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N-Tetradecanoyl-DL-homoserine lactone - ≥97.0% (HPLC), high purity , CAS No.98206-80-5

  • ≥97%(HPLC)
Item Number
N464450
Grouped product items
SKUSizeAvailabilityPrice Qty
N464450-25mg
25mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$630.90

Basic Description

Synonyms98206-80-5|N-(2-oxooxolan-3-yl)tetradecanamide|N-(2-Oxotetrahydrofuran-3-yl)tetradecanamide|Tetradecanamide, N-(tetrahydro-2-oxo-3-furanyl)-|C14-homoserine lactone|SCHEMBL15904708|DTXSID00404029|CHEBI:181696|ZQAYHOXXVBVXPZ-UHFFFAOYSA-N|Homoserine lactone,
Specifications & Purity≥97.0% (HPLC)
Storage TempStore at 2-8°C
Shipped InWet ice
Product Description

Description

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

Names and Identifiers

IUPAC Name N-(2-oxooxolan-3-yl)tetradecanamide
INCHI InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)
InChi Key ZQAYHOXXVBVXPZ-UHFFFAOYSA-N
Canonical SMILES CCCCCCCCCCCCCC(=O)NC1CCOC1=O
Isomeric SMILES CCCCCCCCCCCCCC(=O)NC1CCOC1=O
PubChem CID 4534674
Molecular Weight 311.46
Beilstein 1649579

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Flash Point(°F)Not applicable
Flash Point(°C)Not applicable

Safety and Hazards(GHS)

RIDADR NONH for all modes of transport

Related Documents

References

1. K H McClean,M K Winson,L Fish,A Taylor,S R Chhabra,M Camara,M Daykin,J H Lamb,S Swift,B W Bycroft,G S Stewart,P Williams.  (1998-01-09)  Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones..  Microbiology (Reading, England),  143   (( Pt 12)): (3703-3711).  [PMID:9421896]
2. 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]
3. 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]
4. Feng-Sheng Wang,Ching-Jen Wang,Yeung-Jen Chen,Per-Rong Chang,Yu-Ting Huang,Yi-Chih Sun,Hueng-Chen Huang,Ya-Ju Yang,Kuender D Yang.  (2003-12-19)  Ras induction of superoxide activates ERK-dependent angiogenic transcription factor HIF-1alpha and VEGF-A expression in shock wave-stimulated osteoblasts..  The Journal of biological chemistry,  279  ((11)): (10331-10337).  [PMID:14681237]
5. 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]
6. 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]
7. 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]
8. 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]
9. 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]
10. Francisco Pérez-Montaño,Beatriz Guasch-Vidal,Sergio González-Barroso,Francisco Javier López-Baena,Teresa Cubo,Francisco Javier Ollero,Antonio M Gil-Serrano,Miguel Ángel Rodríguez-Carvajal,Ramón A Bellogín,M Rosario Espuny.  (2011-05-24)  Nodulation-gene-inducing flavonoids increase overall production of autoinducers and expression of N-acyl homoserine lactone synthesis genes in rhizobia..  Research in microbiology,  162  ((7)): (715-723).  [PMID:21600980]
11. 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]
12. 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]
13. Haijun Ma,Xuezhu Wang,Yan Zhang,Haidong Hu,Hongqiang Ren,Jinju Geng,Lili Ding.  (2017-09-26)  The diversity, distribution and function of N-acyl-homoserine lactone (AHL) in industrial anaerobic granular sludge..  Bioresource technology,  247  (116-124).  [PMID:28946084]
14. Firoj Ahmed,Takashi Ohtsuki,Wataru Aida,Masami Ishibashi.  (2008-10-14)  Tyrosine derivatives isolated from Streptomyces sp. IFM 10937 in a screening program for TRAIL-resistance-overcoming activity..  Journal of natural products,  71  ((11)): (1963-1966).  [PMID:18847278]

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