Dihydroconiferin

Base Information

• Chemical Name: Dihydroconiferin
• CAS No.: 17609-06-2
• Molecular Formula: C₁₆H₂₄O₈
• Molecular Weight: 344.362
• UNII: 05864HE5OB
• ChEMBL ID: CHEMBL460029
• DSSTox Substance ID: DTXSID401316600
• Metabolomics Workbench ID: 78580
• Nikkaji Number: J752.922H
• Wikidata: Q27158365
• Mol file: 17609-06-2.mol

Synonyms:DIHYDROCONIFERIN;17609-06-2;dihydroconiferyl alcohol glucoside;05864HE5OB;UNII-05864HE5OB;4-(3-hydroxypropyl)-2-methoxyphenyl beta-D-glucopyranoside;beta-D-Glucopyranoside, 4-(3-hydroxypropyl)-2-methoxyphenyl;CHEBI:85156;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxypropyl)-2-methoxyphenoxy]oxane-3,4,5-triol;dihydroconiferyl alcohol-4-O-beta-D-glucopyranoside;Glucopyranoside, 4-(3-hydroxypropyl)-2-methoxyphenyl, beta-D-;CHEMBL460029;DTXSID401316600;AKOS040735557;NCGC00385227-01;Q27158365;.BETA.-D-GLUCOPYRANOSIDE, 4-(3-HYDROXYPROPYL)-2-METHOXYPHENYL;GLUCOPYRANOSIDE, 4-(3-HYDROXYPROPYL)-2-METHOXYPHENYL, .BETA.-D-;NCGC00385227-01_C16H24O8_beta-D-Glucopyranoside, 4-(3-hydroxypropyl)-2-methoxyphenyl

Chemical Property of Dihydroconiferin

Chemical Property:

• XLogP3: -1.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 344.14711772
• Heavy Atom Count: 24
• Complexity: 368

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCCO)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)CCCO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of Dihydroconiferin

There total 7 articles about Dihydroconiferin 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: 70.0%

citrusin C (18604-50-7) → 4-(3-hydroxypropyl)-2-methoxyphenyl-O-β-D-glucopyranoside (17609-06-2)

Guidance literature:

citrusin C; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 25 ℃; for 2h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 - 25 ℃; for 1.5h; Inert atmosphere;

DOI:10.1080/14786419.2020.1827399

Reference yield:

C24H32O12 → 4-(3-hydroxypropyl)-2-methoxyphenyl-O-β-D-glucopyranoside (17609-06-2)

Guidance literature:

With potassium hydroxide; In methanol; at 25 ℃;

DOI:10.1080/14786419.2020.1827399

Reference yield:

4-allylguaiacol (97-53-0) → 4-(3-hydroxypropyl)-2-methoxyphenyl-O-β-D-glucopyranoside (17609-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate; tetrabutylammomium bromide / dichloromethane; water / 25 °C

2.1: potassium hydroxide / methanol / 0.5 h

3.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

3.2: 1.5 h / 0 - 25 °C / Inert atmosphere

With dimethylsulfide borane complex; tetrabutylammomium bromide; potassium carbonate; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1080/14786419.2020.1827399

upstream raw materials:

coniferal alcohol

4-allylguaiacol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

citrusin C

Refernces

• 1、 Ushiyama, Masashi,Furuya, Tsutomu. "GLYCOSYLATION OF PHENOLIC COMPOUNDS BY ROOT CULTURE OF PANAX GINSENG". . p. 3009 - 3014. Retrieved 2007/10/02.