N-3-Oxo-Dodecanoyl-L-Homoserine Lactone

Base Information

• Chemical Name: N-3-Oxo-Dodecanoyl-L-Homoserine Lactone
• CAS No.: 168982-69-2
• Molecular Formula: C16H27NO4
• Molecular Weight: 297.395
• Hs Code.: 2932209090
• European Community (EC) Number: 630-657-4
• DSSTox Substance ID: DTXSID90390604
• Nikkaji Number: J641.803A
• Wikidata: Q27097543
• Metabolomics Workbench ID: 4641
• ChEMBL ID: CHEMBL8483
• Mol file: 168982-69-2.mol

Synonyms:3-oxo-C12-HSL;3-oxo-C8-HSL;3O-C12-HSL;N-(3-oxododecanoyl)-homoserine lactone;N-(3-oxododecanoyl)-L-homoserine lactone;N-(3-oxododecanoyl)homoserine lactone;N-3-oxododecanoyl-L-homoserine lactone;N3-ODDHL

Chemical Property of N-3-Oxo-Dodecanoyl-L-Homoserine Lactone

Chemical Property:

• Boiling Point: 519.4 °C at 760 mmHg
• Flash Point: 267.924 °C
• PSA: 72.47000
• Density: 1.066 g/cm³
• LogP: 2.90890
• Storage Temp.: -20°C
• Solubility.: ≤20mg/ml in DMSO;20mg/ml in dimethyl formamide
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 297.19400834
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

97% ^*data from raw suppliers

N-(3-Oxododecanoyl)-L-homoserineLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(=O)CC(=O)NC1CCOC1=O
• Isomeric SMILES: CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• Description: N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) is a bacterial quorum-sensing signaling molecule produced by P. aeruginosa and strains of the B. cepacia complex. It induces the production of IL-8 in 16HBE human bronchial epithelial cells when used at a concentration of 100 μM. Supernatants from 3-oxo-C12-HSL-stimulated 16HBE cells induce chemotaxis of isolated human neutrophils. 3-oxo-C12-HSL has been found in respiratory secretions from patients with cystic fibrosis infected with P. aeruginosa.
• Uses: N-(3-Oxododecanoyl)-L-homoserine Lactone is a bacterial quorum sensing signal molecule. Inhibits lymphocyte proliferation and TNF-α and IL-12 production by LPS-stimulated macrophages. Inhibits or promotes antibody production at high and low concentrations, respectively, in keyhole limpet hemocyanin (KLH)-stimulated spleen cells.

Technology Process of N-3-Oxo-Dodecanoyl-L-Homoserine Lactone

There total 20 articles about N-3-Oxo-Dodecanoyl-L-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: 90.0%

(S)-2-(2-nonyl-1,3-dioxolan-2-yl)-N-(2-oxotetrahydrofuran-3-yl)acetamide (182359-61-1) → N-(3-oxododecanoyl)-L-homoserine lactone (168982-69-2,152833-54-0)

Guidance literature:

With perchloric acid; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/ejoc.201300084

Reference yield: 62.0%

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

Guidance literature:

Reference yield: 21.0%

3-oxo-dodecanoic acid (61058-75-1) + 3-deoxy-L-glycero-tetronolactone (19444-84-9,52079-23-9,56881-90-4,112709-14-5) → N-(3-oxododecanoyl)-L-homoserine lactone (168982-69-2,152833-54-0)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jm500215s

upstream raw materials:

3-oxo-dodecanoic acid

L-homoserine lactone

L-homoserine lactone hydrochloride

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

Downstream raw materials:

N-(3-hydroxy-dodecanoyl)-L-homoserine lactone