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
- Molecular Weight:
- 199.25
- MDL Number:
- MFCD12912260
- MOL File:
- 147852-83-3.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| InChI | 1S/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)/t8-/m0/s1 |
| InChIKey | ZJFKKPDLNLCPNP-QMMMGPOBSA-N |
| SMILES | O=C1OCC[C@@H]1NC(CCCCC)=O |
| UNSPSC Code | 12352211 |
| NACRES | NA.28 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H335 |
| Precautionary statements | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
| WGK Germany | 3 |
| Storage Class | 11 - Combustible Solids |
N-hexanoyl-L-homoserine lactone price More Price(26)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 56395 | N-Hexanoyl-L-homoserine lactone ≥96% (HPLC) | 147852-83-3 | 10mg | $240 | 2026-04-30 | Buy |
| Sigma-Aldrich | 56395 | N-Hexanoyl-L-homoserine lactone ≥96% (HPLC) | 147852-83-3 | 50mg | $938 | 2026-04-30 | Buy |
| TCI Chemical | H1901 | N-Hexanoyl-L-homoserine Lactone | 147852-83-3 | 50MG | $175 | 2026-04-30 | Buy |
| Cayman Chemical | 10007896 | N-hexanoyl-L-Homoserine lactone ≥95% | 147852-83-3 | 5mg | $36 | 2026-04-30 | Buy |
| Cayman Chemical | 10007896 | N-hexanoyl-L-Homoserine lactone ≥95% | 147852-83-3 | 10mg | $53 | 2026-04-30 | Buy |
N-hexanoyl-L-homoserine lactone Chemical Properties, Uses, 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-
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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Adamas Reagent, Ltd. | 400-6009262 15618770481 | yhx@titansci.com | China | 14098 | 59 |
| Xiamen Dano Pharmaceutical Co., LTD(China) | 0592-6266840 15750707980; | chemdano@126.com | China | 411 | 57 |
| Shanghai Leto Pharmatech Co.,Ltd. | 86-021-5821 5861; 18016401466 | sales@letopharm.com | China | 235 | 58 |
| Bide Pharmatech Ltd. | 400-164-7117 18317119277 | product02@bidepharm.com | China | 40000 | 60 |
| Quality Control Solutions Ltd. | 0755-66853366 13670046396 | orders@qcsrm.com | China | 18188 | 56 |
| Shanghai Macklin Biochemical Co.,Ltd. | 15221275939 15221275939 | shenlinxing@macklin.cn | China | 15775 | 55 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9799 | 58 |
| Shanghai YuanYe Biotechnology Co., Ltd. | 15026964105 | 2881489226@qq.com | China | 89667 | 60 |
| Cangzhou Enke Pharma-tech Co., Ltd. | 0317-5296180 15533709196 | enkepharma@126.com | China | 2495 | 55 |
View Latest Price from N-hexanoyl-L-homoserine lactone manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-05-11 | N-hexanoyl-L-Homoserine lactone
147852-83-3
|
$31.00-106.00 | 99.09% | 10g | TargetMol Chemicals Inc. |
-
- N-hexanoyl-L-Homoserine lactone
147852-83-3
- $31.00-106.00
- 99.09%
- TargetMol Chemicals Inc.
