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SML0073

Sigma-Aldrich

Pinoresinol

≥95% (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:
12352200
PubChem Substance ID:
329825136

Assay

≥95% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥6 mg/mL

shipped in

wet ice

storage temp.

−20°C

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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Application

Pinoresinol may be used in cell signaling studies.

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

Features and Benefits

This compound is featured on the Cytokine Receptors (Tumor Necrosis Receptor Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
044M4766V
063M4732V
102M4733V
052M4725V
071M4720V

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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
Yun-Fang Li et al.
Journal of Asian natural products research, 15(9), 934-940 (2013-08-16)
Three new 7,8-secolignans, schisandlignans A-C (1, 2, and 4), one new dibenzocyclooctadiene lignan, schisandlignan D (5), together with nine known lignans 3',4'-dimethoxybenzoic acid (3″,4″-dimethoxyphenyl)-2-methyl-3-oxobutyl ester (3), gomisin J (6), rubrisandrin A(1b) (7), interiotherin B (8), schisantherin D (9), ( - )-machilusin (10)
An enantiocomplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols.
Benjamin Pickel et al.
Angewandte Chemie (International ed. in English), 49(1), 202-204 (2009-12-01)
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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