Chemistry:Ethyl butylacetylaminopropionate
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| Names | |
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| IUPAC name
Ethyl N-acetyl-N-butyl-β-alaninate
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| Preferred IUPAC name
Ethyl 3-(N-butylacetamido)propanoate | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| Properties | |
| C11H21NO3 | |
| Molar mass | 215.293 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Almost odorless |
| Density | 0.998 g/cm3 (at 20 °C) |
| Melting point | < -90 °C |
| Boiling point | 141 °C (decomposes) |
| 70 g/L (at 20 °C) | |
| Solubility in Acetone, ethyl acetate, dichloromethane, n-heptane, methanol, p-xylene | >250 g/L (at RT) |
| log P | 1.7 (at 23 °C) |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | Warning |
| H319 | |
| P280, P305+351+338, P337+313 | |
| Flash point | 159 °C (318 °F; 432 K) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Ethyl butylacetylaminopropionate is an insect repellent whose trade name is IR3535 and was developed and commercialized by Merck KGaA (Germany). It is a colorless and odorless oil with a good skin feel in final products, and it is biodegradable.[1][2][3]
Unlike icaridin, IR3535 can dissolve some plastics and synthetic fabrics, except polyethylene and polypropylene.[4][5][6]
Effectiveness
IR3535 is effective in repelling several different insects such as mosquitoes species and also midges, ticks and head lice. It is as effective as DEET against Aedes and Culex mosquitoes, but may be less effective than DEET against Anopheles mosquitoes, vectors of malaria.[7][8]
A 2013 review concluded that IR3535 is as effective as 20% DEET against Anopheles, citing that some studies reported possibly shorter protection of just 3.8 hours.[9][6] In areas with malaria, the NHS recommends 50% DEET or at least 30% DEET or 20% icaridin instead of IR3535.[10][11][12] IR3535, among other repellents, is included in the World Health Organization (WHO) recommendation for areas with malaria. The WHO also notes that it may be necessary to reapply repellents every 3-4 hours in hot and humid climates.[13][14]
IR3535 also helps prevent bites from ticks that may transmit Lyme disease.[6]
Adverse effects
IR3535 can irritate the eyes on contact.[5]
Interactions
Few if any studies have evaluated possible interactions when using IR3535 with sunscreens.[15]
Mechanism of action
The mechanism of action is still under investigation, but it probably related to the intolerance of mosquitos and other invertebrate animals to its odor.
IR3535 is applied topically in human skin and prevent bites from mosquitos and ticks that might cause serious diseases, such as dengue, malaria, zika, West Nile virus, Lyme disease, among others.[16]
Chemistry
IR3535 is a derivative of non-proteinogenic amino acid beta-alanine.[2]
Approval
IR3535 is approved by several authorities around the world, including ECHA (Europe)[17] and the EPA (US)[18] where it is considered a biopesticide.
See also
- DEET
- Icaridin
- p-Menthane-3,8-diol (PMD)
- Permethrin, a pyrethroid insecticide that can be applied to clothing to help prevent bites
References
- ↑ Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
- ↑ 2.0 2.1 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (113509) Technical Document
- ↑ 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (IR3535) (113509) Fact Sheet
- ↑ "Insect Repellent - FAQ". Merck. https://www.merckgroup.com/en/expertise/cosmetics/care-solutions/insect-repellent/faq.html. "Like a number of other repellents, IR3535® is not compatible with certain synthetic materials."
- ↑ 5.0 5.1 "EWG’s 2018 Guide to Bug Repellents". Environmental Working Group. 17 July 2018. https://www.ewg.org/consumer-guides/ewgs-2018-guide-bug-repellents.
- ↑ 6.0 6.1 6.2 "Insect Repellents". National Capital Poison Center. https://www.poison.org/articles/insect-repellent. "IR3535 20% offers protection against Aedes and Culex mosquitoes for 7-10 hours but only 3.8 hours of protection against Anopheles in some studies. Therefore, IR3535 is not recommended for use in malaria-endemic areas. It is a serious eye irritant but otherwise has a good safety profile. It can melt some plastics and damage some fabrics."
- ↑ "Expert Review of the Evidence Base for Arthropod Bite Avoidance". Journal of Travel Medicine 17 (3): 182–192. 1 May 2010. doi:10.1111/j.1708-8305.2010.00402.x. ISSN 1195-1982. https://academic.oup.com/jtm/article-lookup/doi/10.1111/j.1708-8305.2010.00402.x.
- ↑ Diaz, James H. (March 2016). "Chemical and Plant-Based Insect Repellents: Efficacy, Safety, and Toxicity". Wilderness & Environmental Medicine 27 (1): 153–163. doi:10.1016/j.wem.2015.11.007. https://linkinghub.elsevier.com/retrieve/pii/S1080603215004342.
- ↑ "The efficacy of repellents against Aedes, Anopheles, Culex and Ixodes spp. – A literature review". Travel Medicine and Infectious Disease 11 (6): 374–411. November 2013. doi:10.1016/j.tmaid.2013.10.005. https://linkinghub.elsevier.com/retrieve/pii/S1477893913001737.
- ↑ "Malaria". NHS. https://www.nhs.uk/conditions/malaria/. "use insect repellent on your skin – make sure it's 50% DEET-based"
- ↑ "Mosquito bite avoidance: advice for travellers". Gov.uk. https://www.gov.uk/government/publications/mosquito-bite-avoidance-for-travellers/mosquito-bite-avoidance-advice-for-travellers--2. "A product with 50% DEET is recommended as a first choice. If DEET is not tolerated, use of a repellent containing the highest strength formulation available of either icaridin (20%), eucalyptus citriodora oil, hydrated, cyclised or 3-ethlyaminopropionate is recommended."
- ↑ Team, HPS Travel Health. "Mosquito Bite Avoidance - Fit for Travel". https://www.fitfortravel.nhs.uk/advice/malaria/mosquito-bite-avoidance.aspx. "IR3535: less effective than DEET or Icaridin at preventing bites from the type of mosquitos that carry malaria; should not be used in countries where malaria is present"
- ↑ "Malaria". World Health Organization. 2023-03-29. https://www.who.int/news-room/fact-sheets/detail/malaria.
- ↑ "Malaria". International Travel and Health. World Health Organization. 2020. ISBN 978-92-4-158047-2. https://cdn.who.int/media/docs/default-source/travel-and-health/9789241580472-eng-chapter-7.pdf. Retrieved 2023-09-30.
- ↑ "Insect Repellents". National Pesticide Information Center. February 2018. http://npic.orst.edu/factsheets/repellents.html. "Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens."
- ↑ Lo, Wai Ling; Mok, Ka Leung; Yu Pui Ming, Stephanie Dorothy (2018-09-01). "Which insect repellents should we choose? Implications from results of local market survey and review of current guidelines" (in en). Hong Kong Journal of Emergency Medicine 25 (5): 272–280. doi:10.1177/1024907918773630. ISSN 1024-9079. https://doi.org/10.1177/1024907918773630.
- ↑ "Regulation (EU) 528/2012 evaluation of active substances / Assessment Report / Ethyl butylacetylaminopropionate / Product-type 19 (insect repellent)". March 13, 2014. https://echa.europa.eu/documents/10162/aaf5b78c-82ca-40a3-25a4-1cc4339c9407.
- ↑ Environmental Protection Agency (Feb 3, 2020). "3-[N-butyl-N-acetyl-aminopropionic acid, ethyl ester (IR3535) Interim Registration Review Decision Case Number 6046"]. https://www.regulations.gov/document/EPA-HQ-OPP-2014-0106-0009.
External links
- Barnard, Donald R.; Bernier, Ulrich R.; Posey, Kenneth H.; Xue, Rui-De (2002). "Repellency of IR3535, KBR3023, para-menthane-3,8-diol, and DEET to Black Salt Marsh Mosquitoes (Diptera: Culicidae) in the Everglades National Park". Journal of Medical Entomology 39 (6): 895–899. doi:10.1603/0022-2585-39.6.895. PMID 12495189. http://ddr.nal.usda.gov/bitstream/10113/6633/1/IND23332072.pdf.
- Tick Bite Prevention & the Use of Insect Repellents
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