4aα,7α,7aα-Nepetalactone has anti-bacterial effect and inhibits Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Enterococcus faecalis.

Physicochemical Properties

Molecular Weight	166.22
Exact Mass	166.099
CAS #	21651-62-7
PubChem CID	161367
Appearance	Colorless to light yellow liquid
Density	1.0±0.1 g/cm3
Boiling Point	270.6±19.0 °C at 760 mmHg
Flash Point	107.7±18.9 °C
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.485
LogP	2.83
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Heavy Atom Count	12
Complexity	242
Defined Atom Stereocenter Count	3
SMILES	O1C=C(C)[C@@]2([H])CC[C@H](C)[C@@]2([H])C1=O
InChi Key	ZDKZHVNKFOXMND-NBEYISGCSA-N
InChi Code	InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8+,9+/m0/s1
Chemical Name	(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
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: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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

References

[1]. Nepetalactone content and antibacterial activity of the essential oils from different parts of Nepeta persica. Nat Prod Commun. 2010 Apr;5(4):625-8.

Additional Infomation

Cis-trans-nepetalactone is a cyclopentapyran that is (4aS,7aR)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aR-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It is an aphid sex pheromone and cat attractant, and exhibits antibacterial, antifungal, and analgesic properties. It has a role as a pheromone, a plant metabolite, an insect attractant, an analgesic, an insect repellent, an antibacterial agent and an antifungal agent. It is an iridoid monoterpenoid and a cyclopentapyran. Nepetalactone cis-trans-form has been reported in Nepeta tuberosa, Nepeta cataria, and Nepeta racemosa with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (601.61 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (15.04 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (15.04 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 3: ≥ 2.5 mg/mL (15.04 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	6.0161 mL	30.0806 mL	60.1612 mL
	5 mM	1.2032 mL	6.0161 mL	12.0322 mL
	10 mM	0.6016 mL	3.0081 mL	6.0161 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.