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Ethyl butylacetylaminopropionate

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Ethyl butylacetylaminopropionate
IR3535
Names
IUPAC name
Ethyl N-acetyl-N-butyl-β-alaninate
Preferred IUPAC name
Ethyl 3-(N-butylacetamido)propanoate
Other names
  • EBAAP
  • β-alanine, N-acetyl-N-butyl-, ethyl ester
  • IR3535
  • Insect Repellent 3535
  • BAAPE
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.052.560 Edit this at Wikidata
UNII
  • InChI=1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3 checkY
    Key: VZRKEAFHFMSHCD-UHFFFAOYSA-N checkY
  • CCCCN(CCC(=O)OCC)C(=O)C
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 labelling:
GHS07: Exclamation mark
Warning
H319
P280, P305+P351+P338, P337+P313
Flash point 159 °C (318 °F; 432 K)
Lethal dose or concentration (LD, LC):
  • >5000 mg/kg (rat, oral)
  • 10000 mg/kg (rate, dermal)
  • >5.1 mg/L (rat, inhalation)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

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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

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IR3535 can irritate the eyes on contact.[5]

Interactions

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Few if any studies have evaluated possible interactions when using IR3535 with sunscreens.[15]

Mechanism of action

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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

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Comparison of ethyl butylacetylaminopropionate and beta-alanine

IR3535 is a derivative of non-proteinogenic amino acid beta-alanine.[2]

Approval

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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

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References

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  1. ^ Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
  2. ^ a b 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (113509) Technical Document
  3. ^ 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (IR3535) (113509) Fact Sheet
  4. ^ "Insect Repellent - FAQ". Merck. Archived from the original on 22 September 2023. Retrieved 22 September 2023. Like a number of other repellents, IR3535® is not compatible with certain synthetic materials.
  5. ^ a b "EWG's 2018 Guide to Bug Repellents". Environmental Working Group. 17 July 2018. Archived from the original on 10 April 2021. Retrieved 9 August 2023.
  6. ^ a b c "Insect Repellents". National Capital Poison Center. Archived from the original on 1 June 2023. Retrieved 22 September 2023. 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.
  7. ^ Goodyer LI, Croft AM, Frances SP, Hill N, Moore SJ, Onyango SP, et al. (1 May 2010). "Expert Review of the Evidence Base for Arthropod Bite Avoidance". Journal of Travel Medicine. 17 (3): 182–192. doi:10.1111/j.1708-8305.2010.00402.x. ISSN 1195-1982.
  8. ^ 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.
  9. ^ Lupi E, Hatz C, Schlagenhauf P (November 2013). "The efficacy of repellents against Aedes, Anopheles, Culex and Ixodes spp. – A literature review". Travel Medicine and Infectious Disease. 11 (6): 374–411. doi:10.1016/j.tmaid.2013.10.005.
  10. ^ "Malaria". NHS. Archived from the original on 30 July 2023. Retrieved 22 September 2023. use insect repellent on your skin – make sure it's 50% DEET-based
  11. ^ "Mosquito bite avoidance: advice for travellers". Gov.uk. Archived from the original on 24 January 2023. Retrieved 22 September 2023. 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.
  12. ^ Team, HPS Travel Health. "Mosquito Bite Avoidance - Fit for Travel". Fit for Travel. Archived from the original on 7 August 2023. Retrieved 2023-08-07. 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
  13. ^ "Malaria". World Health Organization. 2023-03-29. Retrieved 2023-09-29.
  14. ^ "Malaria" (PDF). International Travel and Health. World Health Organization. 2020. ISBN 978-92-4-158047-2. Retrieved 2023-09-30.
  15. ^ "Insect Repellents". National Pesticide Information Center. February 2018. Archived from the original on 13 September 2023. Retrieved 26 September 2023. Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens.
  16. ^ 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". Hong Kong Journal of Emergency Medicine. 25 (5): 272–280. doi:10.1177/1024907918773630. ISSN 1024-9079.
  17. ^ Belgium (competent authority) (March 13, 2014). "Regulation (EU) 528/2012 evaluation of active substances / Assessment Report / Ethyl butylacetylaminopropionate / Product-type 19 (insect repellent)".
  18. ^ Environmental Protection Agency (Feb 3, 2020). "3-[N-butyl-N-acetyl]-aminopropionic acid, ethyl ester (IR3535) Interim Registration Review Decision Case Number 6046". www.regulations.gov.
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