Specifications
- Purity
- ≥98% (NMR)
- Appearance
- White powder
- Identity
- 1H-NMR
Properties
- Solvents
- DMSO, dimethylformamide (approx. 30 mg/ml)
- Optical Activity
- [α]/D -25±5°, c = 0.2 in methanol
Category: Quorum Sensing
N-Dodecanoyl-L-homoserine lactone (C12-HSL) is a small diffusible signalling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. In addition to regulating bacterial functions, C12-HSL activates NF-kappaB in RAW 264.7 macrophages, increasing the expression of TNF-alpha, interleukin-1beta (IL-1beta) and IL-8, while other lactones do not. In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone, which is produced at different times in biofilm development and has different cellular effects.
Synonyms | N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide, dDHL, C12-HSL |
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Purity | ≥98% (NMR) |
Appearance | White powder |
CAS-Number | 137173-46-7 |
Molecular Formula | C16H29NO3 |
Molecular Weight | 283.4 |
Identity | 1H-NMR |
Solvents | DMSO, dimethylformamide (approx. 30 mg/ml) |
Optical Activity | [α]/D -25±5°, c = 0.2 in methanol |
Smiles | CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O |
InChi Key | WILLZMOKUUPJSL-AWEZNQCLSA-N |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | +4°C |
Handling Advice | Protect from light and moisture. |
Use / Stability | Stable for at least 2 years after receipt when stored at +4°C. |
Hazard statements | H413 |
Transportation | Not dangerous goods |
References | (1) G.D. Geske: JACS 127, 12762 (2005), (2) J.T. Hodgkinson: Tetrahedron Lett. 52, 3291 (2011), (3) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994), (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000), (5) K.H. McClean, et al.: Microbiol. 143, 3703 (1997), (6) K. Gomi, et al.: Infect. Immun. 74, 7029 (2006), (7) S. Kristiansen, et al.: APMIS 116, 361 (2008), (8) Y. Huang, et al.: ISME 1, (2008) |
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)/t14-/m0/s1 |
Quantity | 5 mg, 50 mg, Bulk |