ChemicalBook > CAS DataBase List > N-hexanoyl-L-homoserine lactone

N-hexanoyl-L-homoserine lactone

Product Name: N-hexanoyl-L-homoserine lactone
CAS No.: 147852-83-3
Chemical Name: N-hexanoyl-L-homoserine lactone
Synonyms: C6-HSL;C6HSL,HHL;Hexanoyl-L-hoMoserine lactone;N-hexanoyl-L-homoserine lactone;N-[(3S)-2-oxooxolan-3-yl]hexanamide;C6-HSL, N-Hexanoyl-L-hoMoserine lactone;N-Hexanoyl-L-homoserine lactone(C6-HSL);(S)-N-(2-Oxotetrahydrofuran-3-yl)hexanamide;N-Hexanoyl-L-homoserine lactone, ≥96% (HPLC);N-[(3S)-Tetrahydro-2-oxo-3-furanyl]hexanamide
CBNumber: CB41312724
Molecular Formula: C10H17NO3
Formula Weight: 199.25
MOL File: 147852-83-3.mol

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N-hexanoyl-L-homoserine lactone Property

Melting point:: 132-134 °C(Solv: dichloromethane (75-09-2))
Boiling point:: 434.0±34.0 °C(Predicted)
Density: 1.08±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: DMF: 30 mg/ml; DMSO: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
form: A crystalline solid
pka: 15.03±0.20(Predicted)
color: White to light yellow
optical activity: [α]/D -32±3°, c = 0.2 in methanol
BRN: 8143287

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 56395
Product name: N-Hexanoyl-L-homoserine lactone
Purity: ≥96% (HPLC)
Packaging: 10mg
Price: $227
Updated: 2025/07/31

Sigma-Aldrich

Product number: 56395
Product name: N-Hexanoyl-L-homoserine lactone
Purity: ≥96% (HPLC)
Packaging: 50mg
Price: $888
Updated: 2025/07/31

TCI Chemical

Product number: H1901
Product name: N-Hexanoyl-L-homoserine Lactone
Packaging: 50MG
Price: $246
Updated: 2025/07/31

Cayman Chemical

Product number: 10007896
Product name: N-hexanoyl-L-Homoserine lactone
Purity: ≥95%
Packaging: 5mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 10007896
Product name: N-hexanoyl-L-Homoserine lactone
Purity: ≥95%
Packaging: 10mg
Price: $48
Updated: 2024/03/01

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N-hexanoyl-L-homoserine lactone Chemical Properties,Usage,Production

Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-hexanoyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and affecting cellular metabolism. The diverse applications of this molecule include regulation of virulence in general and in cystic fibrosis, infection prevention, slime and biofilm reduction in commercial agriculture and aquaculture industries, food spoilage prevention, and septicemia in fish.

Uses

Hexanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Rhizobium leguminosarum. Hexanoyl-L-homoserine lactone and other acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorter chains displaying opposing actions to the longer chains.

Definition

ChEBI: N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide is a N-acyl-amino acid.

General Description

N-Hexanoyl-L-homoserine lactone is produced and utilized by various Gram-negative bacteria as a quorum sensing (QS) signal molecule.

Biochem/physiol Actions

N-Hexanoyl-L-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.

References

[1] TOMOHIRO MOROHOSHI . Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen Edwardsiella tarda[J]. Journal of bioscience and bioengineering, 2004, 98 4: Pages 274-281. DOI: 10.1016/s1389-1723(04)00281-6
[2] RICKY L ULRICH. Mutational analysis and biochemical characterization of the Burkholderia thailandensis DW503 quorum-sensing network.[J]. Journal of Bacteriology, 2004, 186 13: 4350-4360. DOI: 10.1128/jb.186.13.4350-4360.2004
[3] LIAN-HUI WANG. Specificity and enzyme kinetics of the quorum-quenching N-Acyl homoserine lactone lactonase (AHL-lactonase).[J]. The Journal of Biological Chemistry, 2004, 279 14: 13645-13651. DOI: 10.1074/jbc.m311194200
[4] EDWIN A YATES. N-acylhomoserine lactones undergo lactonolysis in a pH-, temperature-, and acyl chain length-dependent manner during growth of Yersinia pseudotuberculosis and Pseudomonas aeruginosa.[J]. Infection and Immunity, 2002, 70 10: 5635-5646. DOI: 10.1128/iai.70.10.5635-5646.2002
[5] ZHAO-QING LUO S K F Shengchang Su. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: kinetics and consequences.[J]. Journal of Bacteriology, 2003, 185 19: 5665-5672. DOI: 10.1128/jb.185.19.5665-5672.2003
[6] ALLAN B CHRISTENSEN. Quorum-sensing-directed protein expression in Serratia proteamaculans B5a.[J]. Microbiology-Sgm, 2003, 149 Pt 2: 471-483. DOI: 10.1099/mic.0.25575-0
[7] CATHERINE E. CHAMBERS. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients[J]. Fems Microbiology Letters, 2006, 244 2: 297-304. DOI: 10.1016/j.femsle.2005.01.055

N-hexanoyl-L-homoserine lactone Preparation Products And Raw materials

Raw materials

Preparation Products

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147852-83-3