N-Octanoyl-L-homoserine lactone (C8-HSL) - Moligand™, ≥98% , Agonist of TAS2R14, CAS No.147852-84-4, Agonist of TAS2R14

CAS: 147852-84-4 Cat. No.: O275948 Molecular Weight: 227.3

GRADE & PURITY Moligand™, ≥98%

Synonyms

C8-HSL | DTXSID301305072 | MFCD11113139 | Q27097162 | (S)-N-(2-Oxotetrahydrofuran-3-yl)octanamide | N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide | UNII-4A2B091F0G | N-OCTANOYL-L-HOMOSERINE LACTONE | Octanoyl-L-homoserine lactone | AS-67960 | C21199

Storage

Protected from light,Store at -20°C,Argon charged,Desiccated

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

C8-HSL | DTXSID301305072 | MFCD11113139 | Q27097162 | (S)-N-(2-Oxotetrahydrofuran-3-yl)octanamide | N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide | UNII-4A2B091F0G | N-OCTANOYL-L-HOMOSERINE LACTONE | Octanoyl-L-homoserine lactone | AS-67960 | C21199

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Autoinducer involved in quorum sensing. Member of N-acyl-homoserine lactone (AHL) family that regulate gene expression in gram-negative bacteria and are involved in the processes of bacterial quorum sensing.

Storage

Protected from light, 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.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of TAS2R14

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

• Pubchem Sid: 504764329
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764329
• Canonical Smiles: O=C1OCC[C@@H]1NC(CCCCCCC)=O
• IUPAC Name: N-[(3S)-2-oxooxolan-3-yl]octanamide
• InChIKey: JKEJEOJPJVRHMQ-JTQLQIEISA-N
• INCHI: 1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1
• Isomeric SMILES: CCCCCCCC(=O)N[C@H]1CCOC1=O
• Alternate CAS: 147852-84-4
• MeSH Entry Terms: AI-2 autoinducer;autoinducer 2;C8HSL compound;N-octanoyl-HSL;N-octanoyl-L-homoserine lactone;N-octanoylhomoserine lactone;VAI-2
• Molecular Weight: 227.3
• Reaxy-Rn: 8148282
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8148282&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 Tetrahydrofurans Secondary carboxylic acid amides Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds 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 - Tetrahydrofuran - Carboxamide group - Carboxylic acid ester - Lactone - Secondary carboxylic acid amide - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic oxide - 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: fatty amide - butan-4-olide

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

Associated Targets(Human)

TAS2R14 Tchem Taste receptor type 2 member 14 (0 Activities)

Discover Target: TAS2R14

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Associated Targets(non-human)

luxR Transcriptional activator protein luxR (400 Activities)

Discover Target: luxR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

traR Transcriptional activator protein traR (147 Activities)

Discover Target: traR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lasR Transcriptional activator protein lasR (432 Activities)

Discover Target: lasR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO
• Sensitivity: Light sensitive；Heat sensitive;Air sensitive
• Melt Point(°C): 136 °C
• Molecular Weight: 227.300 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 227.152 Da
• Monoisotopic Mass: 227.152 Da
• Topological Polar Surface Area: 55.400 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 240.000
• 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. 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]

2. Lianjie Wang, Siyi Jing, Jie Gao, Pengcheng Xia, Tongtong Dou, Weiwei Wang, Ming Zhang, Weichuan Qiao.  (2025)  Enhancement of aerobic sludge granulation by quorum sensing signaling molecules mediated by biomimetic bacterial extracellular vesicles.  JOURNAL OF ENVIRONMENTAL MANAGEMENT,      [PMID:39884203] [10.1016/j.jenvman.2025.124342]

3. Bin Cui, Sixin Zhang, Chunrui Li, Wenxin Xu, Dandan Zhou.  (2025)  Collapse of quorum sensing networks underlies low-temperature failure of ammonia oxidation.  BIORESOURCE TECHNOLOGY,      [PMID:41015304] [10.1016/j.biortech.2025.133392]

4. Zhiqi Lu, Mengzhe Zhao, Xianglong He, Hongjing Li.  (2025)  Biochar-Enhanced Nitrogen Removal in SBBR Under PFOA Stress: The Role of Quorum Sensing.  Sustainability,  17  (8): (3359).  [PMID:] [10.3390/su17083359]

5. Shumin Qin, Lin Deng, Yan Lin, Lang Jiang, Xilong Liu, Qian Zhang.  (2025)  Quorum sensing signaling molecules enhance the treatment performance of the HN-AD bacteria-Chlorella symbiotic system in MABR.  JOURNAL OF ENVIRONMENTAL MANAGEMENT,      [PMID:40743974] [10.1016/j.jenvman.2025.126783]

6. Shumin Qin, Bixiang Nie, Fu Wei, Yan Lin, Lang Jiang, Qian Zhang.  (2025)  Quorum sensing molecules promote the nutrients removal in a HN-AD bacteria-Chlorella symbiotic system.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.168245]

7. 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]

8. 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]