Dihydrodehydroconiferyl alcohol, (7R,8S)-(-)-

Base Information

• Chemical Name: Dihydrodehydroconiferyl alcohol, (7R,8S)-(-)-
• CAS No.: 126253-41-6
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407
• UNII: 2B91L473ZL
• ChEMBL ID: CHEMBL253590
• Metabolomics Workbench ID: 129651
• Nikkaji Number: J616.628H
• Wikidata: Q27254512
• Mol file: 126253-41-6.mol

Synonyms:dihydrodehydrodiconiferylalcohol;lawsonicin;pinonesinol

Chemical Property of Dihydrodehydroconiferyl alcohol, (7R,8S)-(-)-

Chemical Property:

• Boiling Point: 540.9±50.0 °C(Predicted)
• PKA: 9.80±0.35(Predicted)
• PSA: 88.38000
• Density: 1.261±0.06 g/cm3(Predicted)
• LogP: 2.54390
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 360.15728848
• Heavy Atom Count: 26
• Complexity: 433

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Dihydrodehydrodiconiferylalcohol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)CCCO
• Isomeric SMILES: COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O)OC)CCCO

Technology Process of Dihydrodehydroconiferyl alcohol, (7R,8S)-(-)-

There total 21 articles about Dihydrodehydroconiferyl alcohol, (7R,8S)-(-)- 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: 83.3%

(2S,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(E)-3-hydroxy-1-propenyl]-3-hydroxymethyl-7-methoxybenzo[b]furan (97465-82-2) → 2α,3β-7-O-methylcedrusin (14049-57-1,79171-87-2,85165-02-2,125874-72-8,126253-41-6,133318-48-6,28199-69-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 1h; Ambient temperature;

DOI:10.1016/0031-9422(95)95268-Y

Reference yield: 77.0%

methyl 3-[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propanoate → 4-[3-Hydroxymethyl-5-(3-hydroxy-propyl)-7-methoxy-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenol (28199-69-1,85165-02-2,125874-72-8,126253-41-6,133318-48-6,79171-87-2,14049-57-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -15 - 20 ℃;

Reference yield: 74.0%

methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]-propanoate → 2α,3β-7-O-methylcedrusin (14049-57-1,79171-87-2,85165-02-2,125874-72-8,126253-41-6,133318-48-6,28199-69-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2019.07.026

upstream raw materials:

2,3-dihydro-2-(4'-α-L-rhamnopyranosyloxy-3'-methoxyphenyl)-3-hydroxymethyl-7-methoxy-5-benzofuranpropanol

4'-O-α-D-rhamnoside of dihydrodehydroconiferyl alcohol

dihydrodehydrodiconiferyl alcohol‐4‐O‐β‐D‐glucoside

3-(β-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxydihydrobenzofuran

Downstream raw materials:

3',4-di-O-methylcedrusin

2,4'-dihydroxy-3,3'-dimethoxy-5-(3-hydroxypropyl)stilbene

EG-PohG

dihydrodehydrodiconiferyl alcohol triacetate

Refernces

• 1、 Liu, Jin-Long,Wang, Su-Juan,Yu, Min,Zhang, Gui-Jie,Zhang, Yong-Li. "Sesquineolignan and neolignan enantiomers from Triadica sebifera". . . Retrieved 2020/08/06.
• 2、 Zhao, Chunchao,Chen, Jia,Shao, Jianhua,Shen, Jie,Li, Kehuan,Gu, Wenyan,Li, Sihui,Fan, Judi. "Neolignan Constituents with Potential Beneficial Effects in Prevention of Type 2 Diabetes from Viburnum fordiae Hance Fruits". . p. 10421 - 10430. Retrieved 2018/10/15.