N-(3-Oxohexanoyl)-L-homoserine lactone

SKU: O0057

Category: Quorum Sensing

Synonyms: 3-oxo-C6-HSL , N-(β-Ketocaproyl)-L-homoserine lactone; 143537-62-6
CAS-Number: C₁₀H₁₅NO₄
Molecular Formula: 213.2
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

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

Properties

Solvents: chloroform

Downloads

Safety Data Sheet: CDX O0057 MSDS.pdf

Short Term Storage: +4°C
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: -20°C
Shipping: AMBIENT

Transportation: Not dangerous goods

Description: N-(3-Oxohexanoyl)-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. At increased populations of bacteria, localized higher concentrations of 3OC6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence. Numerous other species of bacteria also employ 3OC6-HSL in cell-to-cell communication. An autoinducer of P. fischeri luciferase and a specfic genetic regulator that is unrelated to at least one of the enzyme systems that it induces. It acts after excretion and accumulation in the extracellular medium.
InChi: InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1
References: (1) A. Eberhard, et al.: Arch. Microbiol. 146, 35 (1986) , (2) N.J. Bainton, et al.: Biochem. J. 288, 997 (1992) , (3) P. Williams, et al.: FEMS Microbiol. Lett. 100, 161 (1992) , (4) R.H. Gomer: Curr. Biol. 4, 734 (1994) , (5) A. Chatterjee, et al.: Appl. Environ.Microbiol. 61, 1959 (1995) , (6) Y.H. Dong, et al.: Nature 411, 813 (2001) , (7) G.D. Geske, et al.: Bioorg. Med. Chem. Lett. 18, 5978 (2008) , (8) R.L. Frey, et al.: Environ. Sci. Tech. 44, 7465 (2010)
InChi Key: YRYOXRMDHALAFL-QMMMGPOBSA-N
Smiles: [H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCC

N-(3-Oxohexanoyl)-L-homoserine lactone is a small diffusible signaling molecule and is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) are involved in quorum sensing, controlling gene expression, and cellular metabolism. The diverse applications of this kind of molecule include regulation of virulence in general, infection prevention, and formation of biofilms. At increased populations of bacteria, localized higher concentrations of 3OC6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence. Numerous other species of bacteria also employ 3OC6-HSL in cell-to-cell communication. An autoinducer of P. fischeri luciferase and a specfic genetic regulator that is unrelated to at least one of the enzyme systems that it induces. It acts after excretion and accumulation in the extracellular medium.

SKU: O0057 Category: Quorum Sensing

Additional information

Additional information

Synonyms	3-oxo-C6-HSL, N-(β-Ketocaproyl)-L-homoserine lactone
Purity	≥97% (GC)
Appearance	White solid
CAS-Number	143537-62-6
Molecular Formula	C10H15NO4
Molecular Weight	213.2
Identity	1H-NMR
Solvents	chloroform
Smiles	[H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCC
InChi Key	YRYOXRMDHALAFL-QMMMGPOBSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Transportation	Not dangerous goods
References	(1) A. Eberhard, et al.: Arch. Microbiol. 146, 35 (1986), (2) N.J. Bainton, et al.: Biochem. J. 288, 997 (1992), (3) P. Williams, et al.: FEMS Microbiol. Lett. 100, 161 (1992), (4) R.H. Gomer: Curr. Biol. 4, 734 (1994), (5) A. Chatterjee, et al.: Appl. Environ.Microbiol. 61, 1959 (1995), (6) Y.H. Dong, et al.: Nature 411, 813 (2001), (7) G.D. Geske, et al.: Bioorg. Med. Chem. Lett. 18, 5978 (2008), (8) R.L. Frey, et al.: Environ. Sci. Tech. 44, 7465 (2010)
InChi	InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1
Quantity	10 mg, 50 mg, Bulk