Nepetalactone

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584700

CAS#: 490-10-8

Description: Nepetalactone is found in the plant Nepeta parnassica and has high mosquito repellency properties.

Chemical Structure

img
Nepetalactone
CAS# 490-10-8
Instruction

Theoretical Analysis

MedKoo Cat#: 584700
Name: Nepetalactone
CAS#: 490-10-8
Chemical Formula: C10H14O2
Exact Mass: 166.10
Molecular Weight: 166.220
Elemental Analysis: C, 72.26; H, 8.49; O, 19.25

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Nepetalactone; MD(sub 1) 84; MDI 84; MDI-84; MDI84;

IUPAC/Chemical Name: Cyclopenta(c)pyran-1-(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-

InChi Key: ZDKZHVNKFOXMND-UHFFFAOYSA-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

SMILES Code: O=C1C2C(CCC2C)C(C)=CO1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 166.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Sparks JT, Bohbot JD, Ristic M, Mišic D, Skoric M, Mattoo A, Dickens JC. Chemosensory Responses to the Repellent Nepeta Essential Oil and Its Major Component Nepetalactone by Aedes aegypti (Diptera: Culicidae), a Vector of Zika Virus. J Med Entomol. 2017 Jul 1;54(4):957-963. doi: 10.1093/jme/tjx059. PubMed PMID: 28407077.

2: Dehghany Ashkezary M, Aboee-Mehrizi F, Moradi P. SiO(2)@antisense molecules covered by nepetalactone, extracted from Nepeta gloeocephala, inhibits ILK phosphorylation and downstream PKB/AKT signaling in HeLa cells. Cancer Gene Ther. 2017 Jan;24(1):28-32. doi: 10.1038/cgt.2016.75. Epub 2016 Dec 16. PubMed PMID: 27982018.

3: Sherden NH, Lichman B, Caputi L, Zhao D, Kamileen MO, Buell CR, O'Connor SE. Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry. Phytochemistry. 2018 Jan;145:48-56. doi: 10.1016/j.phytochem.2017.10.004. Epub 2017 Nov 5. PubMed PMID: 29091815; PubMed Central PMCID: PMC5739345.

4: Sim J, Yoon I, Yun H, An H, Suh YG. Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone. Org Biomol Chem. 2016 Jan 28;14(4):1244-51. doi: 10.1039/c5ob02147b. Epub 2015 Dec 8. PubMed PMID: 26647357.

5: Nestorović J, Misić D, Siler B, Soković M, Glamoclija J, Cirić A, Maksimović V, Grubisić D. Nepetalactone content in shoot cultures of three endemic Nepeta species and the evaluation of their antimicrobial activity. Fitoterapia. 2010 Sep;81(6):621-6. doi: 10.1016/j.fitote.2010.03.007. Epub 2010 Mar 20. PubMed PMID: 20307630.

6: Gkinis G, Michaelakis A, Koliopoulos G, Ioannou E, Tzakou O, Roussis V. Evaluation of the repellent effects of Nepeta parnassica extract, essential oil, and its major nepetalactone metabolite against mosquitoes. Parasitol Res. 2014 Mar;113(3):1127-34. doi: 10.1007/s00436-013-3750-3. Epub 2014 Jan 22. PubMed PMID: 24449446.

7: Bol S, Caspers J, Buckingham L, Anderson-Shelton GD, Ridgway C, Buffington CA, Schulz S, Bunnik EM. Responsiveness of cats (Felidae) to silver vine (Actinidia polygama), Tatarian honeysuckle (Lonicera tatarica), valerian (Valeriana officinalis) and catnip (Nepeta cataria). BMC Vet Res. 2017 Mar 16;13(1):70. doi: 10.1186/s12917-017-0987-6. PubMed PMID: 28302120; PubMed Central PMCID: PMC5356310.

8: Fernández-Grandon GM, Woodcock CM, Poppy GM. Do asexual morphs of the peach-potato aphid, Myzus persicae, utilise the aphid sex pheromone? Behavioural and electrophysiological responses of M. persicae virginoparae to (4aS,7S,7aR)-nepetalactone and its effect on aphid performance. Bull Entomol Res. 2013 Aug;103(4):466-72. doi: 10.1017/S0007485313000126. Epub 2013 Mar 13. PubMed PMID: 23480367.

9: Shafaghat A, Oji K. Nepetalactone content and antibacterial activity of the essential oils from different parts of Nepeta persica. Nat Prod Commun. 2010 Apr;5(4):625-8. PubMed PMID: 20433086.

10: Birkett MA, Hassanali A, Hoglund S, Pettersson J, Pickett JA. Repellent activity of catmint, Nepeta cataria, and iridoid nepetalactone isomers against Afro-tropical mosquitoes, ixodid ticks and red poultry mites. Phytochemistry. 2011 Jan;72(1):109-14. doi: 10.1016/j.phytochem.2010.09.016. Epub 2010 Nov 4. PubMed PMID: 21056438.

11: Aydin S, Beis R, Oztürk Y, Baser KH. Nepetalactone: a new opioid analgesic from Nepeta caesarea Boiss. J Pharm Pharmacol. 1998 Jul;50(7):813-7. Erratum in: J Pharm Pharmacol 1998 Oct;50(10):1204. Baser C [corrected to Baser KH]. PubMed PMID: 9720633.

12: Waller GR, Price GH, Mitchell ED. Feline attractant, cis,trans-nepetalactone: metabolism in the domestic cat. Science. 1969 Jun 13;164(3885):1281-2. PubMed PMID: 5770619.

13: Liblikas I, Santangelo EM, Sandell J, Baeckström P, Svensson M, Jacobsson U, Unelius CR. Simplified isolation procedure and interconversion of the diastereomers of nepetalactone and nepetalactol. J Nat Prod. 2005 Jun;68(6):886-90. PubMed PMID: 15974613.

14: Sonboli A, Saadat MH, Arman M, Kanani MR. Antibacterial activity and composition of the essential oil of Nepeta hormozganica Jamzad from Iran. Nat Prod Res. 2017 Dec;31(23):2806-2809. doi: 10.1080/14786419.2017.1295237. Epub 2017 Mar 1. PubMed PMID: 28278630.

15: Pettersson M, Unelius CR, Valterová I, Borg-Karlson AK. Semiochemicals related to the aphid Cinara pilicornis and its host, Picea abies: a method to assign nepetalactone diastereomers. J Chromatogr A. 2008 Feb 8;1180(1-2):165-70. doi: 10.1016/j.chroma.2007.12.020. Epub 2007 Dec 15. PubMed PMID: 18166192.

16: Wang M, Cheng KW, Wu Q, Simon JE. Quantification of nepetalactones in catnip (Nepeta cataria L.) by HPLC coupled with ultraviolet and mass spectrometric detection. Phytochem Anal. 2007 Mar-Apr;18(2):157-60. PubMed PMID: 17439017.

17: Fernández-Grandon GM, Poppy GM. Response of Aphidius colemani to aphid sex pheromone varies depending on plant synergy and prior experience. Bull Entomol Res. 2015 Aug;105(4):507-14. doi: 10.1017/S0007485315000371. Epub 2015 May 20. PubMed PMID: 25991073.

18: Kekeç G, Mutlu S, Alpsoy L, Sakçali MS, Atici Ö. Genotoxic effects of catmint (Nepeta meyeri Benth.) essential oils on some weed and crop plants. Toxicol Ind Health. 2013 Jul;29(6):504-13. doi: 10.1177/0748233712440135. Epub 2012 Mar 20. PubMed PMID: 22434692.

19: Ganzera M, Crockett S, Tellez MR, Khan IA. Determination of nepetalactone in Nepeta cataria by reversed phase high performance liquid chromatography. Pharmazie. 2001 Nov;56(11):896-7. PubMed PMID: 11817179.

20: Aldrich JR, Chauhan K, Zhang QH. Pharmacophagy in green lacewings (Neuroptera: Chrysopidae: Chrysopa spp.)? PeerJ. 2016 Jan 18;4:e1564. doi: 10.7717/peerj.1564. eCollection 2016. PubMed PMID: 26819841; PubMed Central PMCID: PMC4727961.