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06709

Pinoresinol

analytical standard

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
NACRES:
NA.24
PubChem Substance ID:
329748263
UNSPSC Code:
85151701
MDL number:
MFCD07784516
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Quality Level

100

grade

analytical standard

assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

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

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Wen-Jie Li et al.
Molecules (Basel, Switzerland), 17(8), 8773-8781 (2012-07-27)
Two new compounds, (2S,3R)-methyl 7-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylate (1) and (4R,5S)-5-(3-hydroxy-2,6-dimethylphenyl)-4-isopropyldihydrofuran-2-one (2), tentatively named norcurlignan and limlactone, respectively, were isolated from Liriope muscari, together with the known compound (-)-pinoresinol (3). The structures of these compounds were elucidated and characterized on the basis of
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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