; Dibenzylbutyrolactone lignanolide; (alphaR,betaR)-alpha,beta-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone; 3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone; Matairesinol; (αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone; Matairesinol; (αR,βR)-α,β-双(4-羟基-3-甲氧苯基)丁内酯; 罗汉松脂酚

Database IDs

• CAS Number: 580-72-3
• MDL Number: MFCD03453216
• Beilstein Number: 7826317
• PubChem SID: 46507098; 24864917; 160967250
• PubChem CID: 119205
• CHEMBL: 425148
• Chemspider ID: 106491
• DrugBank ID: DB04200
• Wikipedia Title: Matairesinol

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.644701
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.2917516
• LogD (pH = 7.4): 3.28933
• Log P: 3.2917826
• Molar Refractivity: 95.6344 cm^3
• Polarizability: 37.27576 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.79
• LOG S: -4.47
• Solubility (Water): 1.21e-02 g/l

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥85% (HPLC); 98.5
• Empirical Formula (Hill Notation): C20H22O6

DETAILS

DrugBank - DB04200

Drug information: experimental

Sigma Aldrich - 40043

Other Notes
Matairesinol, a phytoestrogen is employed as dietary supplement leading to metabolites with estrogenic properties1; HPLC determination of matairesinol2