N-(3-Oxotetradecanoyl)-L-homoserine lactone

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Chemodex
Product Code: CDX-O0060
Product Group: Other Biochemicals
Supplier: Chemodex
CodeSizePrice
CDX-O0060-M01010 mg£72.00
Quantity:
CDX-O0060-M05050 mg£255.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
-20°C

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Chemical Structure
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Chemical Structure

Documents

Further Information

Alternate Names/Synonyms:
3-oxo-C14-HSL; 3OC14-HSL; N-3-oxo-Myristoyl-L-Homoserine lactone
Appearance:
White solid.
CAS:
177158-19-9
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light and moisture.
InChi:
InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1
InChiKey:
YQFJJDSGBAAUPW-INIZCTEOSA-N
Long Description:
Chemical. CAS: 177158-19-9. Formula: C18H31NO4. MW: 325.4. Synthetic. N-(3-Oxotetradecanoyl)-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. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. It appears later than shorter acyl chain AHLs in developing biofilms and like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn inhibits biofilm formation.
MDL:
MFCD12912433
Molecular Formula:
C18H31NO4
Molecular Weight:
325.4
Package Type:
Vial
Product Description:
N-(3-Oxotetradecanoyl)-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. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. It appears later than shorter acyl chain AHLs in developing biofilms and like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn inhibits biofilm formation.
Purity:
>97% (GC)
SMILES:
[H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCCCC
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. Kuo, et al.; J. Bacteriol. 176, 7558 (1994) | (2) A.L. Schaefer, et al.; J. Bacteriol. 178, 2897 (1996) | (3) K.H. McClean, et. al.; Microbiol. 143, 3703 (1997) | (4) J.K. Lithgow, et al.; Mol. Microbiol. 37, 81 (2000) | (5) S.R. Chhabra, et al.; J. Med. Chem. 46, 97 (2003) | (6) G.D. Geske; JACS 127, 12762 (2005) | (7) J.F. Dubern, et al.; J. Bacteriol. 188, 2898 (2006) | (8) F.W. Bartels, et al.; Biophys. J. 92, 4391 (2007) | (9) A.M. Pomini & A.J. Marsaioli; J. Nat. Prod. 71, 1032 (2008) | (10) M. Wahjudi, et al.; Microbiol 157, 2042 (2011) | (11) B.M. Davis, et al.; Biophy. J. 101, 245 (2011) | (12) C.H. Tan, et al.; ISME J. 8, 1186 (2014) | (13) K.-G. Chan, et al.; Sci. World J. 2014, ID891041 (2014)

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