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N-Decanoyl-L-homoserine lactone (C10-HSL) 177315-87-6

N-Decanoyl-L-homoserine lactone (C10-HSL) 177315-87-6

CAS No.: 177315-87-6

N-decanoyl-L-homoserine lactone (C10-HSL) is an N-acyl-homoserine lactone (AHL). N-decanoyl-L-homoserine lactone inhibit
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N-decanoyl-L-homoserine lactone (C10-HSL) is an N-acyl-homoserine lactone (AHL). N-decanoyl-L-homoserine lactone inhibits taproot growth of Arabidopsis thaliana. N-decanoyl-L-homoserine lactone treatment can cause a transient and immediate increase in cytoplasmic free Ca2+ and reactive oxygen species (ROS) concentrations in Arabidopsis thaliana roots, increase the activity of mitogen-activated protein kinase 6 (MPK6), and induce monoxide oxidation Nitrogen (NO) production.

Physicochemical Properties


Molecular Formula C14H25NO3
Molecular Weight 255.35
Exact Mass 255.183
CAS # 177315-87-6
PubChem CID 10131281
Appearance White to off-white solid powder
Density 1.0±0.1 g/cm3
Boiling Point 466.1±34.0 °C at 760 mmHg
Melting Point 127-130 °C (lit.)
Flash Point 235.7±25.7 °C
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.476
LogP 2.09
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 3
Rotatable Bond Count 9
Heavy Atom Count 18
Complexity 266
Defined Atom Stereocenter Count 1
SMILES

O1C([C@]([H])(C([H])([H])C1([H])[H])N([H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)=O

InChi Key TZWZKDULKILUPV-LBPRGKRZSA-N
InChi Code

InChI=1S/C14H25NO3/c1-2-3-4-5-6-7-8-9-13(16)15-12-10-11-18-14(12)17/h12H,2-11H2,1H3,(H,15,16)/t12-/m0/s1
Chemical Name

N-[(3S)-2-oxooxolan-3-yl]decanamide
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vitro In Arabidopsis, N-decanoyl-L-homoserine lactone (0-75 µM) reduces primary root growth and encourages the production of lateral roots [1]. In wild-type seedlings, N-decanoyl-L-homoserine lactone (0–30µM) can raise the cytosolic Ca2+ concentration [1]. Through cross-kingdom interactions, the bacterial signal N-decanoyl-L-homoserine lactone promotes the germination of Galactomyces geotrichum spores [2].
References [1]. Cao XY, et al. Cellular messengers involved in the inhibition of the Arabidopsis primary root growth by bacterial quorum-sensing signal N-decanoyl-L-homoserine lactone. BMC Plant Biol. 2022 Oct 14;22(1):488.
[2]. Xin Lu, et al. Bacterial signal C10-HSL stimulates spore germination of Galactomyces geotrichum by transboundary interaction. Chinese Chemical Letters. 2022.
Additional Infomation N-decanoyl-L-Homoserine lactone is a N-acyl-amino acid.
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide has been reported in Azospirillum lipoferum with data available.

Solubility Data


Solubility (In Vitro) DMSO : 100 mg/mL (391.62 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.5 mg/mL (9.79 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (9.79 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9162 mL 19.5810 mL 39.1619 mL
5 mM 0.7832 mL 3.9162 mL 7.8324 mL
10 mM 0.3916 mL 1.9581 mL 3.9162 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.