ChemicalBook > CAS DataBase List > 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide

3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide

Product Name: 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
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
Formula Weight: 297.39
MOL File: 168982-69-2.mol

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3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Property

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

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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.

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

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: O9139
Product name: N-(3-Oxododecanoyl)-L-homoserine lactone
Purity: quorum sensing signaling molecule
Packaging: 10MG
Price: $92.4
Updated: 2025/07/31

Sigma-Aldrich

Product number: O9139
Product name: N-(3-Oxododecanoyl)-L-homoserine lactone
Purity: quorum sensing signaling molecule
Packaging: 100MG
Price: $420
Updated: 2025/07/31

Cayman Chemical

Product number: 10007895
Product name: N-3-oxo-dodecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 1mg
Price: $33
Updated: 2024/03/01

Cayman Chemical

Product number: 10007895
Product name: N-3-oxo-dodecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 5mg
Price: $107
Updated: 2024/03/01

Cayman Chemical

Product number: 10007895
Product name: N-3-oxo-dodecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 10mg
Price: $196
Updated: 2024/03/01

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3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Chemical Properties,Usage,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

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168982-69-2, 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamideRelated Search:

3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide

N-(3-oxododecanoyl)-L-homoserine lactone L-enantiomer

N-(3-OXODODECANOYL)-L-HOMOSERINE

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Dodecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-

3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide

N-(3-Oxododecanoyl)-L-homoserine lactone, involved in quorum sensing

<i>N</i>-(3-Oxododecanoyl)-<sc>L</sc>-homoserine lactone

168982-69-2