N-Hexanoyl-L-homoserine lactone (C6-HSL) - ≥98% , CAS No.147852-83-3

CAS: 147852-83-3 Cat. No.: H275885 Molecular Weight: 199.25

GRADE & PURITY ≥98%

Synonyms

HY-133685 | AKOS030603082 | MFCD12912260 | HL6 | HMS3650K17 | N-Hexanoyl-L-homoserine lactone, >=96% (HPLC) | Q27461124 | C21197 | N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide | N-hexanoyl-L-Homoserine lactone | J-008418 | CHEBI:181934 | Hexanoyl-L-homose

Storage

Store at -20°C,Argon charged,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at +4°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

HY-133685 | AKOS030603082 | MFCD12912260 | HL6 | HMS3650K17 | N-Hexanoyl-L-homoserine lactone, >=96% (HPLC) | Q27461124 | C21197 | N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide | N-hexanoyl-L-Homoserine lactone | J-008418 | CHEBI:181934 | Hexanoyl-L-homose

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

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 Escherichia coli and salmonella, and are involved in quorum sensing and cell-to-ce

Storage

Store at -20°C, Argon charged, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

MODULATOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCC(=O)NC1CCOC1=O
• IUPAC Name: N-[(3S)-2-oxooxolan-3-yl]hexanamide
• InChIKey: ZJFKKPDLNLCPNP-QMMMGPOBSA-N
• 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
• Isomeric SMILES: CCCCCC(=O)N[C@H]1CCOC1=O
• Molecular Weight: 199.25
• Reaxy-Rn: 1640340
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1640340&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-acyl-alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids and derivatives
• Alternative Parents: Alpha amino acid esters Acyl-L-homoserine lactones N-acyl amines Gamma butyrolactones Oxolanes Secondary carboxylic acid amides Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Alpha-amino acid ester - N-acyl-alpha amino acid or derivatives - Acyl-homoserine lactone - Acyl-l-homoserine lactone - Fatty amide - Gamma butyrolactone - N-acyl-amine - Fatty acyl - Oxolane - Secondary carboxylic acid amide - Lactone - Carboxylic acid ester - Carboxamide group - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO
• Specific Rotation[α]: [α]/D -32±3°, c = 0.2 in methanol
• Molecular Weight: 199.250 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 199.121 Da
• Monoisotopic Mass: 199.121 Da
• Topological Polar Surface Area: 55.400 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 215.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zixuan Ou, Xindi Chen, Xinming Wu, Changren Zhou, Kaijie Zhang, Jingyang Luo, Fang Fang, Yinqiang Sun, Ming Li, Qian Feng.  (2023)  N-acyl homoserine lactone mediating initial adhesion of microalgal biofilm formation.  ENVIRONMENTAL RESEARCH,      [PMID:37331555] [10.1016/j.envres.2023.116446]

2. Xiaolei Liu, Bin Ji, Anjie Li.  (2023)  Enhancing biolipid production and self-flocculation of Chlorella vulgaris by extracellular polymeric substances from granular sludge with CO2 addition: Microscopic mechanism of microalgae-bacteria symbiosis.  WATER RESEARCH,      [PMID:37054610] [10.1016/j.watres.2023.119960]

3. Lei Liao, Bin Chen, Kaikai Deng, Qiang He, Guijiao Lin, Jinsong Guo, Peng Yan.  (2023)  Effect of the N-hexanoyl-L-homoserine Lactone on the Carbon Fixation Capacity of the Algae–Bacteria System.  International Journal of Environmental Research and Public Health,  20  (6): (5047).  [PMID:36981956] [10.3390/ijerph20065047]

4. Qian Feng, Laiwei Luo, Xindi Chen, Kaijie Zhang, Fang Fang, Zhaoxia Xue, Chao Li, Jiashun Cao, Jingyang Luo.  (2021)  Facilitating biofilm formation of Pseudomonas aeruginosa via exogenous N-Acy-L-homoserine lactones stimulation: Regulation on the bacterial motility, adhesive ability and metabolic activity.  BIORESOURCE TECHNOLOGY,      [PMID:34411944] [10.1016/j.biortech.2021.125727]

5. Qian-Jun Deng, Min Chen, Dong-Chu Chen, Chang-Ai Chen.  (2019)  Two Tetranuclear Butterfly-Shaped Co(II) Complexes: Structure, Mass Spectrometric, and Magnetism.  Crystals,  9  (9): (477).  [PMID:] [10.3390/cryst9090477]

6. Wang Xiaoshuo Wu Pengfei, Lu Siyuan Xu Pengpeng.  (2016)  Structure and Photocatalytic Property of a Novel Three-Dimensional Supramolecular Cu(ΙΙ) Coordination Polymer with pcu Topology Based on the Rigid Multifunctional Ligand.  Journal of Inorganic and Organometallic Polymers and Materials,  26  (5): (1101-1106).  [PMID:] [10.1007/s10904-016-0404-9]

7. Siyi Chen, Ziang Kong, Liwei Qiu, Han Wang, Qun Yan.  (2024)  Effects of different quorum sensing signal molecules on alleviation of ammonia inhibition during biomethanation.  ENVIRONMENTAL RESEARCH,      [PMID:39505134] [10.1016/j.envres.2024.120295]

8. Rourou Zhang, Zijing Wang, Guibai Li, Heng Liang, Bingsheng Liu, Geoffroy Lesage, Marc Heran, An Ding, Huu Hao Ngo.  (2024)  Quorum sensing on the activated performances of gravity-driven membrane (GDM) system at low temperatures: Ammonia removal and flux stabilization.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2024.130238]

9. Ai-Hua Li, Bao-Cai Zhang, Wen-Tao Li, Cong-Cong Tang, Ai-Juan Zhou, Yong-Xiang Ren, Zhihua Li, Wenzong Liu, Zhang-Wei He.  (2024)  Quorum-sensing molecules regulate biochar-assisted anaerobic digestion system for methane production: Single-stage vs. two-stage digestion.  RENEWABLE ENERGY,      [PMID:] [10.1016/j.renene.2024.121367]

10. Fenglin Zhang, Jinming Gu, Yibing Wang, Qing Qiu, Yue Yu, Xuejian Sun, Menghan Chang, Dandan Zhou, Hongliang Huo, Kejian Tian.  (2024)  Regulatory mechanism by which exogenous AHLs enhance the degradation of bisphenol A by Pseudomonas asiatica P1.  Environmental Technology & Innovation,      [PMID:] [10.1016/j.eti.2024.103963]

11. Ai-Hua Li, Bao-Cai Zhang, Zhang-Wei He, Cong-Cong Tang, Ai-Juan Zhou, Yong-Xiang Ren, Zhihua Li, Aijie Wang, Wenzong Liu.  (2024)  Roles of quorum-sensing molecules in methane production from anaerobic digestion aided by biochar.  JOURNAL OF ENVIRONMENTAL MANAGEMENT,      [PMID:39032259] [10.1016/j.jenvman.2024.121867]

12. Cheng Qu, Yuchuang Geng, Zhongxiang Ding, Yuzhu Li, Hao Jiang, Mengke Su, Honglin Liu.  (2024)  In Situ Spatiotemporal SERS Profiling of Bacterial Quorum Sensing by Hierarchical Hydrophobic Plasmonic Arrays in Agar Medium.  ANALYTICAL CHEMISTRY,      [PMID:38305857] [10.1021/acs.analchem.3c04299]

13. Bin-Di Mao, Kai-Yuan Li, Ashiwin Vadiveloo, Jun-Jie Gu, Feng Gao.  (2025)  Bacterial N-acyl-homoserine lactone enhances the degradation of sulfamethoxazole by microalgae and the associated metabolic regulatory mechanisms.  BIORESOURCE TECHNOLOGY,      [PMID:40188853] [10.1016/j.biortech.2025.132487]

14. Kejian Tian, Fenglin Zhang, Yibing Wang, Jinming Gu, Dandan Zhou, Fanxing Meng, Wenkang Mu, Pengfei Hao, Hongliang Huo, Fan Li.  (2025)  C6‑HSL Enhances BPA Tolerance in Pseudomonas asiatica: An Integrative Raman‑DIP and Transcriptomic Study.  Current Research in Microbial Sciences,      [PMID:41480484] [10.1016/j.crmicr.2025.100530]

15. Meng Yuan, Guotao Chen, Zhiqi Zhang, Jinghui Wang, Yan Zhao, Guanghong Xie, Yin Jiang, Yuan Ren.  (2026)  Yarrowia lipolytica extracellular metabolites induce microbial signaling and interactions to enhance chlorinated hydrocarbon degradation in soil.  Journal of Environmental Chemical Engineering,  14  (1): (121100).  [PMID:] [10.1016/j.jece.2026.121100]

16. Long Cheng, Hui Li, Chengyi Luo, Yibo Zhang, Kai Cheng, Siyang Wang, Zhiquan Hu.  (2026)  In situ reactivation of aerobic granular sludge after extended idle conditions: Effect of different N-acyl-homoserine lactones (AHLs).  JOURNAL OF ENVIRONMENTAL MANAGEMENT,      [PMID:41655310] [10.1016/j.jenvman.2026.128866]

17. Qian Zhang, Fu Wei, Shumin Qin, Bixiang Nie, Lin Deng, Zheng Chen, Siyu Hua.  (2026)  Optimizing HN-AD bacteria-Chlorella symbiotic system via QS molecules for biogas slurry treatment.  Journal of Environmental Chemical Engineering,  14  (3): (122219).  [PMID:] [10.1016/j.jece.2026.122219]