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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9380;
ChemSpider	4475831;
ECHA InfoCard	100.120.487
PubChem CID	5316860;
UNII	I6F5B11C96 ;
CompTox Dashboard (EPA)	DTXSID2042438 ;
	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;
	SMILES 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)
Solubility in water	Slightly soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

^ ^a ^b ^c Merck Index, 11th Edition, 8997
^ 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.
^ 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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[Merck-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.

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