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Merck

40674

Pinoresinol

≥95.0% (HPLC)

Sinónimos:

(+)-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

Fórmula empírica (notación de Hill):
C20H22O6
Número CAS:
Peso molecular:
358.39
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:

Nombre del producto

Pinoresinol, ≥95.0% (HPLC)

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

SMILES string

COc1cc(ccc1O)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c4ccc(O)c(OC)c4

InChI key

HGXBRUKMWQGOIE-AFHBHXEDSA-N

assay

≥95.0% (HPLC)

form

powder or crystals

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

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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).
exerts anti-oxidative and anti-inflammatory activities by inhibition of TNF-α production

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
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)
Hyo-Yeon Kim et al.
Journal of pharmacological sciences, 112(1), 105-112 (2010-01-23)
Forsythiae Fructus is known to have diuretic, anti-bacterial, and anti-inflammatory activities. This study examined the hepatoprotective effects of pinoresinol, a lignan isolated from Forsythiae Fructus, against carbon tetrachloride (CCl(4))-induced liver injury. Mice were treated intraperitoneally with vehicle or pinoresinol (25
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

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