137173-46-7

Basic information

• Product Name: DDHL
• Synonyms: C12-HOMOSERINE LACTONE;DDHL;N-DODECANOYL-L-HOMOSERINE LACTONE;C12-HSL, dDHL, N-Dodecanoyl-L-hoMoserine lactone;Dodecanoyl-L-hoMoserine lactone;C12-HSL;N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide;N-Lauroyl-L-homoserine lactone
• CAS NO: 137173-46-7
• Molecular Formula: C16H29NO3
• Molecular Weight: 283.40636
• Mol File: 137173-46-7.mol

Chemical Properties

• Boiling Point: 485.84°C at 760 mmHg
• Flash Point: 247.627°C
• Appearance: /
• Density: 1.005g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.477
• Storage Temp.: ?20°C
• BRN: 9281984
• CAS DataBase Reference: DDHL(CAS DataBase Reference)
• NIST Chemistry Reference: DDHL(137173-46-7)
• EPA Substance Registry System: DDHL(137173-46-7)

Safety Data

• Statements: 53
• WGK Germany: 3
• Hazardous Substances Data: 137173-46-7(Hazardous Substances Data)

Usage

Uses

Used in Bacterial Communication:
DDHL is used as a quorum sensing modulator for regulating cell communication and regulation in various bacterial species. The length of the acyl chain in DDHL is the most significant variable defining its function, with shorter chains displaying opposing actions to the longer chains.
Used in Microbiology Research:
DDHL is used as a research tool for studying the mechanisms of bacterial communication, quorum sensing, and the development of new strategies to control bacterial populations and infections.
Used in Pharmaceutical Development:
DDHL is used as a potential target for the development of new antimicrobial agents that can disrupt bacterial communication and regulation, leading to the control of bacterial infections and the prevention of antibiotic resistance.

Biochem/physiol Actions

N-Dodecanoyl-L-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.

InChI:InChI=1/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1

Upstream product

• 143-07-7 lauric acid 
• 42417-39-0 (RS)-α-amino-γ-butyrolactone hydrochloride 
• 6305-38-0 α-amino-γ-butyrolactone hydrobromide 

Relevant articles and documents

Long-chain acyl-homoserine lactones from Methylobacterium mesophilicum: Synthesis and absolute configuration

The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.

ACYL HOMOSERINE LACTONES FOR INHIBITION OF CELL GROWTH

The present invention provides a method for inhibiting the growth of cancer cells using AHLs of the general formula CX-homoserine lactone where "X" represents a number of between 5 and 14 carbon atoms in the acyl chain of the AHL. The method comprises the step of administering to an individual an amount of an AHL effective to inhibit the growth of cancer cells. Also provided is a method for enhancing the effect of a chemotherapeutic agent comprising the step of administering to an individual the chemotherapeutic agent and an amount of an AHL effective to enhance the cancer cell growth inhibitory effect of the chemotherapeutic agent.