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

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (NMR)
Identity: 1H-NMR
Appearance: White powder

Properties

Optical Activity: [α]/D -25±5°, c = 0.2 in methanol
Solvents: DMSO, dimethylformamide (approx. 30 mg/ml)

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
Hazard statements: H413

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.
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
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 Key: WILLZMOKUUPJSL-AWEZNQCLSA-N
Smiles: CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O

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.

SKU: D0335 Category: Quorum Sensing

Additional information

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