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Syringin

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Syringin
Names
IUPAC name 4--2,6-dimethoxyphenyl β-D-glucopyranoside
Systematic IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-{4--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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.120.487 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: QJVXKWHHAMZTBY-GCPOEHJPBY
SMILES
  • O(c1c(OC)cc(/C=C/CO)cc1OC)2O((O)(O)2O)CO
Properties
Chemical formula C17H24O9
Molar mass 372.370 g·mol
Appearance White crystalline solid
Melting point 192 °C (378 °F; 465 K)
Solubility in water Slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 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. 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.

Chemically, it is the glucoside of sinapyl alcohol.

References

  1. ^ 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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