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Merck

40674

Sigma-Aldrich

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 de CAS:
Peso molecular:
358.39
Número MDL:
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
NACRES:
NA.25

Análisis

≥95.0% (HPLC)

formulario

powder or crystals

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

cadena SMILES

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

Clave InChI

HGXBRUKMWQGOIE-AFHBHXEDSA-N

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Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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).

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Los clientes también vieron

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
Hyo Won Jung et al.
Neuroscience letters, 480(3), 215-220 (2010-07-06)
The activation of microglia plays an important role in a variety of brain disorders by the excessive production of inflammatory mediators such as nitric oxide (NO), prostaglandin E(2) (PGE(2)) and proinflammatory cytokines. We investigated here whether pinoresinol isolated from the
Yun Zhu et al.
PloS one, 12(2), e0171390-e0171390 (2017-02-06)
Mammalian lignans or enterolignans are metabolites of plant lignans, an important category of phytochemicals. Although they are known to be associated with estrogenic activity, cell signaling pathways leading to specific cell functions, and especially the differences among lignans, have not
Y Fukuhara et al.
Enzyme and microbial technology, 52(1), 38-43 (2012-12-04)
Bacterial genes for the degradation of major dilignols produced in lignifying xylem are expected to be useful tools for the structural modification of lignin in plants. For this purpose, we isolated pinZ involved in the conversion of pinoresinol from Sphingobium
Kye-Won Kim et al.
The Journal of biological chemistry, 287(41), 33957-33972 (2012-08-03)
How stereoselective monolignol-derived phenoxy radical-radical coupling reactions are differentially biochemically orchestrated in planta, whereby for example they afford (+)- and (-)-pinoresinols, respectively, is both a fascinating mechanistic and evolutionary question. In earlier work, biochemical control of (+)-pinoresinol formation had been

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