N-Octadecanoyl-L-homoserine lactone
| Code | Size | Price |
|---|
| CDX-O0137-M010 | 10 mg | £72.00 |
Quantity:
| CDX-O0137-M050 | 50 mg | £255.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
Short Term: +4°C, Long Term: -20°C
Documents
Further Information
Alternate Names/Synonyms:
C18-L-HSL; N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octadecanamide
Appearance:
White to off-white powder.
CAS:
479050-96-9
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light and moisture.
Hazards:
H302
InChi:
InChI=1S/C22H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)23-20-18-19-26-22(20)25/h20H,2-19H2,1H3,(H,23,24)/t20-/m0/s1
InChiKey:
HGMDJDYXARRSKB-FQEVSTJZSA-N
Long Description:
Chemical. CAS: 479050-96-9. Formula: C22H41NO3. MW: 367.6. Synthetic. N-Octadecanoyl-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. C18-HSL is a lipophilic, long acyl side-chain bearing AHL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes. It tends to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by extracellular outer membrane vesicles.
MDL:
MFCD11976914
Molecular Formula:
C22H41NO3
Molecular Weight:
367.6
Package Type:
Vial
Product Description:
N-Octadecanoyl-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. C18-HSL is a lipophilic, long acyl side-chain bearing AHL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes. It tends to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by extracellular outer membrane vesicles.
Purity:
>97% (HPLC)
Signal word:
Warning
SMILES:
O=C(N[C@@H]1C(OCC1)=O)CCCCCCCCCCCCCCCCC
Solubility Chemicals:
Soluble in ethanol, methanol, DMF or DMSO. Insoluble in water.
Source / Host:
Synthetic
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
(1) J.P. Pearson, et al.; J. Bacteriol. 181, 1203 (1999) | (2) M. Marketon, et al.; J. Bacteriol. 184, 5686 (2002) | (3) J.E. Gonzalez & N.D. Keshavan; Microbiol. Mol. Biol. Rev. 70, 859 (2006) | (4) T.A. Gould, et al.; J. Bacteriol. 188, 773 (2006) | (5) C.G.N. Penalver, et al.; FEBS Lett. 580, 561 (2006) | (6) L. Mashburn-Warren & M. Whiteley; Mol. Microbiol. 61, 839 (2006) | (7) L. Cegelski, et al.; Nat. Rev. Microbiol. 6, 17 (2008)