N-(3-Oxododecanoyl)-L-homoserine lactone
| Code | Size | Price |
|---|
| CDX-O0031-M010 | 10 mg | £72.00 |
Quantity:
| CDX-O0031-M020 | 20 mg | £121.00 |
Quantity:
| CDX-O0031-M100 | 100 mg | £291.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20 °C
Documents
Further Information
Alternate Names/Synonyms:
3-oxo-C12-HSL; 3OC12HSL; 3-Oxo-N-[(3S)-2-oxotetrahydro-3-furanyl]dodecanamide; N-(3-Oxododecanoyl) homoserine lactone; n-(3-Oxododecanoyl) L-homoserine lactone
Appearance:
White powder.
CAS:
168982-69-2
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light and moisture.
Hazards:
H302
InChi:
InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1
InChiKey:
PHSRRHGYXQCRPU-AWEZNQCLSA-N
Long Description:
Chemical. CAS: 168982-69-2. Formula: C16H27NO4. MW: 297.39. Synthetic. Quorum sensing agent.
MDL:
MFCD08275140
Molecular Formula:
C16H27NO4
Molecular Weight:
297.39
Package Type:
Vial
Precautions:
P264, P270, P301, P312, P330
Product Description:
Quorum sensing agent. N-(3-Oxododecanoyl)-L-homoserine lactone (3-oxo-C12-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. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention and formation of biofilms. 3-oxo-C12-HSL is one of the AHLs frequently identified in extracts of respiratory secretions from cystic fibrosis patients infected with P. aeruginosa and/or strains of the B. cepacia complex. 3-oxo-C12-HSL activates the transcription factors NF-kappaB and AP-2 to induce interleukin-8 production in human lung fibroblasts and epithelial cells, possibly contributing to the neutrophil infiltration and inflammation found in P. aeruginosa infections.
Purity:
>98% (NMR)
Signal word:
Warning
SMILES:
CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
Solubility Chemicals:
Soluble in DMSO (20mg/ml), DMF (20mg/ml) or 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) R.S. Smith, et al.; J. Immunol. 167, 366 (2001) | (2) E.A. Yates, et al.; Infect. Immun. 70, 5635 (2002) |(3) C.E. Chambers, et al.; FEMS Microbiol. Lett. 244, 297 (2005) | (4) G. Nakagami, et al.; FEMS Immunol. Med. Microbiol. 62, 157 (2011) | (5) V.K. Yadav, et al.; Int. J. Med. Microbiol. 308, 858 (2018)
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