1-Decen-3-one, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-

Base Information

• Chemical Name: 1-Decen-3-one, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-
• CAS No.: 61871-72-5
• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.375
• Mol file: 61871-72-5.mol

Synonyms:

Chemical Property of 1-Decen-3-one, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Decen-3-one, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-

There total 6 articles about 1-Decen-3-one, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)- 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: 44.5%

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one (1080-12-2,22214-42-2) + hexanal (66-25-1) → (E)-5-hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-1-decen-3-one (61871-72-5,73307-95-6,76095-23-3,132243-18-6) + (1E,4E)-1-(4'-hydroxy-3'-methoxyphenyl)-deca-1,4-dien-3-one

Guidance literature:

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

hexanal; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.foodchem.2014.05.077

Reference yield: 31.0%

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one (1080-12-2,22214-42-2) + hexanal (66-25-1) → (E)-5-hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-1-decen-3-one (61871-72-5,73307-95-6,76095-23-3,132243-18-6)

Guidance literature:

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

hexanal; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Time; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01426

Reference yield:

vanillin (121-33-5,8014-42-4) → (E)-5-hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-1-decen-3-one (61871-72-5,73307-95-6,76095-23-3,132243-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / water / 48 h / 25 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

With sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; water;

DOI:10.1021/acs.jmedchem.7b01426

upstream raw materials:

(E)-3-methoxy-4-trimethylsilyloxybenzylideneacetone

hexanal

vanillin

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

Downstream raw materials:

(+/-)-[6]-gingerol

[6]-shogaol

Refernces

• 1、 Choi, Hyunsuk,Ham, So-Young,Cha, Eunji,Shin, Yujin,Kim, Han-Shin,Bang, Jeong Kyu,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo. "Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents". . p. 9821 - 9837. Retrieved 2017/12/26.
• 2、 Dennif, Phillip,Macleod, Ian,Whiting, Donald A.. "Syntheses of the (+/-)--Gingerols (Pungent Principles of Ginger) and Related Compounds through Regioselective Aldol Condensations: Relative Pungency Assays". . p. 82 - 87. Retrieved 2007/10/02.