Ethyl butylacetylaminopropionate

Ethyl butylacetylaminopropionate
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
CAS Number	52304-36-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	94028 ;
ECHA InfoCard	100.052.560
PubChem CID	104150;
UNII	65GQA237EH ;
CompTox Dashboard (EPA)	DTXSID9035753 ;
	show InChI
	show SMILES
Properties
Chemical formula	C11H21NO3
Molar mass	215.293 g·mol−1
Appearance	Colorless liquid
Odor	Almost odorless
Density	0.998 g/cm3 (at 20 °C)
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)	>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).
	(what is ?)
	Infobox references

Ethyl butylacetylaminopropionate (trade name IR3535) is an insect repellent which is applied topically to prevent bites and stings from mosquitos, ticks, and other insects.^[1] It is a colorless and almost odorless oil, has efficacy against a broad range of insects, and is reasonably biodegradable.^[2]^[3]^[4]

Chemistry[]

Ethyl butylacetylaminopropionate and beta-alanine

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

References[]

^ 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.
^ Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
^ Jump up to: ^a ^b 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

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

[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.

[:0-2] Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)

[:1-3] Jump up to: ^a ^b 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (113509) Technical Document

[:2-4] 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (IR3535) (113509) Fact Sheet

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[2]

[3]

[4]

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
CAS Number	52304-36-6^Y
3D model (JSmol)	Interactive image
ChemSpider	94028^Y
ECHA InfoCard	100.052.560
PubChem CID	104150
UNII	65GQA237EH^Y
CompTox Dashboard (EPA)	DTXSID9035753
show InChI InChI=1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3^Y Key: VZRKEAFHFMSHCD-UHFFFAOYSA-N^Y
show SMILES CCCCN(CCC(=O)OCC)C(=O)C
Properties
Chemical formula	C₁₁H₂₁NO₃
Molar mass	215.293 g·mol⁻¹
Appearance	Colorless liquid
Odor	Almost odorless
Density	0.998 g/cm³ (at 20 °C)
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)	>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).
Y (what is ^YN ?)
Infobox references