N-(3-Hydroxydecenoyl)-DL-hoMoserine lactone

Base Information

• Chemical Name: N-(3-Hydroxydecenoyl)-DL-hoMoserine lactone
• CAS No.: 929222-14-0
• Molecular Formula: C₁₄H₂₅NO₄
• Molecular Weight: 271.357
• Mol file: 929222-14-0.mol

Synonyms:

Chemical Property of N-(3-Hydroxydecenoyl)-DL-hoMoserine lactone

Chemical Property:

• PSA: 79.12000
• LogP: 2.36990
• Storage Temp.: ?20°C

Purity/Quality:

N-(3-Hydroxydecanoyl)-DL-homoserine lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(3-Hydroxydecenoyl)-DL-hoMoserine lactone

There total 5 articles about N-(3-Hydroxydecenoyl)-DL-hoMoserine lactone 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:

3-hydroxydecanoic acid (5561-87-5,19525-80-5,19526-23-9,33044-91-6,14292-26-3) + α-amino-γ-butyrolactone hydrobromide (6305-38-0) → N-(3-hydroxy-decanoyl)-L-homoserine lactone (192883-12-8,929222-14-0)

Guidance literature:

α-amino-γ-butyrolactone hydrobromide; With N-ethyl-N,N-diisopropylamine; In tert-Amyl alcohol; at 70 ℃; for 0.5h;

3-hydroxydecanoic acid; With sodium sulfate; In tert-Amyl alcohol; at 70 ℃; for 120h; stereospecific reaction;

DOI:10.1007/s10562-017-2261-8

Reference yield:

S-(5’-adenosyl)-L-methionine chloride dihydrochloride (86867-01-8) + (R)-S-(3-hydroxydecanoyl)-N-pantothenoylcysteamine → N-(3-hydroxy-decanoyl)-L-homoserine lactone (192883-12-8,929222-14-0)

Guidance literature:

With Phaeobacter inhibens PgaI₂; In dimethyl sulfoxide; glycerol; at 28 ℃; for 5h; Reagent/catalyst; Enzymatic reaction;

DOI:10.3762/bjoc.14.112

Reference yield:

2,2-dimethyl-5-octanoyl-1,3-dioxane-4,6-dione (103576-44-9) → N-(3-hydroxy-decanoyl)-L-homoserine lactone (192883-12-8,929222-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 70 °C

2: sodium cyanoborohydride; hydrogenchloride / methanol / pH 3 - 4

With hydrogenchloride; sodium cyanoborohydride; In methanol; acetonitrile;

DOI:10.1007/s13361-017-1777-x

upstream raw materials:

2,2-dimethyl-5-octanoyl-1,3-dioxane-4,6-dione

N-(3-oxodecanoyl)-L-homoserine lactone

Octanoic acid

3-hydroxydecanoic acid

Refernces

• 1、 Ziesche, Lisa,Rinkel, Jan,Dickschat, Jeroen S.,Schulz, Stefan. "Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria". supporting information. p. 1309 - 1316. Retrieved 2018/06/13.