Ethyl butylacetylaminopropionate

IR3535 (Ethyl butylacetylaminopropionate) is the trade name of an insect repellent developed and commercialized by Merck KGaA (Germany).

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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.052.560
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 ?)
Infobox references

The molecule is over 40 years in the market and it is considered the insect repellent of the future due to its excellent toxicological and environmental profile combined with great effectiveness against different insects.

Classification and approval

The World Health Organization (WHO) classifies IR3535® as Class U (unlikely to present acute hazard in normal use), while DEET and Picaridin are considered Class III (slightly hazardous).

IR3535® is approved by several authorities around the world, including ECHA (Europe) and the EPA (US) where it is considered a biopesticide.

Mode of action and effectiveness

IR3535® mechanism of action is still under investigation, but it probably related to the intolerance of mosquitos and other invertebrated animals to its odour.

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.[1]

IR3535® provides very strong efficacy in repelling several different insects such as different mosquitoes species (Aedes, Culex, Anopheles and others) and also midges, ticks and head lice.

It is a colorless and odorless oil with a good skin feel in final products. It is biodegradable.[2][3][4]

Chemistry

Ethyl butylacetylaminopropionate is a derivative of non-proteinogenic amino acid beta-alanine.[3]

IR3535 is produced by Merck KGaA in Europe.

Safety

Due to its chemical structure, IR3535® is very well tolerated by human skin, showing the best toxicological profile when compared to other molecules in the market, such as DEET, Picaridin and PMD.

It can be used by different group ages including adutls, sensitive skin types, elderly and infants including babies and toddlers.

Comparison of ethyl butylacetylaminopropionate and beta-alanine




References
  1. 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.
  2. Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
  3. 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (113509) Technical Document
  4. 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (IR3535) (113509) Fact Sheet
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