| Identification | Back Directory | [Name]
DDHL | [CAS]
137173-46-7 | [Synonyms]
DDHL
C12-HSL
C12-HOMOSERINE LACTONE
N-Lauroyl-L-homoserine lactone
Dodecanoyl-L-hoMoserine lactone
N-DODECANOYL-L-HOMOSERINE LACTONE
N-[(3S)-2-oxooxolan-3-yl]dodecanamide
N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide
C12-HSL, dDHL, N-Dodecanoyl-L-hoMoserine lactone | [Molecular Formula]
C16H29NO3 | [MDL Number]
MFCD11976890 | [MOL File]
137173-46-7.mol | [Molecular Weight]
283.41 |
| Chemical Properties | Back Directory | [Melting point ]
128 °C(Solv: ethyl acetate (141-78-6)) | [Boiling point ]
485.8±34.0 °C(Predicted) | [density ]
1.00±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Chloroform: 10 mg/ml; DMF: 1 mg/ml; DMSO: 1 mg/ml | [form ]
A crystalline solid | [pka]
14.71±0.20(Predicted) | [color ]
White to off-white | [optical activity]
[α]/D -25±5°, c = 0.2 in methanol | [BRN ]
9281984 |
| Hazard Information | Back Directory | [Uses]
Dodecanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Sinorhizobium meliloti. N-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. | [Uses]
Dodecanoyl-L-homoserine lactone was confirmed to be an active quorum sensing modulator first recognised in Sinorhizobium meliloti. N-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: An N-acyl-L-homoserine lactone having dodecanoyl as the acyl substituent. | [Biochem/physiol Actions]
N-Dodecanoyl-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. | [storage]
Store at -20°C |
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