N-dodecanoyl-L-Homoserine lactone

Base Information

• Chemical Name: N-dodecanoyl-L-Homoserine lactone
• CAS No.: 137173-46-7
• Molecular Formula: C16H29NO3
• Molecular Weight: 283.40600
• DSSTox Substance ID: DTXSID001299632
• Nikkaji Number: J767.326D
• Wikidata: Q76415302
• Metabolomics Workbench ID: 78430
• ChEMBL ID: CHEMBL8755
• Mol file: 137173-46-7.mol

Synonyms:N-dodecanoyl-L-Homoserine lactone;137173-46-7;N-[(3S)-2-oxooxolan-3-yl]dodecanamide;Dodecanoyl-L-homoserine lactone;CHEMBL8755;Dodecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-;N-(dodecanoyl)-homoserine lactone;C12-HSL;N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide;dDHL;EWM;(S)-N-dodecanoyl-HSL;SCHEMBL131898;WILLZMOKUUPJSL-AWEZNQCLSA-N;DTXSID001299632;BDBM50351252;LMFA08030014;MFCD11976890;AS-68634;HY-118697;CS-0068272;(S)-N-(2-Oxotetrahydrofuran-3-yl)dodecanamide;F87074;J-006969;N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide;N-Dodecanoyl-L-homoserine lactone, >=96% (HPLC)

Chemical Property of N-dodecanoyl-L-Homoserine lactone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 485.84oC at 760 mmHg
• Flash Point: 247.627oC
• PSA: 55.40000
• Density: 1.005g/cm3
• LogP: 3.72990
• Storage Temp.: ?20°C
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 283.21474379
• Heavy Atom Count: 20
• Complexity: 291

Purity/Quality:

97% ^*data from raw suppliers

N-Dodecanoyl-L-homoserine lactone ≥98%, powder ^*data from reagent suppliers

Safty Information:

• Statements: 53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(=O)NC1CCOC1=O
• Isomeric SMILES: CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
• Uses: Dodecanoyl-L-homoserine lactone was confirmed to be an active quorum sensing modulator first recognised in Sinorhizobium meliloti. N-Acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorter chains displaying opposing actions to the longer chains. Dodecanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Sinorhizobium meliloti. N-Acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorter chains displaying opposing actions to the longer chains. Dodecanoyl-L-homoserine lactone is a modulator of cell communication and regulation.

Technology Process of N-dodecanoyl-L-Homoserine lactone

There total 3 articles about N-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: 71.5%

lauric acid (143-07-7) + (RS)-α-amino-γ-butyrolactone hydrochloride (42417-39-0) → N-dodecanoyl-DL-homoserine lactone (137173-46-7,18627-38-8)

Guidance literature:

lauric acid; With sodium hydroxide; In water; pH=9;

(RS)-α-amino-γ-butyrolactone hydrochloride; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; at 20 ℃; for 24h;

DOI:10.1021/np900043j

Reference yield: 71.5%

lauric acid (143-07-7) + α-amino-γ-butyrolactone hydrobromide (6305-38-0) → N-dodecanoyl-DL-homoserine lactone (137173-46-7,18627-38-8)

Guidance literature:

lauric acid; With sodium hydroxide; In water; pH=9;

α-amino-γ-butyrolactone hydrobromide; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; at 20 ℃; for 24h;

DOI:10.1021/np900043j

Reference yield:

→ N-dodecanoyl-DL-homoserine lactone (137173-46-7,18627-38-8)

Guidance literature:

2-Amino-4-butyrolacton*HBr, Dodecanoylchlorid;

upstream raw materials:

lauric acid

(RS)-α-amino-γ-butyrolactone hydrochloride

α-amino-γ-butyrolactone hydrobromide