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06892

Sigma-Aldrich

(+)-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

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About This Item

Empirical Formula (Hill Notation):
C20H24O6
CAS Number:
27003-73-2
Molecular Weight:
360.40
Beilstein:
4560057
MDL number:
MFCD07784476
UNSPSC Code:
12352005
PubChem Substance ID:
329748296
NACRES:
NA.25

Quality Level

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

Related Categories

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.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hisashi Nishiwaki et al.
Journal of agricultural and food chemistry, 59(24), 13089-13095 (2011-11-10)
All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S(N)1 or S(N)2 intramolecular etherification. 8- and 8'-position configurations were established from the starting material except for all
Simone Angeloni et al.
Journal of mass spectrometry : JMS, 53(9), 842-848 (2018-06-21)
Lignans are polyphenolic compounds that are considered phytoestrogens for their plant origins, and they possess different biological activities. Three different extraction methods, ie, "dilute and shoot", acidic hydrolysis, and enzymatic digestion, have been compared for extracting lignans (secoisolariciresinol (SECO), matairesinol
Bomi Hwang et al.
Biochemical and biophysical research communications, 410(3), 489-493 (2011-06-18)
Lariciresinol is an enterolignan precursor isolated from the herb Sambucus williamsii, a folk medicinal plant used for its therapeutic properties. In this study, the antifungal properties and mode of action of lariciresinol were investigated. Lariciresinol displays potent antifungal properties against
Niina M Saarinen et al.
International journal of cancer, 123(5), 1196-1204 (2008-06-06)
Lariciresinol is a dietary lignan that accounts for a significant portion of the total phytoestrogen intake from Western foods. Recent epidemiological studies suggest that high dietary intake of lignans and lariciresinol is associated with reduced breast cancer risk. However, no
Heidi Schwartz et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 838(2), 78-85 (2006-06-06)
The paper describes a method for the determination of selected lignans in plant foods. First, samples were submitted to methanolysis resulting in cleavage of ester bonds between lignan glycosides and organic acids. Glycosidic linkages were then broken by enzymatic hydrolysis
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