C14:1-DELTA9-CIS-(L)-HSL

Base Information

• Chemical Name: C14:1-DELTA9-CIS-(L)-HSL
• CAS No.: 202284-87-5
• Molecular Formula: C18H33NO3
• Molecular Weight: 311.46000
• Mol file: 202284-87-5.mol

Synonyms:

Chemical Property of C14:1-DELTA9-CIS-(L)-HSL

Chemical Property:

• Boiling Point: 506.5±39.0 °C(Predicted)
• PKA: 14.70±0.20(Predicted)
• PSA: 55.40000
• Density: 0.99±0.1 g/cm3(Predicted)
• LogP: 4.51010

Purity/Quality:

95% ^*data from raw suppliers

Tetradecanoyl-L-homoserine lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-tetradecanoyl-L-Homoserine lactone (C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. It appears later than shorter acyl chain AHLs in developing biofilms and, like other long chain AHLs, stimulates bacterial growth. C14-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis.
• Uses: Tetradecanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Rhodobacter capsulatus. Tetradecanoyl-L-homoserine lactone and other 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. Tetradecanoyl-L-homoserine lactone is a major modulator for cell communication.

Technology Process of C14:1-DELTA9-CIS-(L)-HSL

There total 6 articles about C14:1-DELTA9-CIS-(L)-HSL 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: 98.0%

L-homoserine lactone hydrochloride (2185-03-7) + n-tetradecanoic acid (544-63-8) → N-tetradecanoyl homoserine lactone (202284-87-5)

Guidance literature:

n-tetradecanoic acid; With sodium hydroxide; In water; pH=9;

L-homoserine lactone hydrochloride; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; at 20 ℃; for 24h;

DOI:10.1021/np900043j

Reference yield: 98.0%

(S)-(-)-α-amino-γ-butyrolactone hydrobromide (6305-38-0,15295-77-9,67580-93-2,110045-70-0) + n-tetradecanoic acid (544-63-8) → N-tetradecanoyl homoserine lactone (202284-87-5)

Guidance literature:

n-tetradecanoic acid; With sodium hydroxide; In water; pH=9;

(S)-(-)-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: 93.7%

(RS)-α-amino-γ-butyrolactone hydrochloride (42417-39-0) + n-tetradecanoic acid (544-63-8) → N-tetradecanoyl homoserine lactone (18725-18-3,98206-80-5,202284-87-5)

Guidance literature:

n-tetradecanoic 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

upstream raw materials:

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

n-tetradecanoic acid

α-amino-γ-butyrolactone hydrobromide

L-homoserine lactone hydrochloride