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56297

Sigma-Aldrich

Pinosylvin

≥97.0% (HPLC)

Synonym(s):

(E)-3,5-Stilbenediol, (E)-5-(2-Phenylethenyl)-1,3-benzenediol, 5-Styrylresorcinol, trans-3,5-Dihydroxystilbene, Pinosylvine

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About This Item

Empirical Formula (Hill Notation):
C14H12O2
CAS Number:
22139-77-1
Molecular Weight:
212.24
Beilstein/REAXYS Number:
1870942
MDL number:
MFCD00210544
UNSPSC Code:
41116107
PubChem Substance ID:
329758200
NACRES:
NA.25

assay

≥97.0% (HPLC)

form

solid

storage condition

protect from light

mp

153-157 °C

shipped in

wet ice

storage temp.

2-8°C

SMILES string

Oc1cc(O)cc(\C=C\c2ccccc2)c1

InChI

1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+

InChI key

YCVPRTHEGLPYPB-VOTSOKGWSA-N

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Application

Pinosylvin, a pre-infectious stilbenoid toxin, is used to study its properties as a fungitoxin and therapeutic agent. Pinosylvin is used as a representative stilbene to study its biological actions and therapeutic value in processes such as cell survival, apoptosis and cell mobility.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

sensitive to oxidation

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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José Manuel López-Nicolás et al.
Journal of agricultural and food chemistry, 57(21), 10175-10180 (2009-10-10)
The complexation of pinosylvin, a potent antimicrobial and antifungal stilbenoid, by cyclodextrins (CDs) is described for first time in this work. Steady-state fluorescence was used to demonstrate that natural (alpha-, beta-, and gamma-CD) and modified (HP-beta-CD, methyl-beta-CD, and ethyl-beta-CD) CDs
Eun-Jung Park et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 55, 424-433 (2013-01-22)
Pinosylvin, a naturally occurring trans-stilbenoid mainly found in Pinus species, has exhibited a potential cancer chemopreventive activity. However, the growth inhibitory activity against cancer cells and the underlying molecular mechanisms remain to be elucidated. Therefore, the anti-proliferative activity of pinosylvin
Mirka Laavola et al.
Molecules (Basel, Switzerland), 24(1) (2019-01-02)
Interleukin-6 (IL-6) is involved in the pathogenesis of various inflammatory diseases, like rheumatoid arthritis (RA). In the present study, we investigated the role of IL-6 in osteoarthritis (OA) patients and the effects of the stilbenoids monomethyl pinosylvin and pinosylvin on
Eunsil Jeong et al.
Phytotherapy research : PTR, 27(4), 610-617 (2012-06-28)
Pinosylvin is a phenolic compound mainly found in the Pinus species. To determine the vascular functions of pinosylvin, we first examined both proliferation and apoptosis of bovine aortic endothelial cells (BAECs) in the presence of pinosylvin. When BAECs were treated
Andrea Ganthaler et al.
Plant molecular biology, 94(3), 229-251 (2017-02-13)
Accumulation of phenolic needle metabolites in Norway spruce is regulated by many genes with small and additive effects and is correlated with the susceptibility against fungal attack. Norway spruce accumulates high foliar concentrations of secondary phenolic metabolites, with important functions
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