(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

• ChemBase ID: 158490
• Molecular Formular: C20H26O6
• Molecular Mass: 362.41684
• Monoisotopic Mass: 362.17293855
• SMILES: COc1cc(ccc1O)C[C@@H](CO)[C@@H](Cc1ccc(c(c1)OC)O)CO
• Canonical SMILES: OC[C@@H]([C@@H](Cc1ccc(c(c1)OC)O)CO)Cc1ccc(c(c1)OC)O
• InChI: InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
• InChIKey: PUETUDUXMCLALY-HOTGVXAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
• IUPAC Traditional name: secoisolariciresinol
• Synonyms: (2R*,3R*)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol; Secoisolariciresinol; (2R*,3R*)-2,3-双(4-羟基-3-甲氧苄基)-1,4-丁二醇; 开环异落叶松树脂酚

Database IDs

• CAS Number: 29388-59-8
• EC Number: 249-599-2
• MDL Number: MFCD01075136
• Beilstein Number: 6611290
• PubChem SID: 24881860; 162252626
• PubChem CID: 65373

CALCULATED PROPERTIES

• Acid pKa: 9.963199
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.3328462
• LogD (pH = 7.4): 2.331682
• Log P: 2.3328612
• Molar Refractivity: 99.287 cm^3
• Polarizability: 38.320282 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

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

Product Information

• Purity: ≥95.0% (HPLC); 98.0
• Grade: purum
• Empirical Formula (Hill Notation): C20H26O6

DETAILS

Sigma Aldrich - 60372

Other Notes
Component of functional food. Flaxseed lignan with antioxidant activity1
Physical form
mixture of enantiomers of the (R*,R*)-diastereoisomer