3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
![3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Structure](CAS/GIF/168982-69-2.gif)
- CAS No.
- 168982-69-2
- Chemical Name:
- 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
- Synonyms
- N-(3-OXODODECANOYL)-L-HOMOSERINE;3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide;(S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)dodecanamide;N-(3-oxododecanoyl)-L-homoserine lactone L-enantiomer;3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide;Dodecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-;N-(3-Oxododecanoyl)-
L -homoserine lactone;N-(3-Oxododecanoyl)-L-homoserine lactone, involved in quorum sensing
- CBNumber:
- CB82489993
- Molecular Formula:
- C16H27NO4
- Molecular Weight:
- 297.39
- MDL Number:
- MFCD08275140
- MOL File:
- 168982-69-2.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Product description | Number | Pack Size | Price |
| N-(3-Oxododecanoyl)-L-homoserine lactone quorum sensing signaling molecule | O9139 | 10MG | $97.7 |
| N-(3-Oxododecanoyl)-L-homoserine lactone quorum sensing signaling molecule | O9139 | 100MG | $447 |
| N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 10007895 | 1mg | $37 |
| N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 10007895 | 5mg | $118 |
| N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 10007895 | 10mg | $216 |
| Melting point | 80-81 °C |
|---|---|
| Boiling point | 519.4±50.0 °C(Predicted) |
| Density | 1.06 |
| storage temp. | -20°C |
| solubility | ≤20mg/ml in DMSO;20mg/ml in dimethyl formamide |
| form | crystalline solid |
| pka | 11.22±0.46(Predicted) |
| color | White to light yellow |
| Major Application | cell analysis |
| InChI | 1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1 |
| InChIKey | PHSRRHGYXQCRPU-AWEZNQCLSA-N |
| SMILES | CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O |
| UNSPSC Code | 12352209 |
| NACRES | NA.26 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P305+P351+P338 | |||||||||
| PPE | dust mask type N95 (US), Eyeshields, Gloves | |||||||||
| WGK Germany | WGK 3 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Acute Tox. 4 Oral | |||||||||
| NFPA 704 |
|
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide price More Price(45)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | O9139 | N-(3-Oxododecanoyl)-L-homoserine lactone quorum sensing signaling molecule | 168982-69-2 | 10MG | $97.7 | 2026-04-30 | Buy |
| Sigma-Aldrich | O9139 | N-(3-Oxododecanoyl)-L-homoserine lactone quorum sensing signaling molecule | 168982-69-2 | 100MG | $447 | 2026-04-30 | Buy |
| Cayman Chemical | 10007895 | N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 168982-69-2 | 1mg | $37 | 2026-04-30 | Buy |
| Cayman Chemical | 10007895 | N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 168982-69-2 | 5mg | $118 | 2026-04-30 | Buy |
| Cayman Chemical | 10007895 | N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 168982-69-2 | 10mg | $216 | 2026-04-30 | Buy |
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Chemical Properties,Uses,Production
Description
N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) is a bacterial quorum-sensing signaling molecule produced by P. aeruginosa and strains of the B. cepacia complex. It induces the production of IL-8 in 16HBE human bronchial epithelial cells when used at a concentration of 100 μM. Supernatants from 3-oxo-C12-HSL-stimulated 16HBE cells induce chemotaxis of isolated human neutrophils. 3-oxo-C12-HSL has been found in respiratory secretions from patients with cystic fibrosis infected with P. aeruginosa.
Uses
N-(3-Oxododecanoyl)-L-homoserine Lactone is a bacterial quorum sensing signal molecule. Inhibits lymphocyte proliferation and TNF-α and IL-12 production by LPS-stimulated macrophages. Inhibits or promotes antibody production at high and low concentrations, respectively, in keyhole limpet hemocyanin (KLH)-stimulated spleen cells.
Definition
ChEBI: N-(3-oxododecanoyl)-L-homoserine lactone is an N-acyl-L-homoserine lactone having 3-oxododecanoyl as the acyl substituent. It has a role as a bacterial metabolite. It is a N-(3-oxododecanoyl)homoserine lactone and a N-acyl-L-homoserine lactone. It is an enantiomer of a N-(3-oxododecanoyl)-D-homoserine lactone.
Biochem/physiol Actions
N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL) is among a group of homoserine lactones that includes: N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
storage
Store at -20°C
References
[1]. henke jm, bassler bl. bacterial social engagements. trends cell biol. 2004 nov;14(11):648-56.
[2]. chambers ce, visser mb, schwab u, et al. identification of n-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. fems microbiol lett. 2005 mar 15;244(2):297-304.
[3]. smith rs, fedyk er, springer ta, et al. il-8 production in human lung fibroblasts and epithelial cells activated by the pseudomonas autoinducer n-3-oxododecanoyl homoserine lactone is transcriptionally regulated by nf-kappa b and activator protein-2. j immunol. 2001 jul 1;167(1):366-74.
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Preparation Products And Raw materials
Raw materials
Preparation Products
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| BOC Sciences | 16314854226; +8616314854226 | inquiry@bocsci.com | United States | 19852 | 58 |
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| SHANGHAI KEAN TECHNOLOGY CO., LTD. | +8613817748580 | cooperation@kean-chem.com | China | 40048 | 58 |
| ShangHai YuanYe Biotechnology Co., Ltd. | 13636370518 | shyysw007@163.com | China | 4998 | 60 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4773 | 55 |
| Shanghai Leto Pharmatech Co.,Ltd. | 86-021-5821 5861; 18016401466 | sales@letopharm.com | China | 235 | 58 |
