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Coniferin

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Coniferin
Names
IUPAC name
(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]oxane-3,4,5-triol
Other names
• β-D-Glucopyranoside 4-(3-hydroxy-1-propenyl)-2-methoxyphenyl
• Coniferyl alcohol β-D-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.230.647 Edit this at Wikidata
UNII
  • InChI=1/C16H22O8/c1-22-11-7-9(3-2-6-17)4-5-10(11)23-16-15(21)14(20)13(19)12(8-18)24-16/h2-5,7,12-21H,6,8H2,1H3/b3-2+/t12-,13-,14+,15-,16-/m1/s1
    Key: SFLMUHDGSQZDOW-FAOXUISGBA
  • O(c1c(OC)cc(/C=C/CO)cc1)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO
Properties
C16H22O8
Molar mass 342.35 g/mol
Melting point 186 °C (367 °F; 459 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coniferin is a glucoside of coniferyl alcohol. This white crystalline solid is a metabolite in conifers, serving as an intermediate in cell wall lignification, as well as having other biological roles. It can also be found in the water root extract of Angelica archangelica subsp. litoralis.[1]

Vanillin was first synthesized from coniferin by chemists Ferdinand Tiemann and Wilhelm Haarmann.

References

  1. ^ Dihydrofurocoumarin glucosides from Angelica archangelica and Angelica silvestris. John Lemmich, Svend Havelund and Ole Thastrup, Phytochemistry, 1983, Volume 22, Issue 2, Pages 553–555, doi:10.1016/0031-9422(83)83044-1


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