Name | 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol |
Synonyms | WB-1001 Tapinarof GSK2894512) Tapinarof (WBI 1001 3,5-Dihydroxy-4-isopropylstilbene 3,5-Dihydroxy-4-isopropyl-trans-stilbene 5-[(E)-2-phenylethenyl]-2-(propan-2-yl)benzene-1,3-diol (E)-2-(1-Methylethyl)-5-(2-phenylethenyl)-1,3-benzenediol 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol 1,3-benzenediol, 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]- 1,3-Benzenediol, 2-(1-methylethyl)-5-(2-phenylethenyl)-, (E)- |
CAS | 79338-84-4 |
EINECS | 1312995-182-4 |
InChI | InChI=1/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+ |
Molecular Formula | C17H18O2 |
Molar Mass | 254.32 |
Density | 1.158 |
Melting Point | 140 - 142°C |
Boling Point | 431.8±20.0 °C(Predicted) |
Flash Point | 204.2°C |
Solubility | Chloroform (Slightly), Methanol (Slightly) |
Vapor Presure | 4.62E-08mmHg at 25°C |
Appearance | Solid |
Color | Pale Brown to Light Brown |
pKa | 9.86±0.15(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.665 |
In vitro study | Tapinarof activates the AhR pathway through direct binding. Tapinarof dose-dependently induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) (EC 50 =0.16 nM). |
In vivo study | Tapinarof acts through AhR to reduce inflammation in IMQ-treated mice. AhR-sufficient mice on a C57Bl/6 background exhibit a reduced clinical score after treatment with Tapinarof or 6-formylindolo(3,2-b)carbazole (FICZ). In contrast, AhR KO mice do not respond to the anti-inflammatory effects of Tapinarof. FICZ is used as a comparator in these studies and yields similar results, with dramatically reduced inflammatory responses in wild-type, but not AhR KO mice. |