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{{chembox
{{chembox
| Verifiedfields = changed
⚫
| verifiedrevid = 423617535
| Watchedfields = changed
⚫
| verifiedrevid = 449566525
| Name = Mesquitol
| Name = Mesquitol
| ImageFile = Mesquitol.svg
| ImageFile = Mesquitol.svg
| ImageSize = 250px
| ImageSize = 250px
| ImageName = Chemical structure of mesquitol
| ImageName = Chemical structure of mesquitol
| IUPACName = 3,4-Dihydro-2alpha- (3,4-dihydroxyphenyl) -2H-1-benzopyran-3beta,7,8-triol
| IUPACName = (2''R'',3''S'')-Flavan-3,3′,4′,7,8-pentol
| SystematicName = (2''R'',3''S'')-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2''H''-1-benzopyran-3,7,8-triol
| OtherNames = (-)-mesquitol<!-- <br> -->
| OtherNames = (-)-mesquitol<!-- <br> -->
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 109671-55-8
| CASNo = 109671-55-8
| CASNo_Ref =
| CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| CASOther =
| UNII = 584GQF2MLB
| PubChem = 11033582
| PubChem = 11033582
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| SMILES = Oc(c3)c(O)cc(c3)C(O1)C(O)Cc(c2)c1c(O)c(O)c2
| InChI =
| 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 =
| MeSHName =
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| 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>
| MolarMass = 290.26 g/mol
| MolarMass = 290.26 g/mol
| ExactMass = 290.079038 u
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt = <!-- °C -->
| MeltingPt =
| BoilingPt = <!-- °C -->
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
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'''Mesquitol''' is a [[flavan-3-ol]], a type of flavonoid.<ref>[http://metabolomics.jp/wiki/FL633CNS0001 Mesquitol on metabolomics.jp]</ref>
'''Mesquitol''' is a [[flavan-3-ol]], a type of flavonoid.<ref>[http://metabolomics.jp/wiki/FL633CNS0001 Mesquitol on metabolomics.jp]</ref>


''[[Prosopis juliflora]]'', a [[mesquite]] found in Kenya, shows unusual amount of (-)-mesquitol from 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>
''[[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>


Mesquitol 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, 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
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>


== References ==
== References ==
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{{Natural-phenol-stub}}
{{aromatic-stub}}

Latest revision as of 23:21, 4 May 2023

Mesquitol
Chemical structure of 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
3D model (JSmol)
ChemSpider
UNII
  • 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
  • Oc1ccc(cc1O)[C@H]3Oc2c(O)c(O)ccc2C[C@@H]3O
Properties
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 checkY☒N ?)

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

[edit]
  1. ^ Mesquitol on metabolomics.jp
  2. ^ 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
  3. ^ Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Daneel Ferreira and Desmond Slade, Nat. Prod. Rep., 2002, volume 19, pages 517–541, doi:10.1039/b008741f
  4. ^ 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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