Specifications
- Purity
- ≥97% (GC)
- Identity
- 1H-NMR
- Appearance
- White solid
Properties
- Solvents
- chloroform
Available from stock
N-Dodecanoyl-DL-homoserine lactone
- SKU
- D0339
Category: Quorum Sensing
- Synonyms
- C12-HSL , N-(2-Oxotetrahydro-3-furanyl)dodecanamide , N-Lauroyl-DL-homoserine lactone
- 18627-38-8
- CAS-Number
- C16H29NO3
- Molecular Formula
- 283.4
- Molecular Weight
- Short Term Storage
- +4°C
- Use / Stability
- Stable for at least 2 years after receipt when stored at +4°C.
- Handling Advice
- Protect from light and moisture.
- Long Term Storage
- +4°C
- Shipping
- AMBIENT
- Transportation
- Not dangerous goods
- Description
- N-Dodecanoyl-DL-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 also was shown to induce cell death by apoptosis.
- 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)
- References
- (1) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994) , (2) K.H. McClean, et al.: Microbiol. 143, 3703 (1997) , (3) M.K. Parsek, et al.: PNAS 143, 3703 (1997) , (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000) , (5) G.D. Geske: JACS 127, 12762 (2005) , (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) , (9) L.R. Swem, et al.: Molecul. Cell 35, 143 (2009) , (10) J.T. Hodgkinson: Tetrahedron Lett. 52, 3291 (2011) , (11) D.G. Deryabina, et al.: Microbiol 82, 133 (2013)
- InChi Key
- WILLZMOKUUPJSL-UHFFFAOYSA-N
- Smiles
- CCCCCCCCCCCC(=O)NC1CCOC1=O
N-Dodecanoyl-DL-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 also was shown to induce cell death by apoptosis.
Additional information
| Synonyms | C12-HSL, N-(2-Oxotetrahydro-3-furanyl)dodecanamide, N-Lauroyl-DL-homoserine lactone |
|---|---|
| Purity | ≥97% (GC) |
| Appearance | White solid |
| CAS-Number | 18627-38-8 |
| Molecular Formula | C16H29NO3 |
| Molecular Weight | 283.4 |
| Identity | 1H-NMR |
| Solvents | chloroform |
| Smiles | CCCCCCCCCCCC(=O)NC1CCOC1=O |
| InChi Key | WILLZMOKUUPJSL-UHFFFAOYSA-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. |
| Transportation | Not dangerous goods |
| References | (1) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994), (2) K.H. McClean, et al.: Microbiol. 143, 3703 (1997), (3) M.K. Parsek, et al.: PNAS 143, 3703 (1997), (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000), (5) G.D. Geske: JACS 127, 12762 (2005), (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), (9) L.R. Swem, et al.: Molecul. Cell 35, 143 (2009), (10) J.T. Hodgkinson: Tetrahedron Lett. 52, 3291 (2011), (11) D.G. Deryabina, et al.: Microbiol 82, 133 (2013) |
| 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) |
| Quantity | 10 mg, 50 mg, Bulk |
