A stilbene with diverse biological activities
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Tapinarof

Item No. 36527

Technical Information
Formal Name
2-(1-methylethyl)-5-[(1E)-2-phenylethenyl]-1,3-benzenediol
CAS Number
79338-84-4
Synonyms
  • Benvitimod
  • WBI-1001
Molecular Formula
C17H18O2
Formula Weight
Purity
≥98%
A solid
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/ml
λmax
211, 240, 318 nm
SMILES
OC(C=C1/C=C/C2=CC=CC=C2)=C(C(O)=C1)C(C)C
InChi Code
InChI=1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
InChi Key
ZISJNXNHJRQYJO-CMDGGOBGSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tapinarof is a stilbene that has been found in P. luminescens and has diverse biological activities.1,2 It is active against the fungi C. tropicales, C. neoformans, and A. fumigatus (MICs = 25, 12, and 12 µg/ml, respectively) and the plant pathogenic fungi A. flavus and B. cinerea (MICs = 25 and 12 µg/ml, respectively).1 It induces nuclear translocation of the aryl hydrocarbon receptor (AhR; EC50 = 0.16 nM) and expression of the AhR target gene CYP1A1 in HaCaT keratinocytes when used at a concentration of 1 µM.2 Tapinarof (10 µM) reduces activated immune cell-induced mRNA expression of the gene encoding IL-17a in isolated human keratinocytes.2,3 Formulations containing tapinarof have been used in the topical treatment of adult plaque psoriasis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, J., Chen, G., Wu, H., et alIdentification of two pigments and a hydroxystilbene antibiotic from Photorhabdus luminescens. Appl. Environ. Microbiol. 61(12), 4329-4333 (1995).

    2. Smith, S.H., Jayawickreme, C., Rickard, D.J., et alTapinarof is a natural AhR agonist that resolves skin inflammation in mice and humans. J. Invest. Dermatol. 137(10), 2110-2119 (2017).

    3. Smith, S.H., Peredo, C.E., Takedo, Y., et alDevelopment of a topical treatment for psoriasis targeting RORγ: From bench to skin. PLoS One 11(2), e0147979 (2016).