Mesquitol: Difference between revisions
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| Name = Mesquitol |
| Name = Mesquitol |
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| ImageFile = Mesquitol.svg |
| ImageFile = Mesquitol.svg |
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| ImageSize = 250px |
| ImageSize = 250px |
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| ImageName = Chemical structure of mesquitol |
| ImageName = Chemical structure of mesquitol |
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| IUPACName = 3 |
| IUPACName = (2''R'',3''S'')-Flavan-3,3′,4′,7,8-pentol |
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| SystematicName = (2''R'',3''S'')-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2''H''-1-benzopyran-3,7,8-triol |
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| OtherNames = (-)-mesquitol<!-- <br> --> |
| OtherNames = (-)-mesquitol<!-- <br> --> |
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|Section1= |
|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 109671-55-8 |
| CASNo = 109671-55-8 |
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| CASNoOther = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASOther = |
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| UNII = 584GQF2MLB |
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| PubChem = 11033582 |
| PubChem = 11033582 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| SMILES = Oc(c3)c(O)cc(c3)C(O1)C(O)Cc(c2)c1c(O)c(O)c2 |
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| ChemSpiderID = 9208756 |
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| SMILES = Oc1ccc(cc1O)[C@H]3Oc2c(O)c(O)ccc2C[C@@H]3O |
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| 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 |
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| InChIKey = TXULLYMENMRLHL-GXTWGEPZBX |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = TXULLYMENMRLHL-GXTWGEPZSA-N |
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|Section2= |
|Section2={{Chembox Properties |
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| Formula = C<sub>15</sub>H<sub>14</sub>O<sub>6</sub> |
| Formula = C<sub>15</sub>H<sub>14</sub>O<sub>6</sub> |
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| MolarMass = 290.26 g/mol |
| MolarMass = 290.26 g/mol |
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| ExactMass = 290.079038 u |
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| Appearance = |
| Appearance = |
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| Density = |
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'''Mesquitol''' is a [[flavan- |
'''Mesquitol''' is a [[flavan-3-ol]], a type of flavonoid.<ref>[http://metabolomics.jp/wiki/FL633CNS0001 Mesquitol on metabolomics.jp]</ref> |
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''[[Prosopis juliflora]]'', |
''[[Prosopis juliflora]]'', an invasive [[New World]] [[mesquite]] now found in Kenya, has unusually high levels of (-)-mesquitol in its heartwood.<ref>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}}</ref> |
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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 [[proanthocyanidin]]s.<ref>Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Daneel Ferreira and Desmond Slade, Nat. Prod. Rep., 2002, volume 19, pages 517–541, {{doi|10.1039/b008741f}}</ref> [[Mesquitol-(5→8)-catechin]] [[atropisomer]]s can be isolated |
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from ''[[Prosopis glandulosa]]''.<ref>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}}</ref> |
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