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 ;
CompTox Dashboard (EPA)	DTXSID10551896 ;
	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). verify (what is ?) 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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v t e Flavan-3-ols and their glycosides
Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Fisetinidol Gallocatechin Guibourtinidol Mesquitol Oritin Robinetinidol
O-methylated flavan-3ols	Meciadanol (3-O-methylcatechin) Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
Glycosides	Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside) Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside) Catechin-3-O-glucoside Catechin-3'-O-glucoside Catechin-4'-O-glucoside Catechin-5-O-glucoside Catechin-7-O-glucoside (+)-Catechin 7-O-β-D-xylopyranoside Epicatechin-3′-O-glucoside Glochiflavanoside A, B, C D Polydine ((+)-catechin 7-O-α-L-arabinoside) Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Gallate esters	Epigallocatechin gallate Gallocatechin gallate
Misc.	Thearubigins

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^Y
3D model (JSmol)	Interactive image
ChemSpider	9208756^N
PubChem CID	11033582
UNII	584GQF2MLB^Y
CompTox Dashboard (EPA)	DTXSID10551896
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^N Key: TXULLYMENMRLHL-GXTWGEPZSA-N^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). N verify (what is ^YN ?) Infobox references