Chemistry:Valoneic acid dilactone

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Valoneic acid dilactone
Chemical structure of 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
3D model (JSmol)
ChemSpider
UNII
Properties
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).
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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

  1. 1.0 1.1 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
  2. 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

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