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Documenti

40674

Sigma-Aldrich

Pinoresinol

≥95.0% (HPLC)

Sinonimo/i:

(+)-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

Formula empirica (notazione di Hill):
C20H22O6
Numero CAS:
487-36-5
Peso molecolare:
358.39
Numero MDL:
MFCD07784516
Codice UNSPSC:
12352205
ID PubChem:
329756010
NACRES:
NA.25

Saggio

≥95.0% (HPLC)

Forma fisica

powder or crystals

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Stringa SMILE

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
HGXBRUKMWQGOIE-AFHBHXEDSA-N

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Categorie correlate

Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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).

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Magnolin ≥95% (HPLC)

Sigma-Aldrich

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Sigma-Aldrich

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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
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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