Ethyl butylacetylaminopropionate

Ethyl butylacetylaminopropionate (trade name IR3535) is an insect repellent. As ethyl butylacetylaminopropionate is solely a repellent, it has no killing action and does not give rise to selection pressure or development of resistance.[1] It is a colorless and almost odorless oil and is intended to be applied to the skin of humans and animals.[1][2] It has a broad efficacy against various insects like mosquitoes, ticks, lice, and other bugs.[1][2][3] Ethyl butylacetylaminopropionate is safe for use on infants, pregnant and breastfeeding women. It is biodegradable and completely degraded in the environment within a very short time.[1]

Ethyl butylacetylaminopropionate
Names
IUPAC name
Ethyl N-acetyl-N-butyl-β-alaninate
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
Properties
C11H21NO3
Molar mass 215.293 g·mol−1
Appearance Colorless liquid
Odor Almost odorless
Density 0.998 g/cm3 (at 20 °C)
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
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):
  • >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).
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Infobox references

Chemistry
Ethyl butylacetylaminopropionate and beta-alanine

Ethyl butylacetylaminopropionate is a derivative of beta-alanine.[4]

References
  1. Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
  2. 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. EPA: Similarity to beta-alanine
    • 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" (PDF). Journal of Medical Entomology. 39 (6): 895–899. doi:10.1603/0022-2585-39.6.895. PMID 12495189. Archived from the original (PDF) on 2011-07-21.
    • Tick Bite Prevention & the Use of Insect Repellents
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