Coniferin

Base Information

• Chemical Name: Coniferin
• CAS No.: 124151-33-3
• Molecular Formula: C16H22O8
• Molecular Weight: 342.346
• European Community (EC) Number: 803-885-9
• UNII: M6616XLU2J
• Nikkaji Number: J6.979E,J246.057B
• Wikipedia: Coniferin
• Wikidata: Q358968
• Metabolomics Workbench ID: 42476
• ChEMBL ID: CHEMBL459056
• Mol file: 124151-33-3.mol

Synonyms:coniferin;coniferyl alcohol beta-D-glucoside

Chemical Property of Coniferin

Chemical Property:

• Melting Point: 184.5 - 185.5 °C (methanol)
• Boiling Point: 625.4±55.0 °C(Predicted)
• PKA: 12.81±0.70(Predicted)
• PSA: 128.84000
• Density: 1.432±0.06 g/cm3(Predicted)
• LogP: -1.12060
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 342.13146766
• Heavy Atom Count: 24
• Complexity: 404

Purity/Quality:

97% ^*data from raw suppliers

Coniferin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CCO)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: A metabolite, and key biosynthetic intermediate for cell wall lignifcation within phenylpropanoid biosynthesis of coniferous trees. A substrate for Coniferin β-D-Glucosidase.

Technology Process of Coniferin

There total 16 articles about Coniferin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.1%

[4-(3-hydroxy-trans-propenyl)-2-methoxy-phenyl]-(tetra-O-acetyl-β-D-glucopyranoside) (62604-84-6) → coniferin (124151-33-3)

Guidance literature:

With sodium methylate; In methanol; for 3h;

DOI:10.1055/s-1998-2009

Reference yield:

4-(3′-hydroxypropenyl)-2-methoxyphenyl β-D-{6″-O-[(1?S,2?R,4?S, 6?R,7?E,9?Z)-4'''-dihydrophaseyl]}glucopyranoside → coniferin (109361-66-2,124151-33-3,531-29-3,39937-31-0) + (1′R,3′S,5′R,8′S,2Z,4E)-dihydrophaseic acid

Guidance literature:

With water; lithium hydroxide; In methanol; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.phytochem.2019.03.021

Reference yield:

UDP-glucose (133-89-1) + coniferol (458-35-5) → coniferin (109361-66-2,124151-33-3,531-29-3,39937-31-0)

Guidance literature:

With magnesium chloride; BSA; In dimethyl sulfoxide; pH=7.5;

DOI:10.1074/jbc.M115.659631

upstream raw materials:

[4-(3-hydroxy-trans-propenyl)-2-methoxy-phenyl]-(tetra-O-acetyl-β-D-glucopyranoside)

methanol

4-(3-acetoxy-1-propenyl)-2-methoxyphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

coniferal alcohol

Downstream raw materials:

coniferyl aldehyde 4-O-β-D-glucopyranoside

coniferal alcohol

D-glucose