mesquitol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 449566525
| Name = Mesquitol
| ImageFile = Mesquitol.svg
| ImageSize = 250px
| ImageName = Chemical structure of mesquitol
| IUPACName = (2R,3S)-Flavan-3,3′,4′,7,8-pentol
| SystematicName = (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7,8-triol
| OtherNames = (−)-mesquitol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 109671-55-8
| CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 584GQF2MLB
| PubChem = 11033582
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 9208756
| SMILES = Oc1ccc(cc1O)[C@H]3Oc2c(O)c(O)ccc2C[C@@H]3O
| 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
| InChIKey = TXULLYMENMRLHL-GXTWGEPZBX
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = TXULLYMENMRLHL-GXTWGEPZSA-N
| MeSHName =
}}
|Section2={{Chembox Properties
| Formula = C15H14O6
| MolarMass = 290.26 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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Mesquitol is a flavan-3-ol, a type of flavonoid.{{cite web|url=http://metabolomics.jp/wiki/FL633CNS0001 |title=Mesquitol |website=metabolomics.jp}}
Prosopis juliflora, an invasive New World mesquite now found in Kenya, has unusually high levels of (−)-mesquitol in its heartwood.{{cite journal|title=Unusual amount of (−)-mesquitol from the heartwood of Prosopis juliflora. |last1=Sirmah |first1=Peter |last2=Dumarçay |first2=Stéphane |last3=Masson |first3=Eric |last4=Gérardin |first4=Philippe |journal=Natural Product Research |date=January 2009 |volume=23 |issue=2 |pages=183–189 |doi=10.1080/14786410801940968}}
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.{{cite journal|title=Oligomeric proanthocyanidins: naturally occurring O-heterocycles |first1=Daneel |last1=Ferreira |first2=Desmond |last2=Slade |journal=Natural Product Reports |date=2002 |volume=19 |pages=517–541 |doi=10.1039/b008741f}} Mesquitol-(5→8)-catechin atropisomers can be isolated from Prosopis glandulosa.{{cite journal|title=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’) |first1=Esmé |last1=Young |first2=Edward V. |last2=Brandt |first3=Desmond A. |last3=Young |first4=Daneel |last4=Ferreira |first5=David G. |last5=Roux |journal=Journal of the Chemical Society, Perkin Transactions 1 |date=1986 |volume=1986 |pages=1737–1749 |doi=10.1039/P19860001737}}