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40674

Sigma-Aldrich

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)

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About This Item

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

Quality Level

100

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

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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.

Storage Class Code

11 - Combustible Solids

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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Frank C Schroeder et al.
Proceedings of the National Academy of Sciences of the United States of America, 103(42), 15497-15501 (2006-10-13)
Pinoresinol, a lignan of wide distribution in plants, is found to occur as a minor component in the defensive secretion produced by glandular hairs of caterpillars of the cabbage butterfly, Pieris rapae. The compound or a derivative is appropriated by
Lignans in triticale grain and triticale products
Makowska A, et al.,
Journal of Cereal Science, 93, 102939-102939 (2020)
Kishan Chandra et al.
Biotechnology reports (Amsterdam, Netherlands), 22, e00336-e00336 (2019-04-25)
Members of Cytochromes P450 super family of enzymes catalyse important biochemical reactions in plants. Some of these reactions are so important that they contribute to enormous chemical diversity seen in plants. Many unique secondary metabolites formed by mediation of these
Arin Wikul et al.
Bioorganic & medicinal chemistry letters, 22(16), 5215-5217 (2012-07-24)
Defatted sesame seeds have been reported for hypoglycemic effect in mice and T2DM women. An attempted to identify active components responsible for this effect was conducted using α-glucosidase-guided fractionation, resulting in the isolation of various lignans. Of compounds isolated, only
J L Peñalvo et al.
European journal of clinical nutrition, 66(7), 795-798 (2012-05-17)
Lignan-rich diets have been associated with favorable health effects through improved metabolic profile. In this study, we hypothesized that dietary lignan intake could be also associated with childhood obesity. We studied prevalent obesity in relation to lignan intake within the
View All Related Papers

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