A stilbene with diverse biological activities
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Pinosylvin

Item No. 27612

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(1E)-2-phenylethenyl]-1,3-benzenediol
CAS Number
22139-77-1
Synonyms
  • trans-3,5-Dihydroxystilbene
Molecular Formula
C14H12O2
Formula Weight
212.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10mg/mLDMF:PBS (pH 7.2) (1:50): 0.01mg/mLDMSO: 10mg/mLEthanol: 20mg/mLEthanol:PBS (pH 7.2) (1:50): 0.01mg/mL
λmax
211, 301, 309 nm
SMILES
OC1=CC(/C=C/C2=CC=CC=C2)=CC(O)=C1
InChi Code
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
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $41

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    5 mg

    $178

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    10 mg

    $312

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    25 mg

    $631

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    Cayman Chemical
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    Product Description

    Pinosylvin is a stilbene originally isolated from pine heartwood that has diverse biological activities.1,2,3,4,5,6 It activates sirtuin 1 (SIRT1) and induces glucose uptake in isolated rat L6 skeletal muscle myotubes.2 Pinosylvin reduces radial growth in a panel of 28 plant pathogenic fungi when used at a concentration of 100 μg/ml.3 It reduces expression of matrix metalloproteinase-2 (MMP-2), MMP-9, and membrane type 1-MMP in and inhibits migration of HT-1080 cells.4 Pinosylvin (10 mg/kg, i.p.) reduces the number of tumor nodules and lung tumor weight in a CT26 mouse xenograft model of metastatic colon cancer. It decreases hind paw volume and myeloperoxidase (MPO) activity in a rat model of adjuvant-induced arthritis.5 Pinosylvin also exhibits plant antifeedant activity against L. americanus (snowshoe hares).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Alvarez-Novoa, J.C., Erdtman, H., and Lindstedt, G. Constituents of pine heartwood. XIX. The heartwood of Pinus pinea, Pinus pinaster, Pinus halepensis, and Pinus nigra. Acta Chem. Scand. 4(3), 444-447 (1950).

    2. Modi, S., Yaluri, N., Kokkola, T., et al. Plant-derived compounds strigolactone GR24 and pinosylvin activate SIRT1 and enhance glucose uptake in rat skeletal muscle cells. Sci. Rep. 7(1), 17606 (2017).

    3. Seppänen, S.K., Syrjälä, L., von Weissenberg, K., et al. Antifungal activity of stilbenes in in vitro bioassays and in transgenic Populus expressing a gene encoding pinosylvin synthase. Plant Cell. Rep. 22(8), 584-593 (2004).

    4. Park, E.-J., Park, H.-J., Chung, H.-J., et al. Antimetastatic activity of pinosylvin, a natural stilbenoid, is associated with the suppression of matrix metalloproteinases. J. Nutr. Biochem. 23(8), 946-952 (2012).

    5. Mačičková, T., Drábiková, K., Nosál', R., et al. In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis. Neuro. Endocrinol. Lett. 31(Suppl 2), 91-95 (2013).

    6. Sullivan, T.P., Crump, D.R., Wieser, H., et al. Influence of the plant antifeedant, pinosylvin, on suppression of feeding by snowshoe hares. J. Chem. Ecol. 18(7), 1151-1164 (1992).