3-Hydroxy-N-(2-oxotetrahydrofuran-3-yl)dodecanamide

Base Information

• Chemical Name: 3-Hydroxy-N-(2-oxotetrahydrofuran-3-yl)dodecanamide
• CAS No.: 182359-60-0
• Molecular Formula: C₁₆H₂₉NO₄
• Molecular Weight: 299.411
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID60467776
• Nikkaji Number: J1.006.269A
• Mol file: 182359-60-0.mol

Synonyms:182359-60-0;3-Hydroxy-N-(2-oxotetrahydrofuran-3-yl)dodecanamide;N-(3-Hydroxydodecanoyl)-DL-homoserine lactone;3-hydroxy-N-(2-oxooxolan-3-yl)dodecanamide;3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)dodecanamide;AGN-PC-00AIFJ;SCHEMBL14169245;DTXSID60467776;3-hydroxy-C12 homoserine lactone;CHEBI:182546;MFCD16875424;J-011670;Dodecanamide, 3-hydroxy-N-(tetrahydro-2-oxo-3-furanyl)-;N-(3-Hydroxydodecanoyl)-DL-homoserine lactone, >=97% (HPLC)

Chemical Property of 3-Hydroxy-N-(2-oxotetrahydrofuran-3-yl)dodecanamide

Chemical Property:

• Boiling Point: 532.2±50.0 °C(Predicted)
• PKA: 14.24±0.20(Predicted)
• PSA: 79.12000
• Density: 1.06±0.1 g/cm3(Predicted)
• LogP: 3.15010
• Storage Temp.: ?20°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 299.20965841
• Heavy Atom Count: 21
• Complexity: 319

Purity/Quality:

98.5% ^*data from raw suppliers

N-(3-Hydroxydodecanoyl)-DL-homoserine lactone ≥97% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(CC(=O)NC1CCOC1=O)O

Technology Process of 3-Hydroxy-N-(2-oxotetrahydrofuran-3-yl)dodecanamide

There total 6 articles about 3-Hydroxy-N-(2-oxotetrahydrofuran-3-yl)dodecanamide 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: 54.0%

N-(3-oxododecanoyl)-L-homoserine lactone (168982-69-2,152833-54-0) → N-(3-hydroxy-dodecanoyl)-L-homoserine lactone (182359-60-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In methanol; at 20 ℃; for 16h; pH=4;

DOI:10.1021/jm2001019

Reference yield:

3-hydroxydodecanoic acid (1883-13-2,53941-38-1) + α-amino-γ-butyrolactone hydrobromide (6305-38-0) → N-(3-hydroxy-dodecanoyl)-L-homoserine lactone (182359-60-0)

Guidance literature:

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

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

DOI:10.1007/s10562-017-2261-8

Reference yield:

HCl-methanol + N-(3-oxododecanoyl)-L-homoserine lactone (168982-69-2,152833-54-0) → N-(3-hydroxy-dodecanoyl)-L-homoserine lactone (182359-60-0)

Guidance literature:

With sodium cyanoborohydride; In methanol;

upstream raw materials:

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

1-decanoic acid

5-(1-hydroxydecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

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

Refernces

• 1、 Leipert, Jan,Treitz, Christian,Leippe, Matthias,Tholey, Andreas. "Identification and Quantification of N-Acyl Homoserine Lactones Involved in Bacterial Communication by Small-Scale Synthesis of Internal Standards and Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry". . p. 2538 - 2547. Retrieved 2017/12/12.
• 2、 Chhabra, Siri Ram,Harty, Chris,Hooi, Doreen S. W.,Daykin, Mavis,Williams, Paul,Telford, Gary,Pritchard, David I.,Bycroft, Barrie W.. "Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators". . p. 97 - 104. Retrieved 2007/10/03.