Syringin

Chemical compound From Wikipedia, the free encyclopedia

Syringin is a natural chemical compound first isolated from the bark of lilac (Syringa vulgaris) by Meillet in 1841.[2][1] It has since been found to be distributed widely throughout many types of plants. It is also called eleutheroside B, and is found in Eleutherococcus senticosus (Siberian ginseng). It is also found in dandelion coffee. Syringin may potentially have antidiabetic effects.[3]

Quick facts Names, Identifiers ...
Syringin
Names
IUPAC name
4-[(1E)-3-Hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl β-D-glucopyranoside
Systematic IUPAC name
(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenoxy}oxane-3,4,5-triol
Other names
Eleutheroside B; Ilexanthin A; Ligustrin; Lilacin; Magnolenin; Methoxyconiferine; Sinapyl alcohol 4-O-glucoside; Siringin; Syringoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.120.487 Edit this at Wikidata
EC Number
  • 601-519-0
KEGG
UNII
  • InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1
    Key: QJVXKWHHAMZTBY-GCPOEHJPSA-N
  • InChI=1/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1
    Key: QJVXKWHHAMZTBY-GCPOEHJPBY
  • O(c1c(OC)cc(/C=C/CO)cc1OC)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO
Properties
C17H24O9
Molar mass 372.370 g·mol−1
Appearance White crystalline solid
Melting point 192 °C (378 °F; 465 K)[1]
Slightly soluble[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemically, it is the glucoside of sinapyl alcohol.

References

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