Available from stock

N-Hexadecanoyl-DL-homoserine lactone

SKU: H0202

Category: Quorum Sensing

Synonyms: C16-HSL , N-Palmitoyl-DL-homoserine; 98206-81-6
CAS-Number: C₂₀H₃₇NO₃
Molecular Formula: 339.5
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

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

Properties

Solvents: chloroform

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

Description: N-Hexadecanoyl-DL-homoserine lactone (C16-HSL) 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. C16-HSL is a lipophilic, long acyl side-chain bearing AHL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes. C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells. It tends to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by extracellular outer membrane vesicles.
Smiles: CCCCCCCCCCCCCCCC(=O)NC1CCOC1=O
InChi Key: QJIXVOQAEZMUIH-UHFFFAOYSA-N
References: (1) A.L. Schaefer, et al.: J. Bacteriol. 184, 6515 (2002) , (2) M.M. Marketon, et al.: J. Bacteriol. 184, 5686 (2002) , (3) M. Teplitski, et al.: Arch. Microbiol. 180, 494 (2003) , (4) I. Llamas, et al.: Appl. Enviro. Microbiol. 70, 3715 (2004) , (5) M. Gao, et al.: J. Bacteriol. 187, 7931 (2005) , (6) G.D. Geske, et al.: ChemBioChem 9, 389 (2008)
InChi: InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18-16-17-24-20(18)23/h18H,2-17H2,1H3,(H,21,22)

N-Hexadecanoyl-DL-homoserine lactone (C16-HSL) 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. C16-HSL is a lipophilic, long acyl side-chain bearing AHL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes. C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells. It tends to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by extracellular outer membrane vesicles.

SKU: H0202 Category: Quorum Sensing

Additional information

Additional information

Synonyms	C16-HSL, N-Palmitoyl-DL-homoserine
Purity	≥97% (GC)
Appearance	White solid
CAS-Number	98206-81-6
Molecular Formula	C20H37NO3
Molecular Weight	339.5
Identity	1H-NMR
Solvents	chloroform
Smiles	CCCCCCCCCCCCCCCC(=O)NC1CCOC1=O
InChi Key	QJIXVOQAEZMUIH-UHFFFAOYSA-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.L. Schaefer, et al.: J. Bacteriol. 184, 6515 (2002), (2) M.M. Marketon, et al.: J. Bacteriol. 184, 5686 (2002), (3) M. Teplitski, et al.: Arch. Microbiol. 180, 494 (2003), (4) I. Llamas, et al.: Appl. Enviro. Microbiol. 70, 3715 (2004), (5) M. Gao, et al.: J. Bacteriol. 187, 7931 (2005), (6) G.D. Geske, et al.: ChemBioChem 9, 389 (2008)
InChi	InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18-16-17-24-20(18)23/h18H,2-17H2,1H3,(H,21,22)
Quantity	10 mg, 50 mg, Bulk