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Syringin

Syringin is a natural chemical compound first isolated from the bark oflilac (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 calledeleutheroside B, and is found inEleutherococcus senticosus (Siberian ginseng). It is also found indandelion coffee. Syringin may potentially have antidiabetic effects.[3]

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 InfoCard100.120.487Edit 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 mass372.370 g·mol−1
AppearanceWhite crystalline solid
Melting point192 °C (378 °F; 465 K)[1]
Slightly soluble[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).

Chemically, it is theglucoside ofsinapyl alcohol.

References

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  1. ^abcMerck 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

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