Coniferin
Basic information
- CAS
124151-33-3- Standard SMILES
COc1cc(/C=C/CO)ccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
SFLMUHDGSQZDOW-FAOXUISGSA-N- Molecular formula
- C16H22O8
- Average molar mass
- 342.34 g/mol
- Monoisotopic mass
- 342.13146766
Overview
Coniferin is a monosaccharide derivative that is coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. It has a role as a plant metabolite. It is a cinnamyl alcohol beta-D-glucoside, an aromatic ether and a monosaccharide derivative. It is functionally related to a coniferol.
Names & identifiers
- Preferred name
- Coniferin
- IUPAC
- (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]oxane-3,4,5-triol
- English name
- coniferin
- Molecular formula
- C16H22O8
- Molecular weight
- 342.34
Names & synonyms
Coniferin531-29-3Coniferyl alcohol beta-D-glucosideM6616XLU2JCHEBI:16220(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]oxane-3,4,5-triol(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxane-3,4,5-triol(2R,3S,4S,5R,6S)-2-(HYDROXYMETHYL)-6-(4-((E)-3-HYDROXYPROP-1-ENYL)-2-METHOXYPHENOXY)OXANE-3,4,5-TRIOL(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-((1E)-3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy)oxane-3,4,5-triolRefChem:127740(E)-coniferin124151-33-3
Show more names
trans-ConiferinConifosideConiferyl alcohol 4-O-glucoside3-(4beta-D-glucopyranosyloxy-3-met4-[(E)-3-Hydroxy-1-propenyl]-2-methoxyphenyl β-D-glucopyranoside2-Methoxy-4-[(E)-3-hydroxy-1-propenyl]phenyl β-D-glucopyranoside(E)-3-[3-Methoxy-4-(β-D-glucopyranosyloxy)phenyl]-2-propene-1-ol[4-[(E)-3-Hydroxy-1-propenyl]-2-methoxyphenyl]β-D-glucopyranoside
LaricinAbietinConiferoside(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenyl beta-D-glucopyranosideCHEMBL459056coniferyl alcohol-4-O-beta-D-glucopyranosideC16H22O8
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 129 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 404
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
Melting Point186 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 179 · 179-182 °C(Solvent: Water)
- Boiling point
- 625.4 · 625.4±55.0 °C(Predicted)
- Density
- 1.432 · 1.432±0.06 g/cm3(Predicted)
- pka
- 12.81 · 12.81±0.70(Predicted)
- FDA UNII
- 6616 XLU2J · M6616XLU2J
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesEye Irrit. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
UsesA metabolite, and key biosynthetic intermediate for cell wall lignifcation within phenylpropanoid biosynthesis of coniferous trees. A substrate for Coniferin β-D-Glucosidase.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Coniferin is a monosaccharide derivative that is coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. It has a role as a plant metabolite. It is a cinnamyl alcohol beta-D-glucoside, an aromatic ether and a monosaccharide derivative. It is functionally related to a coniferol.
Related reactions
0 records
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Compound notes
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