Syringin

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Syringin
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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
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3D model (JSmol)
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  • 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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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

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  1. ^ a b c Merck Index, 11th Edition, 8997
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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.
  • Page Template:Sister-inline/styles.css has no content.Script error: No such module "Sister project logo". Media related to Script error: No such module "Commons link". at Wikimedia Commons

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