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MedKoo Cat#: 592217 | Name: Disparlure

Description:

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

Disparlure is a potent sex pheromone used primarily for the monitoring and management of Lymantria dispar, commonly known as the gypsy moth. This compound, a cis- and trans- 7,8-epoxy-2-methyloctadecane mixture, is highly specific in attracting male gypsy moths, making it a valuable tool for population surveillance and mating disruption strategies. By deploying Disparlure in traps or as part of integrated pest management (IPM) programs, it helps detect infestations, limit moth reproduction, and reduce the spread of this invasive species. Its effectiveness, environmental safety, and species-specificity make it a widely used pheromone in forestry and agricultural pest control.

Chemical Structure

Disparlure
Disparlure
CAS#29804-22-6

Theoretical Analysis

MedKoo Cat#: 592217

Name: Disparlure

CAS#: 29804-22-6

Chemical Formula: C19H38O

Exact Mass: 282.2923

Molecular Weight: 282.51

Elemental Analysis: C, 80.78; H, 13.56; O, 5.66

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
(±)-cis-Disparlure; (±)-Disparlure; Atralymon; cis-7,8-Epoxy-2-methyloctadecane; Disparlure; ENT 34886; Epoxan; SPLAT GM
IUPAC/Chemical Name
cis-7,8-Epoxy-2-methyloctadecane
InChi Key
HFOFYNMWYRXIBP-MOPGFXCFSA-N
InChi Code
InChI=1S/C19H38O/c1-4-5-6-7-8-9-10-11-15-18-19(20-18)16-13-12-14-17(2)3/h17-19H,4-16H2,1-3H3/t18-,19+/m1/s1
SMILES Code
CC(C)CCCC[C@H](O1)[C@H]1CCCCCCCCCC
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 282.51 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
1: Klosowski DW, Hethcox JC, Paull DH, Fang C, Donald JR, Shugrue CR, Pansick AD, Martin SF. Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications. J Org Chem. 2018 Jun 1;83(11):5954-5968. doi: 10.1021/acs.joc.8b00490. Epub 2018 May 22. PubMed PMID: 29717607; PubMed Central PMCID: PMC5984189. 2: Klosowski DW, Martin SF. Correction to "Synthesis of (+)-Disparlure via Enantioselective Iodolactonization". Org Lett. 2018 May 4;20(9):2796. doi: 10.1021/acs.orglett.8b00999. Epub 2018 Apr 11. PubMed PMID: 29637784. 3: Klosowski DW, Martin SF. Synthesis of (+)-Disparlure via Enantioselective Iodolactonization. Org Lett. 2018 Mar 2;20(5):1269-1271. doi: 10.1021/acs.orglett.7b03911. Epub 2018 Feb 12. Erratum in: Org Lett. 2018 May 4;20(9):2796. PubMed PMID: 29431447; PubMed Central PMCID: PMC5834403. 4: Cardé RT, Bau J, Elkinton JS. Comparison of Attraction and Trapping Capabilities of Bucket- and Delta-Style Traps With Different Pheromone Emission Rates for Gypsy Moths (Lepidoptera: Erebidae): Implications for Understanding Range of Attraction and Utility in Surveillance. Environ Entomol. 2018 Feb 8;47(1):107-113. doi: 10.1093/ee/nvx185. PubMed PMID: 29281084. 5: Lance DR, Leonard DS, Mastro VC, Walters ML. Mating Disruption as a Suppression Tactic in Programs Targeting Regulated Lepidopteran Pests in US. J Chem Ecol. 2016 Jul;42(7):590-605. doi: 10.1007/s10886-016-0732-9. Epub 2016 Aug 4. Review. PubMed PMID: 27492468. 6: Sanes JT, Plettner E. Gypsy moth pheromone-binding protein-ligand interactions: pH profiles and simulations as tools for detecting polar interactions. Arch Biochem Biophys. 2016 Sep 15;606:53-63. doi: 10.1016/j.abb.2016.07.008. Epub 2016 Jul 16. PubMed PMID: 27431057. 7: Wang P, Chen GF, Zhang JS, Xue Q, Zhang JH, Chen C, Zhang QH. Pheromone-trapping the nun moth, Lymantria monacha (Lepidoptera: Lymantriidae) in Inner Mongolia, China. Insect Sci. 2017 Aug;24(4):631-639. doi: 10.1111/1744-7917.12350. Epub 2016 Jun 21. PubMed PMID: 27122095. 8: Mori K. Stereochemical aspects of pheromonal communications: diversity is the key word. J Chem Ecol. 2014 Mar;40(3):214. doi: 10.1007/s10886-014-0396-2. PubMed PMID: 24619726. 9: Onufrieva KS, Hickman AD, Leonard DS, Tobin PC. Efficacies and Second-Year Effects of SPLAT GM™ and SPLAT GM™ Organic Formulations. Insects. 2014 Dec 23;6(1):1-12. doi: 10.3390/insects6010001. PubMed PMID: 26463062; PubMed Central PMCID: PMC4553524. 10: Sollai G, Murgia S, Secci F, Frongia A, Cerboneschi A, Masala C, Liscia A, Crnjar R, Solari P. A pheromone analogue affects the evaporation rate of (+)-disparlure in Lymantria dispar. Pest Manag Sci. 2014 Apr;70(4):674-81. doi: 10.1002/ps.3609. Epub 2013 Aug 9. PubMed PMID: 23868283. 11: Yu Y, Plettner E. Enantiomer and conformer recognition of (+) and (-)-disparlure and their analogs by the pheromone binding proteins of the gypsy moth, Lymantria dispar. Bioorg Med Chem. 2013 Apr 1;21(7):1811-22. doi: 10.1016/j.bmc.2013.01.043. Epub 2013 Jan 31. PubMed PMID: 23434366. 12: Onufrieva KS, Thorpe KW, Hickman AD, Leonard DS, Roberts EA, Tobin PC. Persistence of the Gypsy Moth Pheromone, Disparlure, in the Environment in Various Climates. Insects. 2013 Jan 14;4(1):104-16. doi: 10.3390/insects4010104. PubMed PMID: 26466798; PubMed Central PMCID: PMC4553432. 13: Yu Y, Ma F, Cao Y, Zhang J, Zhang Y, Duan S, Wei Y, Zhu S, Chen N. Structural and functional difference of pheromone binding proteins in discriminating chemicals in the gypsy moth, Lymantria dispar. Int J Biol Sci. 2012;8(7):979-91. doi: 10.7150/ijbs.4557. Epub 2012 Jul 30. PubMed PMID: 22904666; PubMed Central PMCID: PMC3421229. 14: Tobin PC, Zhang A, Onufrieva K, Leonard DS. Field evaluation of effect of temperature on release of disparlure from a pheromone-baited trapping system used to monitor gypsy moth (Lepidoptera: Lymantriidae). J Econ Entomol. 2011 Aug;104(4):1265-71. PubMed PMID: 21882691. 15: Gong Y, Plettner E. Effects of aromatic compounds on antennal responses and on the pheromone-binding proteins of the gypsy moth (Lymantria dispar). Chem Senses. 2011 Mar;36(3):291-300. doi: 10.1093/chemse/bjq130. Epub 2010 Dec 15. PubMed PMID: 21159920. 16: Chen H, Gong Y, Gries RM, Plettner E. Synthesis and biological activity of conformationally restricted gypsy moth pheromone mimics. Bioorg Med Chem. 2010 Apr 15;18(8):2920-9. doi: 10.1016/j.bmc.2010.02.061. Epub 2010 Mar 6. PubMed PMID: 20347316. 17: Plettner E, Gries R. Agonists and antagonists of antennal responses of gypsy moth (Lymantria dispar) to the pheromone (+)-disparlure and other odorants. J Agric Food Chem. 2010 Mar 24;58(6):3708-19. doi: 10.1021/jf904139e. PubMed PMID: 20192223. 18: Gong Y, Pace TC, Castillo C, Bohne C, O'Neill MA, Plettner E. Ligand-interaction kinetics of the pheromone- binding protein from the gypsy moth, L. dispar: insights into the mechanism of binding and release. Chem Biol. 2009 Feb 27;16(2):162-72. doi: 10.1016/j.chembiol.2009.01.005. PubMed PMID: 19246007. 19: Gries R, Schaefer PW, Hahn R, Khaskin G, Ramaseshiah G, Singh B, Hehar GK, Gries G. Sex pheromone components of Indian gypsy moth, Lymantria obfuscata. J Chem Ecol. 2007 Sep;33(9):1774-86. Epub 2007 Jul 20. PubMed PMID: 17641931. 20: Solari P, Crnjar R, Frongia A, Sollai G, Secci F, Spiga M, Masala C, Liscia A. Oxaspiropentane derivatives as effective sex pheromone analogues in the gypsy moth: electrophysiological and behavioral evidence. Chem Senses. 2007 Oct;32(8):755-63. Epub 2007 Jul 14. PubMed PMID: 17630413.

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