Mesquitol

Mesquitol
Names
	IUPAC name (2R,3S)-Flavan-3,3′,4′,7,8-pentol
	Systematic IUPAC name (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7,8-triol
	Other names (-)-mesquitol
Identifiers
CAS Number	109671-55-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	9208756 ;
PubChem CID	11033582;
UNII	584GQF2MLB ;
	InChI InChI=1S/C15H14O6/c16-9-3-1-7(5-11(9)18)14-12(19)6-8-2-4-10(17)13(20)15(8)21-14/h1-5,12,14,16-20H,6H2/t12-,14+/m0/s1 Key: TXULLYMENMRLHL-GXTWGEPZSA-N ; InChI=1/C15H14O6/c16-9-3-1-7(5-11(9)18)14-12(19)6-8-2-4-10(17)13(20)15(8)21-14/h1-5,12,14,16-20H,6H2/t12-,14+/m0/s1 Key: TXULLYMENMRLHL-GXTWGEPZBX;
	SMILES Oc1ccc(cc1O)[C@H]3Oc2c(O)c(O)ccc2C[C@@H]3O;
Properties
Chemical formula	C15H14O6
Molar mass	290.26 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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	Infobox references

Mesquitol is a flavan-3-ol, a type of flavonoid.^[1]

Prosopis juliflora, an invasive New World mesquite now found in Kenya, has unusually high levels of (-)-mesquitol in its heartwood.^[2]

Mesquitol, with its pyrogallol-type A-ring, is more susceptible to quinone formation at this ring, leading to aryl–aryl bond formation at carbon 5. The structural moieties constitute the proteracacinidin class of proanthocyanidins.^[3] Mesquitol-(5→8)-catechin atropisomers can be isolated from Prosopis glandulosa.^[4]

References

↑ Mesquitol on metabolomics.jp
↑ Unusual amount of (-)-mesquitol from the heartwood of Prosopis juliflora. Sirmah Peter, Dumarcay Stephane, Masson Eric and Gerardin Philippe, Natural Product Research, January 2009, Volume 23, Number 2, pages 183-189, doi:10.1080/14786410801940968
↑ Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Daneel Ferreira and Desmond Slade, Nat. Prod. Rep., 2002, volume 19, pages 517–541, doi:10.1039/b008741f
↑ Synthesis of condensed tannins. Part 17. Oligomeric (2R,3S)-3,3′,4′,7,8-pentahydroxyflavans: atropisomerism and conformation of biphenyl and m-terphenyl analogues from Prosopis glandulosa(‘mesquite’). Esmé Young, Edward V. Brandt, Desmond A. Young, Daneel Ferreira and David G. Roux, J. Chem. Soc., Perkin Trans. 1, 1986, pages 1737-1749, doi:10.1039/P19860001737

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