Syringin

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
CAS Number
  • 118-34-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:9380
ChemSpider
  • 4475831
ECHA InfoCard 100.120.487 Edit this at Wikidata
PubChem CID
  • 5316860
UNII
  • I6F5B11C96 checkY
CompTox Dashboard (EPA)
  • DTXSID2042438 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C17H24O9
Molar mass 372.370 g·mol−1
Appearance White crystalline solid
Melting point 192 °C (378 °F; 465 K)[1]
Solubility in water
 Slightly soluble[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

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]

Chemically, it is the glucoside of sinapyl alcohol.

References

  1. ^ a b c Merck Index, 11th Edition, 8997
  2. ^ Park, Hee-Juhn; Jung, Won-Tae; Basnet, Purusotam; Kadota, Shigetoshi; Namba, Tsuneo (1996). "Syringin 4-O-β-Glucoside, a New Phenylpropanoid Glycoside, and Costunolide, a Nitric Oxide Synthase Inhibitor, from the Stem Bark of Magnolia sieboldii". Journal of Natural Products. 59 (12): 1128–1130. doi:10.1021/np960452i. PMID 8988596.
  3. ^ Sundaram Chinna Krishnan, Shanmuga; Pillai Subramanian, Iyyam; Pillai Subramanian, Sorimuthu (2014). "Isolation, characterization of syringin, phenylpropanoid glycoside from Musa paradisiaca tepal extract and evaluation of its antidiabetic effect in streptozotocin-induced diabetic rats". Biomedicine & Preventive Nutrition. 4 (2): 105–111. doi:10.1016/j.bionut.2013.12.009.

External links

  • Media related to Syringin at Wikimedia Commons
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