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N-Dodecanoyl-DL-homoserine lactone - ≥97.0% (HPLC), high purity , CAS No.18627-38-8

  • ≥97%
Item Number
N464439
Grouped product items
SKUSizeAvailabilityPrice Qty
N464439-5mg
5mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$69.90
N464439-10mg
10mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$112.90
N464439-25mg
25mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$224.90
N464439-50mg
50mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$359.90
N464439-100mg
100mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$579.90
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Amino Acid Derivatives

Basic Description

SynonymsN-Dodecanoyl-DL-homoserine lactone|18627-38-8|N-(2-OXOOXOLAN-3-YL)DODECANAMIDE|N-(2-Oxotetrahydrofuran-3-yl)dodecanamide|C12-HSL|N-Lauroyl-DL-homoserine lactone|C12-homoserine lactone|SCHEMBL3738642|CHEBI:182085|WILLZMOKUUPJSL-UHFFFAOYSA-N|DTXSID501346599
Specifications & Purity≥97%
Storage TempStore at 2-8°C
Shipped InWet ice
Product Description

Description

Application test: Induces violacein expression in aChromobacterium violaceummutant usually not able to produce homoserine lactones.

Names and Identifiers

IUPAC Name N-(2-oxooxolan-3-yl)dodecanamide
INCHI InChI=1S/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)
InChi Key WILLZMOKUUPJSL-UHFFFAOYSA-N
Canonical SMILES CCCCCCCCCCCC(=O)NC1CCOC1=O
Isomeric SMILES CCCCCCCCCCCC(=O)NC1CCOC1=O
PubChem CID 11565426
Molecular Weight 283.41

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Flash Point(°F)Not applicable
Flash Point(°C)Not applicable
Melt Point(°C)114-117℃

Safety and Hazards(GHS)

Signal Warning
Hazard Statements

H315:Causes skin irritation

H319:Causes serious eye irritation

H335:May cause respiratory irritation

H302:Harmful if swallowed

Precautionary Statements

P261:Avoid breathing dust/fume/gas/mist/vapors/spray.

P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing.

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352:IF ON SKIN: wash with plenty of water.

P301+P312:IF SWALLOWED: call a POISON CENTER/doctor/... IF you feel unwell.

RIDADR NONH for all modes of transport

Related Documents

 SDS

 Specification Sheet

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References

1. S Swift,M J Lynch,L Fish,D F Kirke,J M Tomás,G S Stewart,P Williams.  (1999-09-25)  Quorum sensing-dependent regulation and blockade of exoprotease production in Aeromonas hydrophila..  Infection and immunity,  67  ((10)): (5192-5199).  [PMID:10496895]
2. L Eberl.  (2000-05-04)  N-acyl homoserinelactone-mediated gene regulation in gram-negative bacteria..  Systematic and applied microbiology,  22  ((4)): (493-506).  [PMID:10794136]
3. Ricky L Ulrich,David Deshazer,Ernst E Brueggemann,Harry B Hines,Petra C Oyston,Jeffrey A Jeddeloh.  (2004-10-22)  Role of quorum sensing in the pathogenicity of Burkholderia pseudomallei..  Journal of medical microbiology,  53  ((Pt 11)): (1053-1064).  [PMID:15496380]
4. Leo Eberl.  (2006-02-24)  Quorum sensing in the genus Burkholderia..  International journal of medical microbiology : IJMM,  296  ((2-3)): (103-110).  [PMID:16490397]
5. Kazunori Gomi,Toshiaki Kikuchi,Yutaka Tokue,Shigeru Fujimura,Akiko Uehara,Haruhiko Takada,Akira Watanabe,Toshihiro Nukiwa.  (2006-09-20)  Mouse and human cell activation by N-dodecanoyl-DL-homoserine lactone, a Chromobacterium violaceum autoinducer..  Infection and immunity,  74  ((12)): (7029-7031).  [PMID:16982829]
6. Frank Wilco Bartels,Matthew McIntosh,Alexander Fuhrmann,Christoph Metzendorf,Patrik Plattner,Norbert Sewald,Dario Anselmetti,Robert Ros,Anke Becker.  (2007-03-27)  Effector-stimulated single molecule protein-DNA interactions of a quorum-sensing system in Sinorhizobium meliloti..  Biophysical journal,  92  ((12)): (4391-4400).  [PMID:17384071]
7. Selvaraj Poonguzhali,Munusamy Madhaiyan,Tongmin Sa.  (2007-12-07)  Production of acyl-homoserine lactone quorum-sensing signals is widespread in gram-negative Methylobacterium..  Journal of microbiology and biotechnology,  17  ((2)): (226-233).  [PMID:18051753]
8. Tomohiro Morohoshi,Masashi Kato,Katsumasa Fukamachi,Norihiro Kato,Tsukasa Ikeda.  (2008-01-08)  N-acylhomoserine lactone regulates violacein production in Chromobacterium violaceum type strain ATCC 12472..  FEMS microbiology letters,  279  ((1)): (124-130).  [PMID:18177311]
9. Robert Czajkowski,Sylwia Jafra.  (2009-03-17)  Quenching of acyl-homoserine lactone-dependent quorum sensing by enzymatic disruption of signal molecules..  Acta biochimica Polonica,  56  ((1)): (1-16).  [PMID:19287806]
10. Ping Kong,Brett M Tyler,Patricia A Richardson,Bobby W K Lee,Zhaohui S Zhou,Chuanxue Hong.  (2010-12-09)  Zoospore interspecific signaling promotes plant infection by Phytophthora..  BMC microbiology,  10  (313-313).  [PMID:21138563]
11. Jitesh A Soares,Brian M M Ahmer.  (2011-03-01)  Detection of acyl-homoserine lactones by Escherichia and Salmonella..  Current opinion in microbiology,  14  ((2)): (188-193).  [PMID:21353625]
12. Thommie Karlsson,Farah Musse,Karl-Eric Magnusson,Elena Vikström.  (2011-08-03)  N-Acylhomoserine lactones are potent neutrophil chemoattractants that act via calcium mobilization and actin remodeling..  Journal of leukocyte biology,  91  ((1)): (15-26).  [PMID:21807742]
13. Ali E McClean,Breck A Duerkop,E Peter Greenberg,Daniel A Kluepfel.  (2012-01-13)  AHL signals induce rubrifacine production in a bruI mutant of Brenneria rubrifaciens..  Phytopathology,  102  ((2)): (195-203).  [PMID:22236075]
14. Maria Pellegrini,Laure Willen,Mai Perroud,Dennis Krushinskie,Kathy Strauch,Hernan Cuervo,Eric S Day,Pascal Schneider,Timothy S Zheng.  (2013-02-27)  Structure of the extracellular domains of human and Xenopus Fn14: implications in the evolution of TWEAK and Fn14 interactions..  The FEBS journal,  280  ((8)): (1818-1829).  [PMID:23438059]
15. A A Purohit,J A Johansen,H Hansen,H-K S Leiros,A Kashulin,C Karlsen,A Smalås,P Haugen,N P Willassen.  (2013-06-04)  Presence of acyl-homoserine lactones in 57 members of the Vibrionaceae family..  Journal of applied microbiology,  115  ((3)): (835-847).  [PMID:23725044]
16. Felipe Alves de Almeida,Natan de Jesus Pimentel-Filho,Lanna Clícia Carrijo,Cláudia Braga Pereira Bento,Maria Cristina Baracat-Pereira,Uelinton Manoel Pinto,Leandro Licursi de Oliveira,Maria Cristina Dantas Vanetti.  (2016-12-06)  Acyl homoserine lactone changes the abundance of proteins and the levels of organic acids associated with stationary phase in Salmonella Enteritidis..  Microbial pathogenesis,  102  (148-159).  [PMID:27916690]
17. Miriam Khider,Hilde Hansen,Erik Hjerde,Jostein A Johansen,Nils Peder Willassen.  (2019-05-21)  Exploring the transcriptome of luxI- and ΔainS mutants and the impact of N-3-oxo-hexanoyl-L- and N-3-hydroxy-decanoyl-L-homoserine lactones on biofilm formation in Aliivibrio salmonicida..  PeerJ,  7  (e6845-e6845).  [PMID:31106062]
18. Shujuan Huang,Hui Zhang,Tze Chiang Albert Ng,Boyan Xu,Xueqing Shi,How Yong Ng.  (2020-04-16)  Analysis of N-Acy-L-homoserine lactones (AHLs) in wastewater treatment systems using SPE-LLE with LC-MS/MS..  Water research,  177  (115756-115756).  [PMID:32294590]
19. Maybelle Kho Go,Li Na Zhao,Bo Xue,Shreyas Supekar,Robert C Robinson,Hao Fan,Wen Shan Yew.  (2020-04-23)  Directed Computational Evolution of Quorum-Quenching Lactonases from the Amidohydrolase Superfamily..  Structure (London, England : 1993),  28  ((6)): (635-642).  [PMID:32320671]
20. Sophie Uzureau,Julien Lemaire,Edouard Delaive,Marc Dieu,Anthoula Gaigneaux,Martine Raes,Xavier De Bolle,Jean-Jacques Letesson.  (2010-04-15)  Global analysis of quorum sensing targets in the intracellular pathogen Brucella melitensis 16 M..  Journal of proteome research,  9  ((6)): (3200-3217).  [PMID:20387905]
21. Daniel Wynn,Nilesh Raut,Smita Joel,Patrizia Pasini,Sapna K Deo,Sylvia Daunert.  (2018-09-15)  Detection of bacterial contamination in food matrices by integration of quorum sensing in a paper-strip test..  The Analyst,  143  ((19)): (4774-4782).  [PMID:30215084]
22. Leonardo Luiz de Freitas,Fernanda Pereira da Silva,Kenner Morais Fernandes,Deisy Guimarães Carneiro,Leandro Licursi de Oliveira,Gustavo Ferreira Martins,Maria Cristina Dantas Vanetti.  (2021-01-15)  The virulence of Salmonella Enteritidis in Galleria mellonella is improved by N-dodecanoyl-homoserine lactone..  Microbial pathogenesis,  152  (104730-104730).  [PMID:33444697]

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