Chemistry:Benvitimod

Benvitimod

Names
Preferred IUPAC name 5-[(E)-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1,3-diol
Other names (E)-3,5-Dihydroxy-4-isopropyl-trans-stilbene 3,5-Dihydroxy-4-isopropylstilbene
Identifiers
CAS Number	79338-84-4 Y
3D model (JSmol)	Interactive image
ChemSpider	4943924
PubChem CID	6439522
UNII	84HW7D0V04 Y
InChI 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+ Key: ZISJNXNHJRQYJO-CMDGGOBGSA-N
SMILES CC(C)c1c(cc(cc1O)/C=C/c2ccccc2)O
Properties
Chemical formula	C17H18O2
Molar mass	254.329 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tracking categories (test):

• SizeSet

Benvitimod (also known as tapinarof or 3,5-dihydroxy-4-isopropyl-trans-stilbene) is a bacterial stilbenoid produced in Photorhabdus bacterial symbionts of Heterorhabditis nematodes. It is a product of an alternative ketosynthase-directed stilbenoid biosynthesis pathway. It is derived from the condensation of two β-ketoacyl thioesters. It is produced by the Photorhabdus luminescens bacterial symbiont species of the entomopathogenic nematode, Heterorhabditis megidis. Experiments with infected larvae of Galleria mellonella, the wax moth, support the hypothesis that the compound has antibiotic properties that help minimize competition from other microorganisms and prevents the putrefaction of the nematode-infected insect cadaver.

Entomopathogenic nematodes emerging from a wax moth cadaver

Medical research

Benvitimod is being studied in clinical trials for the treatment of plaque psoriasis.

See also

• Pinosylvin, a molecule produced in pines that does not bear the isopropyl alkylation.