2(3H)-Furanone,5-[(3,4-dihydroxyphenyl)methyl]dihydro-,(5R)-(9CI)

Base Information

• Chemical Name: 2(3H)-Furanone,5-[(3,4-dihydroxyphenyl)methyl]dihydro-,(5R)-(9CI)
• CAS No.: 191666-22-5
• Molecular Formula: C11H12 O4
• Molecular Weight: 208.214
• Mol file: 191666-22-5.mol

Synonyms:2(3H)-Furanone,5-[(3,4-dihydroxyphenyl)methyl]dihydro-,(5R)-(9CI)

Chemical Property of 2(3H)-Furanone,5-[(3,4-dihydroxyphenyl)methyl]dihydro-,(5R)-(9CI)

Chemical Property:

• PSA: 66.76000
• LogP: 1.34590
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

(4R)-5-(3'',4''-Dihydroxyphenyl)-γ-valerolactone((-)-EpicatechinMetabolite) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A metabolite of (-)-Epicatechin (E582260).

Technology Process of 2(3H)-Furanone,5-[(3,4-dihydroxyphenyl)methyl]dihydro-,(5R)-(9CI)

There total 16 articles about 2(3H)-Furanone,5-[(3,4-dihydroxyphenyl)methyl]dihydro-,(5R)-(9CI) 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: 95.0%

(-)(R)-5-[(4-benzyloxy)-3-hydroxyphenyl]dihydrofuran-2(3H)one → (4R)-5-(3,4-dihydroxyphenyl)-γ-valerolactone (191666-22-5,83993-39-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 3h; Sealed tube;

DOI:10.1002/adsc.201500705

Reference yield: 87.0%

ethyl (4R)-5-{3,4-bis[tert-butyl(dimethyl)silyloxy]phenyl}-4-hydroxypentanoate (1235828-36-0) → (4R)-5-(3,4-dihydroxyphenyl)-γ-valerolactone (191666-22-5,83993-39-9)

Guidance literature:

With toluene-4-sulfonic acid; In water; benzene; for 4h; Molecular sieve; Reflux;

DOI:10.1055/s-0029-1218671

Reference yield: 62.0%

(R)-5-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one → (4R)-5-(3,4-dihydroxyphenyl)-γ-valerolactone (191666-22-5,83993-39-9)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.3390/molecules25092215

upstream raw materials:

(-)-epicatechin gallate

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

ethyl (4R)-5-{3,4-bis[tert-butyl(dimethyl)silyloxy]phenyl}-4-hydroxypentanoate

1,2-dimethoxy-4-(E)-propenylbenzene

Downstream raw materials:

5-(3′,4′,5′-trihydroxyphenyl)valeric acid

Refernces

• 1、 Hur, Joonseong,Kim, A-Ram,Kim, Hyun Su,Kim, Tae-Aug,Kim, Taewoo,Lim, Changjin,Sim, Jaehoon,Suh, Young-Ger. "Concise synthesis of catechin metabolites 5-(30,40-dihydroxyphenyl)-γ-valerolactones (dhpv) in optically pure form and their stereochemical effects on skin wrinkle-reducing activities". . . Retrieved 2020/04/29.
• 2、 Hamada, Masahiro,Furuno, Ai,Nakano, Sousuke,Kishimoto, Takao,Nakajima, Noriyuki. "Synthesis of optically pure lactone metabolites of tea catechins". experimental part. p. 1512 - 1520. Retrieved 2010/09/16.