N-Dodecanoyl-L-homoserine lactone
| Code | Size | Price |
|---|
| CDX-D0335-M005 | 5 mg | £72.00 |
Quantity:
| CDX-D0335-M050 | 50 mg | £377.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide; dDHL; C12-HSL
Appearance:
White powder.
CAS:
137173-46-7
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light and moisture.
InChi:
InChI=1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1
InChiKey:
WILLZMOKUUPJSL-AWEZNQCLSA-N
Long Description:
Chemical. CAS: 137173-46-7. Formula: C16H29NO3. MW: 283.4. Synthetic. N-Dodecanoyl-L-homoserine lactone (C12-HSL) is a small diffusible signalling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. In addition to regulating bacterial functions, C12-HSL activates NF-kappaB in RAW 264.7 macrophages, increasing the expression of TNF-alpha, interleukin-1beta (IL-1beta) and IL-8, while other lactones do not. In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone, which is produced at different times in biofilm development and has different cellular effects.
MDL:
MFCD11976890
Molecular Formula:
C16H29NO3
Molecular Weight:
283.4
Package Type:
Vial
Product Description:
N-Dodecanoyl-L-homoserine lactone (C12-HSL) is a small diffusible signalling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. In addition to regulating bacterial functions, C12-HSL activates NF-kappaB in RAW 264.7 macrophages, increasing the expression of TNF-alpha, interleukin-1beta (IL-1beta) and IL-8, while other lactones do not. In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone, which is produced at different times in biofilm development and has different cellular effects.
Purity:
>98% (NMR)
SMILES:
CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
Solubility Chemicals:
Soluble in DMSO and dimethylformamide (approx. 30mg/ml).
Source / Host:
Synthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at +4°C.
References
(1) G.D. Geske; JACS 127, 12762 (2005) | (2) J.T. Hodgkinson; Tetrahedron Lett. 52, 3291 (2011) | (3) A. Kuo, et al.; J. Bacteriol. 176, 7558 (1994) | (4) J.K. Lithgow, et al.; Mol. Microbiol. 37, 81 (2000) | (5) K.H. McClean, et al.; Microbiol. 143, 3703 (1997) | (6) K. Gomi, et al.; Infect. Immun. 74, 7029 (2006) | (7) S. Kristiansen, et al.; APMIS 116, 361 (2008) | (8) Y. Huang, et al.; ISME 1, (2008)
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