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Valoneic acid dilactone

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Valoneic acid dilactone
Names

Preferred IUPAC name 3,4,5-Trihydroxy-2-[(3,7,8-trihydroxy-5,10-dioxo-5,10-dihydro[1]benzopyrano[5,4,3-cde][1]benzopyran-2-yl)oxy]benzoate
Other names Valoneic acid bislactone Valoneic acid bilactone
Identifiers
CAS Number	60202-70-2^Y
3D model (JSmol)	Interactive image
ChemSpider	8327382^N
PubChem CID	10151874
UNII	UH5C3DT5LR^Y
CompTox Dashboard (EPA)	DTXSID60436184
InChI InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29)^N Key: BPAOAXAAABIQKR-UHFFFAOYSA-N^N InChI=1/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29) Key: BPAOAXAAABIQKR-UHFFFAOYAM
SMILES Oc1cc5c(=O)oc3c(O)c(Oc4c(C(=O)O)cc(O)c(O)c4O)cc2c3c5c(c1O)oc2=O
Properties
Chemical formula	C₂₁H₁₀O₁₃
Molar mass	470.28 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

Valoneic acid dilactone is a hydrolysable tannin that can be isolated from the heartwood of Shorea laevifolia^[1] and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).^[2]

It shows an inhibitory effect on 5α-reductase,^[1] an enzyme involved in steroids metabolism and prostate cancer.

References[edit]

^ ^a ^b 5A-Reductase inhibitory tannin-related compounds isolated from Shorea laevifolia. Yoshio Hirano, Ryuichiro Kondo and Kokki Sakai, Journal of wood science, Volume 49, Number 4, pp.339-343,doi:10.1007/s10086-002-0481-y

^ Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. Pirjo Mämmelä, Heikki Savolainenb, Lasse Lindroosa, Juhani Kangasd and Terttu Vartiainen, Journal of Chromatography A, Volume 891, Issue 1, 1 September 2000, Pages 75-83, doi:10.1016/S0021-9673(00)00624-5