Ethyl butylacetylaminopropionate

From Wikipedia, the free encyclopedia
(Redirected from Skin So Soft)
Jump to navigation Jump to search
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 Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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).

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]

Effectiveness

[edit | edit source]

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.[6][7]

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.[8][5] In areas with malaria, the NHS recommends 50% DEET or at least 30% DEET or 20% icaridin instead of IR3535.[9][10][11] 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.[12][13]

IR3535 also helps prevent bites from ticks that may transmit Lyme disease.[5]

Interactions

[edit | edit source]

Few if any studies have evaluated possible interactions when using IR3535 with sunscreens.[14]

Mechanism of action

[edit | edit source]

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.[15]

Chemistry

[edit | edit source]
File:Ethyl butylacetylaminopropionate and beta-alanine comparison.svg
Comparison of ethyl butylacetylaminopropionate and beta-alanine

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

Approval

[edit | edit source]

IR3535 is approved by several authorities around the world, including ECHA (Europe)[16] and the EPA (US)[17] where it is considered a biopesticide.

See also

[edit | edit source]

References

[edit | edit source]
  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. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  5. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  6. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  7. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  8. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  10. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  11. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  12. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  13. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  14. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  15. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  16. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  17. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
[edit | edit source]
Retrieved from "http://70.231.62.181/index.php?title=Ethyl_butylacetylaminopropionate&oldid=10014625"