Oxyresveratrol

Oxyresveratrol
Names

Preferred IUPAC name 4-[(E)-2-(3,5-Dihydroxyphenyl)ethen-1-yl]benzene-1,3-diol
Other names 2,3',4,5'-Tetrahydroxy-trans-stilbene
Identifiers
CAS Number	29700-22-9^Y
3D model (JSmol)	Interactive image
ChemSpider	4445033
ECHA InfoCard	100.108.380
KEGG	C10273
MeSH	C034912
PubChem CID	5281717
UNII	6V071CP5CR^Y
CompTox Dashboard (EPA)	DTXSID801030442
InChI InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+ Key: PDHAOJSHSJQANO-OWOJBTEDSA-N
SMILES C1=CC(=C(C=C1O)O)C=CC2=CC(=CC(=C2)O)O
Properties
Chemical formula	C₁₄H₁₂O₄
Molar mass	244.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Oxyresveratrol is a stilbenoid. It is found in the heartwood of Artocarpus lakoocha and in the traditional drug 'Puag-Haad' made from it.^[1] It is also the aglycone of mulberroside A, a compound found in Morus alba, the white mulberry.^[2]

Oxyresveratrol is a potent tyrosinase inhibitor.^[2]

References

^ Maneechai, S; Likhitwitayawuid, K; Sritularak, B; Palanuvej, C; Ruangrungsi, N; Sirisa-Ard, P (2009). "Quantitative analysis of oxyresveratrol content in Artocarpus lakoocha and 'Puag-Haad'". Medical Principles and Practice. 18 (3): 223–7. doi:10.1159/000204354. PMID 19349726. S2CID 29232919.
^ ^a ^b Kim, JK; Kim, M; Cho, SG; Kim, MK; Kim, SW; Lim, YH (2010). "Biotransformation of mulberroside a from Morus alba results in enhancement of tyrosinase inhibition". Journal of Industrial Microbiology & Biotechnology. 37 (6): 631–7. doi:10.1007/s10295-010-0722-9. PMID 20411402. S2CID 21236818.

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

Oxyresveratrol
Piceatannol

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)