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
Available from stock
N-Dodecanoyl-L-homoserine lactone
- SKU
- D0335
Category: Quorum Sensing
- Synonyms
- N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide , dDHL , C12-HSL
- 137173-46-7
- CAS-Number
- C16H29NO3
- Molecular Formula
- 283.4
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- 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
- Description
- 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.
- Smiles
- CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
- InChi Key
- WILLZMOKUUPJSL-AWEZNQCLSA-N
- 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
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.
Additional information
| Synonyms | N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide, dDHL, C12-HSL |
|---|---|
| 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 |
