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

SKU: O0060

Category: Quorum Sensing

Synonyms: 3-oxo-C14-HSL , 3OC14-HSL , N-3-oxo-Myristoyl-L-Homoserine lactone; 177158-19-9
CAS-Number: C₁₈H₃₁NO₄
Molecular Formula: 325.4
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 -20°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: -20°C
Shipping: AMBIENT

Transportation: Not dangerous goods

Description: N-(3-Oxotetradecanoyl)-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. It appears later than shorter acyl chain AHLs in developing biofilms and like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn inhibits biofilm formation.
InChi: InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1
References: (1) A. Kuo, et al.: J. Bacteriol. 176, 7558 (1994) , (2) A.L. Schaefer, et al.: J. Bacteriol. 178, 2897 (1996) , (3) K.H. McClean, et. al.: Microbiol. 143, 3703 (1997) , (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000) , (5) S.R. Chhabra, et al.: J. Med. Chem. 46, 97 (2003) , (6) G.D. Geske: JACS 127, 12762 (2005) , (7) J.F. Dubern, et al.: J. Bacteriol. 188, 2898 (2006) , (8) F.W. Bartels, et al.: Biophys. J. 92, 4391 (2007) , (9) A.M. Pomini & A.J. Marsaioli: J. Nat. Prod. 71, 1032 (2008) , (10) M. Wahjudi, et al.: Microbiol 157, 2042 (2011) , (11) B.M. Davis, et al.: Biophy. J. 101, 245 (2011) , (12) C.H. Tan, et al.: ISME J. 8, 1186 (2014) , (13) K.-G. Chan, et al.: Sci. World J. 2014, ID891041 (2014)
InChi Key: YQFJJDSGBAAUPW-INIZCTEOSA-N
Smiles: [H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCCCC

N-(3-Oxotetradecanoyl)-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. It appears later than shorter acyl chain AHLs in developing biofilms and like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn inhibits biofilm formation.

SKU: O0060 Category: Quorum Sensing

Additional information

Additional information

Synonyms	3-oxo-C14-HSL, 3OC14-HSL, N-3-oxo-Myristoyl-L-Homoserine lactone
Purity	≥97% (GC)
Appearance	White solid
CAS-Number	177158-19-9
Molecular Formula	C18H31NO4
Molecular Weight	325.4
Identity	1H-NMR
Solvents	chloroform
Smiles	[H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCCCC
InChi Key	YQFJJDSGBAAUPW-INIZCTEOSA-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. Kuo, et al.: J. Bacteriol. 176, 7558 (1994), (2) A.L. Schaefer, et al.: J. Bacteriol. 178, 2897 (1996), (3) K.H. McClean, et. al.: Microbiol. 143, 3703 (1997), (4) J.K. Lithgow, et al.: Mol. Microbiol. 37, 81 (2000), (5) S.R. Chhabra, et al.: J. Med. Chem. 46, 97 (2003), (6) G.D. Geske: JACS 127, 12762 (2005), (7) J.F. Dubern, et al.: J. Bacteriol. 188, 2898 (2006), (8) F.W. Bartels, et al.: Biophys. J. 92, 4391 (2007), (9) A.M. Pomini & A.J. Marsaioli: J. Nat. Prod. 71, 1032 (2008), (10) M. Wahjudi, et al.: Microbiol 157, 2042 (2011), (11) B.M. Davis, et al.: Biophy. J. 101, 245 (2011), (12) C.H. Tan, et al.: ISME J. 8, 1186 (2014), (13) K.-G. Chan, et al.: Sci. World J. 2014, ID891041 (2014)
InChi	InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1
Quantity	10 mg, 50 mg, Bulk