Prunetin

Prunetin
Names


IUPAC name 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
Other names Prunusetin 4',5-dihydroxy-7-methoxyisoflavone 5,4'-dihydroxy-7-methoxyisoflavone
Identifiers
CAS Number	552-59-0^Y=
ChEBI	CHEBI:8600^N
ChEMBL	ChEMBL491174^N
ChemSpider	4445116^N
EC Number	209-018-5
IUPHAR/BPS	6919
Jmol interactive 3D	Image
KEGG	C10521^N
PubChem	5281804
InChI InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3^N Key: KQMVAGISDHMXJJ-UHFFFAOYSA-N^N InChI=1/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3 Key: KQMVAGISDHMXJJ-UHFFFAOYAR
SMILES COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O
Properties
Chemical formula	C₁₆H₁₂O₅
Molar mass	284.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata (the Oregon cherry).^[1] Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores.^[2] It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.^[3]

Glycosides

8-C-glucosyl prunetin, isolated from the leaves of Dalbergia hainanensis^[4]

References

↑ Isoflavones. III. The structure of prunetin and a new synthesis of genistein. R. L. Shriner, C. J. Hull, J. Org. Chem., 1945, 10 (4), pp 288–291
↑ Aphanomyces euteiches zoospore attractant isolated from pea root; prunetin. Ryozo Yokosawa, Shiro Kuninaga and Harua Sekizaki, Ann. Phytopath. Soc. Japan 52:809-816 (1986)
↑ Allosteric inhibition of human liver aldehyde dehydrogenase by the isoflavone prunetin. Sheikh S. and Weiner H., Biochemical pharmacology, 1997, vol. 53, no4, pp. 471-478
↑ Conformational Study of 8-C-glucosyl-prunetin by Dynamic NMR Spectroscopy. Pei Cheng Zhang, Ying Hong Wang, Xin Liu, Xiang Yi, Ruo Yun Chen and De Quan Yu, Chinese Chemical Letters Vol. 13, No. 7, pp 645 – 648, 2002

Isoflavones and their glycosides

Isoflavones	Daidzein Genistein Irilone Orobol Pseudobaptigenin Anagyroidisoflavone A and B

O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin

Glycosides	Daidzin Genistin Iridin Ononin Puerarin Sophoricoside Tectoridin

Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone

Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone

Misc	Rotenoids

Synthetic	Ipriflavone

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