Coniferin

Coniferin
Names
	Preferred IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxane-3,4,5-triol
	Other names • β-D-Glucopyranoside 4-(3-hydroxy-1-propenyl)-2-methoxyphenyl; • Coniferyl alcohol β-D-glucoside
Identifiers
CAS Number	531-29-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16220;
ChemSpider	4444067;
ECHA InfoCard	100.230.647
PubChem CID	5280372;
UNII	M6616XLU2J ;
	InChI InChI=1/C16H22O8/c1-22-11-7-9(3-2-6-17)4-5-10(11)23-16-15(21)14(20)13(19)12(8-18)24-16/h2-5,7,12-21H,6,8H2,1H3/b3-2+/t12-,13-,14+,15-,16-/m1/s1 Key: SFLMUHDGSQZDOW-FAOXUISGBA;
	SMILES O(c1c(OC)cc(/C=C/CO)cc1)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO;
Properties
Chemical formula	C16H22O8
Molar mass	342.344 g·mol−1
Appearance	White crystalline solid
Melting point	186 °C (367 °F; 459 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Coniferin is a glucoside of coniferyl alcohol. This white crystalline solid is a metabolite in conifers, serving as an intermediate in cell wall lignification, as well as having other biological roles. It can also be found in the water root extract of Angelica archangelica subsp. litoralis.^[1]

Vanillin was first synthesized from coniferin by chemists Ferdinand Tiemann and Wilhelm Haarmann.

References

^ Lemmich, John; Havelund, Svend; Thastrup, Ole (1983). "Dihydrofurocoumarin glucosides from Angelica archangelica and Angelica silvestris". Phytochemistry. 22 (2): 553–555. Bibcode:1983PChem..22..553L. doi:10.1016/0031-9422(83)83044-1.

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[1] Lemmich, John; Havelund, Svend; Thastrup, Ole (1983). "Dihydrofurocoumarin glucosides from Angelica archangelica and Angelica silvestris". Phytochemistry. 22 (2): 553–555. Bibcode:1983PChem..22..553L. doi:10.1016/0031-9422(83)83044-1.

[1]

v t e Types of monolignols
Aglycones	coniferyl alcohol sinapyl alcohol paracoumaryl alcohol
Glycosides	Coniferin

Names

Preferred IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxane-3,4,5-triol
Other names • β-D-Glucopyranoside 4-(3-hydroxy-1-propenyl)-2-methoxyphenyl • Coniferyl alcohol β-D-glucoside
Identifiers
CAS Number	531-29-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16220
ChemSpider	4444067
ECHA InfoCard	100.230.647
PubChem CID	5280372
UNII	M6616XLU2J^Y
InChI InChI=1/C16H22O8/c1-22-11-7-9(3-2-6-17)4-5-10(11)23-16-15(21)14(20)13(19)12(8-18)24-16/h2-5,7,12-21H,6,8H2,1H3/b3-2+/t12-,13-,14+,15-,16-/m1/s1 Key: SFLMUHDGSQZDOW-FAOXUISGBA
SMILES O(c1c(OC)cc(/C=C/CO)cc1)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO
Properties
Chemical formula	C₁₆H₂₂O₈
Molar mass	342.344 g·mol⁻¹
Appearance	White crystalline solid
Melting point	186 °C (367 °F; 459 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references