3,5-Dihydroxy-4-isopropyl-''trans''-stilbene

3,5-Dihydroxy-4-isopropyl-trans-stilbene
Names

IUPAC name 5-(2-Phenylethenyl)-2-propan-2-ylbenzene-1,3-diol
Other names (E)-3,5-Dihydroxy-4-isopropyl-trans-stilbene 3,5-Dihydroxy-4-isopropylstilbene
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	4943924
PubChem CID	6439522
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	254.33 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

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 stibenoids biosynthesis pathway. It is derived from the condensation of two β-ketoacyl thioesters .^[1] 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.^[2]

Entomopathogenic nematodes emerging from a wax moth cadaver

References

↑ Joyce SA; Brachmann AO; Glazer I; Lango L; Schwär G; Clarke DJ; Bode HB (2008). "Bacterial biosynthesis of a multipotent stilbene". Angew Chem Int Ed Engl. 47 (10): 1942–5. PMID 18236486. doi:10.1002/anie.200705148.
↑ Hu, K; Webster, JM (2000). "Antibiotic production in relation to bacterial growth and nematode development in Photorhabdus--Heterorhabditis infected Galleria mellonella larvae". FEMS microbiology letters. 189 (2): 219–23. PMID 10930742. doi:10.1111/j.1574-6968.2000.tb09234.x.

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pinostilbene (3-methoxyresveratrol) Pterostilbene (3',5'-dimethoxyresveratrol) Rhapontigenin (piceatannol 4'-methyl ether)
Combretastatins	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acylations

3,5-Dihydroxy-4-isopropyl-trans-stilbene

Glycosides

Astringin (Piceatannol 3-O-glucoside)
Isorhapontin (Isorhapontigenin glucoside)
Mulberroside A (Oxyresveratrol diglucoside)

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) trans-Resveratrol-3-O-glucuronide Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)
of rhapontigenin	Rhapontigenin 3-O-rutinoside 4'-Methoxy-(E)-resveratrol 3-O-rutinoside Rhaponticin (Rhapontigenin glucoside)

Oligomeric forms

oligostilbenoids

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3,5-Dihydroxy-4-isopropyl-''trans''-stilbene

See also

References