06892

(+)-Lariciresinol

≥95.0% (HPLC)

• Synonym(s): (2S,3R,4R)-Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-furanmethanol, 4-[(2S,3R,4R)-4-[(4-Hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol, NSC 329247
• Empirical Formula (Hill Notation): C₂₀H₂₄O₆
• CAS Number: 27003-73-2
• Molecular Weight: 360.40
• NACRES: NA.25
• PubChem Substance ID: 329748296
• UNSPSC Code: 12352005
• MDL number: MFCD07784476
• Beilstein/REAXYS Number: 4560057

Properties

• Quality Segment: 100
• assay: ≥95.0% (HPLC)
• form: powder
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• SMILES string: COc1cc(C[C@H]2CO[C@@H]([C@H]2CO)c3ccc(O)c(OC)c3)ccc1O
• InChI: 1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
• InChI key: MHXCIKYXNYCMHY-AUSJPIAWSA-N

Description

General description

Lariciresinol(LA) is a dietary phytoestrogen plant lignan. It is one of the main active phytochemicals in many traditional medicinal plants and cereals.

Application

Lariciresinol has been used as a reference standard:

• in the purification, identification, and analysis of lignan phytoestrogens and lignan glycosides
• for the determination of the enantiomeric composition of lariciresinol from the pinoresinol to lariciresinol reduction reaction using high-performance liquid chromatography (HPLC)
• forqualitative and quantitative analysis of lignans in seven types of triticalegrain using ultra-performance liquid chromatography (UPLC)

Biochem/physiol Actions

Lariciresinol is a potent dietary antioxidant and a radical scavenger by potentially chelating catalytic Fe²⁺ ions. It exerts antimicrobial effects against foodborne pathogens S. aureus and E. coli O157:H7. Lariciresinol is an effective anticancer agent that inhibits cell proliferation and induces apoptosis in human HepG2 cells in vitro. It also displays anti-inflammatory and anti-diabetic effects in vitro and in vivo studies respectively.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• pictograms: GHS09
• signalword: Warning
• hcodes: H400
• pcodes: P273 - P391 - P501
• Hazard Classifications: Aquatic Acute 1
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable