Revision as of 12:17, 23 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'StdInChI', 'StdInChIKey').← Previous edit | Latest revision as of 12:05, 4 April 2024 edit undoRiche Mark Iscala (talk | contribs)231 editsmNo edit summaryTag: Visual edit | ||
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{{Chembox | {{Chembox | ||
| Watchedfields = changed | |||
| verifiedrevid = 406153746 | |||
| verifiedrevid = 446308577 | |||
| ImageFile = Chemical Structure of IR3535.png | |||
| ImageFile = Ethyl butylacetylaminopropionate.svg | |||
| ImageSize = 260px | |||
| |
| ImageSize = 250px | ||
| ImageAlt = IR3535 | |||
| IUPACName = ethyl 3-propanoate | |||
| IUPACName = Ethyl ''N''-acetyl-''N''-butyl-β-alaninate | |||
| PIN = | |||
| PIN = Ethyl 3-(''N''-butylacetamido)propanoate | |||
| OtherNames = 3--aminopropionic acid, ethyl ester | |||
| |
| OtherNames = {{Unbulleted list | ||
| EBAAP | |||
| CASNo = 52304-36-6 | |||
| β-alanine, ''N''-acetyl-''N''-butyl-, ethyl ester | |||
| PubChem = 104150 | |||
| IR3535 | |||
| ChemSpiderID = 94028 | |||
| Insect Repellent 3535 | |||
| BAAPE | |||
}} | |||
|Section1={{Chembox Identifiers | |||
| CASNo_Ref = {{cascite|correct|??}} | |||
| CASNo = 52304-36-6 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| UNII = 65GQA237EH | |||
| PubChem = 104150 | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| ChemSpiderID = 94028 | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChI = 1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3 | | StdInChI = 1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3 | ||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChIKey = VZRKEAFHFMSHCD-UHFFFAOYSA-N | | StdInChIKey = VZRKEAFHFMSHCD-UHFFFAOYSA-N | ||
| SMILES = CCCCN(CCC(=O)OCC)C(=O)C}} | | SMILES = CCCCN(CCC(=O)OCC)C(=O)C}} | ||
| |
|Section2={{Chembox Properties | ||
| C=11 | H=21 | N=1 | O=3 | |||
| Formula = C<sub>11</sub>H<sub>21</sub>NO<sub>3</sub> | |||
| Appearance = Colorless liquid | |||
| MolarMass = 215.28934 | |||
| Odor = Almost odorless | |||
| Appearance = | |||
| |
| Density = 0.998 g/cm<sup>3</sup> (at 20 °C) | ||
| |
| MeltingPt = < -90 °C | ||
| |
| BoilingPt = 141 °C (decomposes) | ||
| LogP = 1.7 (at 23 °C) | |||
| Solubility = }} | |||
| Solubility = 70 g/L (at 20 °C) | |||
| Section3 = {{Chembox Hazards | |||
| SolubleOther = >250 g/L (at RT) | |||
| MainHazards = Biopesticide | |||
| Solvent = Acetone, ethyl acetate, dichloromethane, ''n''-heptane, methanol, ''p''-xylene | |||
| FlashPt = | |||
| Autoignition = }} | |||
}} | }} | ||
|Section3={{Chembox Hazards | |||
| FlashPtC = 159 | |||
| GHSPictograms = {{GHS exclamation mark}} | |||
| GHSSignalWord = '''Warning''' | |||
| HPhrases = {{H-phrases| 319}} | |||
| PPhrases = {{P-phrases| 280 | 305+351+338 | 337+313}} | |||
| LD50 = {{Unbulleted list | |||
| >5000 mg/kg (rat, oral) | |||
|10000 mg/kg (rate, dermal) | |||
|>5.1 mg/L (rat, inhalation)}} | |||
}} | |||
}} | |||
'''Ethyl butylacetylaminopropionate''' is an ] whose trade name is '''IR3535''' and was developed and commercialized by ] (Germany). It is a colorless and odorless oil with a good skin feel in final products, and it is ].<ref name=":0"></ref><ref name=":1"></ref><ref name=":2"></ref> | |||
Unlike ], IR3535 can dissolve some plastics and synthetic fabrics, except ] and ].<ref>{{cite web |title=Insect Repellent - FAQ |url=https://www.merckgroup.com/en/expertise/cosmetics/care-solutions/insect-repellent/faq.html |publisher=Merck |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230922130527/https://www.emdgroup.com/en/expertise/cosmetics/care-solutions/insect-repellent/faq.html |archive-date=22 September 2023 |url-status=live |quote=Like a number of other repellents, IR3535® is not compatible with certain synthetic materials.}}</ref><ref name="ewg2018">{{cite web |title=EWG’s 2018 Guide to Bug Repellents |url=https://www.ewg.org/consumer-guides/ewgs-2018-guide-bug-repellents |publisher=Environmental Working Group |access-date=9 August 2023 |date=17 July 2018 |archive-url=https://web.archive.org/web/20210410185511/https://www.ewg.org/consumer-guides/ewgs-2018-guide-bug-repellents |archive-date=10 April 2021 |url-status=live}}</ref><ref name="ncpc">{{cite web |title=Insect Repellents |url=https://www.poison.org/articles/insect-repellent |publisher=National Capital Poison Center |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230601091355/https://www.poison.org/articles/insect-repellent |archive-date=1 June 2023 |url-status=live |quote=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.}}</ref> | |||
'''IR3535''' is an insect repellent found in ] '''Skin So Soft''' line of topical insect repellents. ] is the registered trademark owner of IR3535 in the United States.<ref></ref> IR3535 is a synthetic ] that is additionally classified as '''biopesticide'''<ref></ref> by the ]. It was used in Europe 20 years prior to its registration with the EPA as an active ingredient in February 1999.<ref></ref> | |||
== Effectiveness == | |||
IR3535 is effective in repelling several different insects such as mosquitoes species and also ], ] and ]. It is as effective as ] against '']'' and '']'' mosquitoes, but may be less effective than DEET against '']'' mosquitoes, vectors of ].<ref name="jtm2010">{{Cite journal |vauthors=Goodyer LI, Croft AM, Frances SP, Hill N, Moore SJ, Onyango SP, Debboun M |display-authors=6 |date=1 May 2010 |title=Expert Review of the Evidence Base for Arthropod Bite Avoidance |url=https://academic.oup.com/jtm/article-lookup/doi/10.1111/j.1708-8305.2010.00402.x |journal=Journal of Travel Medicine |volume=17 |issue=3 |pages=182–192 |doi=10.1111/j.1708-8305.2010.00402.x |issn=1195-1982}}</ref><ref>{{Cite journal |last=Diaz |first=James H. |date=March 2016 |title=Chemical and Plant-Based Insect Repellents: Efficacy, Safety, and Toxicity |url=https://linkinghub.elsevier.com/retrieve/pii/S1080603215004342 |journal=Wilderness & Environmental Medicine |volume=27 |issue=1 |pages=153–163 |doi=10.1016/j.wem.2015.11.007|doi-access=free }}</ref> | |||
A 2013 review concluded that IR3535 is as effective as 20% ] against ''Anopheles'', citing that some studies reported possibly shorter protection of just 3.8 hours.<ref name="tmid2013">{{Cite journal |vauthors=Lupi E, Hatz C, Schlagenhauf P |date=November 2013 |title=The efficacy of repellents against Aedes, Anopheles, Culex and Ixodes spp. – A literature review |url=https://linkinghub.elsevier.com/retrieve/pii/S1477893913001737 |journal=Travel Medicine and Infectious Disease |volume=11 |issue=6 |pages=374–411 |doi=10.1016/j.tmaid.2013.10.005}}</ref><ref name="ncpc"/> In areas with malaria, the NHS recommends 50% DEET or at least 30% DEET or 20% ] instead of IR3535.<ref>{{cite web |title=Malaria |url=https://www.nhs.uk/conditions/malaria/ |publisher=NHS |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230730193653/https://www.nhs.uk/conditions/malaria/ |archive-date=30 July 2023 |quote=use insect repellent on your skin – make sure it's 50% DEET-based |url-status=live}}</ref><ref>{{cite web |title=Mosquito bite avoidance: advice for travellers |url=https://www.gov.uk/government/publications/mosquito-bite-avoidance-for-travellers/mosquito-bite-avoidance-advice-for-travellers--2 |publisher=Gov.uk |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230124113031/https://www.gov.uk/government/publications/mosquito-bite-avoidance-for-travellers/mosquito-bite-avoidance-advice-for-travellers--2 |archive-date=24 January 2023 |url-status=live |quote=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.}}</ref><ref>{{Cite web |last=Team |first=HPS Travel Health |title=Mosquito Bite Avoidance - Fit for Travel |url=https://www.fitfortravel.nhs.uk/advice/malaria/mosquito-bite-avoidance.aspx |access-date=2023-08-07 |website=Fit for Travel |archive-url=https://web.archive.org/web/20230807160632/https://www.fitfortravel.nhs.uk/advice/malaria/mosquito-bite-avoidance.aspx |archive-date=7 August 2023 |url-status=live |quote=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}}</ref> IR3535, among other repellents, is included in the ] (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.<ref>{{Cite news |date=2023-03-29 |title=Malaria |url=https://www.who.int/news-room/fact-sheets/detail/malaria |access-date=2023-09-29 |publisher=World Health Organization}}</ref><ref>{{cite book |date=2020 |title=International Travel and Health |url=https://www.who.int/publications/i/item/9789241580472 |chapter=Malaria |publisher=World Health Organization |isbn=978-92-4-158047-2 |access-date=2023-09-30 |chapter-url=https://cdn.who.int/media/docs/default-source/travel-and-health/9789241580472-eng-chapter-7.pdf}}</ref> | |||
IR3535 also helps prevent bites from ticks that may transmit ].<ref name="ncpc"/> | |||
== Adverse effects == | |||
IR3535 can irritate the eyes on contact.<ref name="ewg2018"/> | |||
== Interactions == | |||
Few if any studies have evaluated possible interactions when using IR3535 with sunscreens.<ref>{{cite web |title=Insect Repellents |url=http://npic.orst.edu/factsheets/repellents.html |publisher=National Pesticide Information Center |access-date=26 September 2023 |archive-url=https://web.archive.org/web/20230913011642/http://npic.orst.edu/factsheets/repellents.html |archive-date=13 September 2023 |date=February 2018 |url-status=live |quote=Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens.}}</ref> | |||
== Mechanism of action == | |||
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 ], ], ], ], ], among others.<ref>{{Cite journal|last=Lo|first=Wai Ling|last2=Mok|first2=Ka Leung|last3=Yu Pui Ming|first3=Stephanie Dorothy|date=2018-09-01|title=Which insect repellents should we choose? Implications from results of local market survey and review of current guidelines|url=https://doi.org/10.1177/1024907918773630|journal=Hong Kong Journal of Emergency Medicine|language=en|volume=25|issue=5|pages=272–280|doi=10.1177/1024907918773630|issn=1024-9079|doi-access=free}}</ref> | |||
== Chemistry == | == Chemistry == | ||
] | ] | ||
The structure of IR3535 is based on ]<ref></ref> and ].<ref></ref> and the EPA has classified IR3535 as a biochemical substance based on the fact that it is "functionally identical" to beta alanine: both repel insects and the end groups of IR3535 are not likely to contribute to toxicity. <ref></ref> | |||
IR3535 is a ] of non-proteinogenic amino acid ].<ref name=":1" /> | |||
{{clear-left}} | |||
== Approval == | |||
IR3535 is approved by several authorities around the world, including ] (Europe)<ref>{{cite web |author1=Belgium (competent authority) |title=Regulation (EU) 528/2012 evaluation of active substances / Assessment Report / Ethyl butylacetylaminopropionate / Product-type 19 (insect repellent) |url=https://echa.europa.eu/documents/10162/aaf5b78c-82ca-40a3-25a4-1cc4339c9407 |date=March 13, 2014}}</ref> and the ] (US)<ref>{{cite web |last1=Environmental Protection Agency |title=3--aminopropionic acid, ethyl ester (IR3535) Interim Registration Review Decision Case Number 6046 |url=https://www.regulations.gov/document/EPA-HQ-OPP-2014-0106-0009 |website=www.regulations.gov |date=Feb 3, 2020}}</ref> where it is considered a biopesticide. | |||
== See also == | == See also == | ||
* ] | * ] | ||
* ] | |||
* ] (PMD) | |||
* ], a ] ] that can be applied to clothing to help prevent bites | |||
:{{clear-left}} | |||
== References == | == References == | ||
{{Reflist}} | |||
<references/> | |||
== External links == | == External links == | ||
* {{cite journal | doi = 10.1603/0022-2585-39.6.895 | pmid = 12495189 | url = http://ddr.nal.usda.gov/bitstream/10113/6633/1/IND23332072.pdf | archive-url = https://web.archive.org/web/20110721072133/http://ddr.nal.usda.gov/bitstream/10113/6633/1/IND23332072.pdf | url-status = dead | archive-date = 2011-07-21 | title = Repellency of IR3535, KBR3023, para-menthane-3,8-diol, and DEET to Black Salt Marsh Mosquitoes (Diptera: Culicidae) in the Everglades National Park| journal = Journal of Medical Entomology| volume = 39| issue = 6| pages = 895–899| year = 2002| last1 = Barnard| first1 = Donald R.| last2 = Bernier| first2 = Ulrich R.| last3 = Posey| first3 = Kenneth H.| last4 = Xue| first4 = Rui-De| doi-access = free}} | |||
* | |||
* | * | ||
* | |||
* | |||
] | |||
{{DEFAULTSORT:Ir3535}} | |||
] | ] | ||
] | |||
] | |||
{{organic-compound-stub}} |
Latest revision as of 12:05, 4 April 2024
Names | |
---|---|
IUPAC name Ethyl N-acetyl-N-butyl-β-alaninate | |
Preferred IUPAC name Ethyl 3-(N-butylacetamido)propanoate | |
Other names
| |
Identifiers | |
CAS Number | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.052.560 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
Properties | |
Chemical formula | C11H21NO3 |
Molar mass | 215.293 g·mol |
Appearance | Colorless liquid |
Odor | Almost odorless |
Density | 0.998 g/cm (at 20 °C) |
Melting point | < -90 °C |
Boiling point | 141 °C (decomposes) |
Solubility in water | 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: | |
Pictograms | |
Signal word | Warning |
Hazard statements | H319 |
Precautionary statements | P280, P305+P351+P338, P337+P313 |
Flash point | 159 °C (318 °F; 432 K) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references |
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.
Unlike icaridin, IR3535 can dissolve some plastics and synthetic fabrics, except polyethylene and polypropylene.
Effectiveness
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.
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. In areas with malaria, the NHS recommends 50% DEET or at least 30% DEET or 20% icaridin instead of IR3535. 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.
IR3535 also helps prevent bites from ticks that may transmit Lyme disease.
Adverse effects
IR3535 can irritate the eyes on contact.
Interactions
Few if any studies have evaluated possible interactions when using IR3535 with sunscreens.
Mechanism of action
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.
Chemistry
IR3535 is a derivative of non-proteinogenic amino acid beta-alanine.
Approval
IR3535 is approved by several authorities around the world, including ECHA (Europe) and the EPA (US) where it is considered a biopesticide.
See also
- DEET
- Icaridin
- p-Menthane-3,8-diol (PMD)
- Permethrin, a pyrethroid insecticide that can be applied to clothing to help prevent bites
References
- Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
- ^ 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (113509) Technical Document
- 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (IR3535) (113509) Fact Sheet
- "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.
- ^ "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.
- ^ "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.
- 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.
- 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.
- 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.
- "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
- "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.
- 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
- "Malaria". World Health Organization. 2023-03-29. Retrieved 2023-09-29.
- "Malaria" (PDF). International Travel and Health. World Health Organization. 2020. ISBN 978-92-4-158047-2. Retrieved 2023-09-30.
- "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.
- 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.
- Belgium (competent authority) (March 13, 2014). "Regulation (EU) 528/2012 evaluation of active substances / Assessment Report / Ethyl butylacetylaminopropionate / Product-type 19 (insect repellent)".
- 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.
External links
- 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