N-3-Oxo-tetradecanoyl-L-homoserine lactone (oxo-C14-HSL) is a rhizosphere bacterial inducer that improves basic defenses against nematodes.

Physicochemical Properties

Molecular Formula	C18H31NO4
Molecular Weight	325.44
Exact Mass	325.225
CAS #	177158-19-9
PubChem CID	9883786
Appearance	White to off-white solid powder
Density	1.0±0.1 g/cm3
Boiling Point	537.3±50.0 °C at 760 mmHg
Flash Point	278.7±30.1 °C
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.484
LogP	3.08
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	13
Heavy Atom Count	23
Complexity	381
Defined Atom Stereocenter Count	1
SMILES	O1C([C@]([H])(C([H])([H])C1([H])[H])N([H])C(C([H])([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])C([H])([H])C([H])([H])[H])=O)=O)=O
InChi Key	YQFJJDSGBAAUPW-INIZCTEOSA-N
InChi Code	InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1
Chemical Name	3-oxo-N-[(3S)-2-oxooxolan-3-yl]tetradecanamide
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

Targets	rhizobacterial[1]
ln Vitro	Rhizobacterial inducer: N-3-Oxo-tetradecanoyl-L-homoserine lactone. A better first line of defense against nematodes is provided by N-3-Oxo-tetradecanoyl-L-homoserine[1].
References	[1]. Priming Soybean cv. Primus Leads to Successful Systemic Defense Against the Root-Lesion Nematode, Pratylenchus penetrans. Front Plant Sci. 2021;12:651943. Published 2021 May 12.
Additional Infomation	3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide is a monocarboxylic acid amide that is tetradecanamide substituted by an oxo group at position 3 and a (3S)-2-oxotetrahydrofuran-3-yl group at the N atom. It is a gamma-lactone, a member of furans and a monocarboxylic acid amide.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (307.28 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 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	3.0728 mL	15.3638 mL	30.7276 mL
	5 mM	0.6146 mL	3.0728 mL	6.1455 mL
	10 mM	0.3073 mL	1.5364 mL	3.0728 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.