Chemodex

N-Hexadecanoyl-DL-homoserine lactone

Product Code:
 
CDX-H0202
Product Group:
 
Other Biochemicals
Supplier:
 
Chemodex
Regulatory Status:
 
RUO
Shipping:
 
AMBIENT
Storage:
 
-20°C
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Chemical Structure
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Chemical Structure

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CDX-H0202-M01010 mg£72.00
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CDX-H0202-M05050 mg£194.00
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Further Information

Alternate Names/Synonyms:
C16-HSL; N-Palmitoyl-DL-homoserine
Appearance:
White solid.
CAS:
98206-81-6
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light and moisture.
InChi:
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18-16-17-24-20(18)23/h18H,2-17H2,1H3,(H,21,22)
InChiKey:
QJIXVOQAEZMUIH-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 98206-81-6. Formula: C20H37NO3. MW: 339.5. Synthetic. N-Hexadecanoyl-DL-homoserine lactone (C16-HSL) 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. C16-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. C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells. 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:
MFCD31010412
Molecular Formula:
C20H37NO3
Molecular Weight:
339.5
Package Type:
Vial
Product Description:
N-Hexadecanoyl-DL-homoserine lactone (C16-HSL) 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. C16-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. C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells. 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% (GC)
SMILES:
CCCCCCCCCCCCCCCC(=O)NC1CCOC1=O
Solubility Chemicals:
Soluble in chloroform.
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) A.L. Schaefer, et al.; J. Bacteriol. 184, 6515 (2002) | (2) M.M. Marketon, et al.; J. Bacteriol. 184, 5686 (2002) | (3) M. Teplitski, et al.; Arch. Microbiol. 180, 494 (2003) | (4) I. Llamas, et al.; Appl. Enviro. Microbiol. 70, 3715 (2004) | (5) M. Gao, et al.; J. Bacteriol. 187, 7931 (2005) | (6) G.D. Geske, et al.; ChemBioChem 9, 389 (2008)