40674

Pinoresinol

≥95.0% (HPLC)

• Synonym(s): (+)-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)
• Empirical Formula (Hill Notation): C₂₀H₂₂O₆
• CAS Number: 487-36-5
• Molecular Weight: 358.39
• MDL number: MFCD07784516
• UNSPSC Code: 12352205
• PubChem Substance ID: 329756010
• NACRES: NA.25

Properties

• assay: ≥95.0% (HPLC)
• form: powder or crystals
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• SMILES string: COc1cc(ccc1O)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c4ccc(O)c(OC)c4
• 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
• InChI key: HGXBRUKMWQGOIE-AFHBHXEDSA-N

Description

General description

Pinoresinol is a secondary metabolite, a lignan found in wide varieties of plants. Structurally, it is one of the simple lignans, with a dimer of coniferyl alcohol, which forms the bicyclic ring core.

Application

Pinoresinol has been used:

• as a reference standard for qualitative and quantitative analysis of lignans from Triticale (X Triticosecale Wittmack) grains using ultra-performance liquid chromatography (UPLC) with photodiode and mass TQD detectors
• as an enterolignan precursor to study its estrogenic activity on the proliferation of human breast cancer MCF-7 cells
• as a reference standard for lignan analysis of Sesamum indicum L. seeds

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).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable