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

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥97% (GC)
Identity: 1H-NMR
Appearance: White solid

Properties

Solvents: chloroform

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.

SKU: D0339 Category: Quorum Sensing

Additional information

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