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Merck
CN

42914

Pinosylvin monomethyl ether

≥97.0% (HPLC)

Synonym(s):

(E)-3-Hydroxy-5-methoxystilbene, (E)-3-Methoxy-5-(2-phenylethenyl)phenol, 5-Methoxy-3-stilbenol, Pinosylvin 3-methyl ether

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About This Item

Empirical Formula (Hill Notation):
C15H14O2
CAS Number:
35302-70-6
Molecular Weight:
226.27
PubChem Substance ID:
329756282
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
1875807
MDL number:
MFCD00210546

Key Documents

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SMILES string

COc1cc(O)cc(\C=C\c2ccccc2)c1

InChI

1S/C15H14O2/c1-17-15-10-13(9-14(16)11-15)8-7-12-5-3-2-4-6-12/h2-11,16H,1H3/b8-7+

InChI key

JVIXPWIEOVZVJC-BQYQJAHWSA-N

assay

≥97.0% (HPLC)

form

solid

mp

118-122 °C

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Application

Pinosylvin, a pre-infectious stilbenoid toxin, is used to study its properties as a fungitoxin and potential therapeutic agent. Pinosylvin monomethyl ether, a methylated derivative of pinosylvin, may be used as a reference material in the analysis of stibenoid toxins. Pinosylvin monomethyl ether may also be 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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

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
BCBP6671V
BCBG3355V
BCBG3355

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Caterina Villari et al.
Tree physiology, 32(7), 867-879 (2012-06-22)
Conifer bark beetles are often associated with fungal complexes whose components have different ecological roles. Some associated species are nutritionally obligate fungi, serving as nourishment to the larvae, whereas others are pathogenic blue-stain fungi known to be involved in the
Dag Ekeberg et al.
Journal of chromatography. A, 1109(2), 267-272 (2006-02-14)
A method for quantitative determination of extractives from heartwood of Scots pine (Pinus sylvestris L.) using gas chromatography (GC) with flame ionization detection (FID) was developed. The limit of detection (LOD) was 0.03 mg/g wood and the linear range (r
C C Celimene et al.
Phytochemistry, 56(2), 161-165 (2001-02-24)
The effects of pinosylvin, pinosylvin monomethyl ether, pinosylvin dimethyl ether, and resveratrol on the fungal shoot blight and canker pathogen of conifers Sphaeropsis sapinea were examined in vitro. Effects of compounds, isolates, and concentrations on both conidial germination and mycelial
François Simard et al.
Phytotherapy research : PTR, 22(7), 919-922 (2008-04-05)
Methanol extracts of wood from Pinus resinosa were found to be selectively cytotoxic against human lung carcinoma cells, A549 (IC50 41 +/- 6 microg/mL), human colorectal adenocarcinoma cells, DLD-1 (IC50 47 +/- 4 microg/mL) in comparison with healthy cells, WS1
Julien Gabaston et al.
Journal of separation science, 43(6), 1080-1088 (2020-01-24)
Pine knots are a rich source of lignans, flavonoids, and stilbenes. These bioactive compounds are widely known for their roles to combat human disorders but also to protect plants against pathogens. In order to gain knowledge inside their potential activities
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