Ethyl butylacetylaminopropionate

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Ethyl butylacetylaminopropionate
IR3535
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
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 GHS07: Harmful
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

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]

Mechanism[edit]

Recent evidence with Anopheles gambiae mosquitoes suggests IR3535 does not activate olfactory receptors neurons, but instead functions to reduce the volatility of the odorants to which it is mixed.[4] By reducing odor volatility, IR3535 functions to "mask" the ability of volatile odorants on the skin to activate olfactory neurons and attract mosquitoes.[4]

Chemistry[edit]

Ethyl butylacetylaminopropionate and beta-alanine

Ethyl butylacetylaminopropionate is a derivative of beta-alanine.[5]

References[edit]

  1. ^ a b c d 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. ^ a b Afify, Ali; Betz, Joshua F.; Riabinina, Olena; Lahondère, Chloé; Potter, Christopher J. (2019). "Commonly Used Insect Repellents Hide Human Odors from Anopheles Mosquitoes". Current Biology. 29 (21): 3669–3680.e5. doi:10.1016/j.cub.2019.09.007. PMC 6832857. PMID 31630950.
  5. ^ EPA: Similarity to beta-alanine


External links[edit]