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sec-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

Product Namesec-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate
CAS119515-38-7
MFC12H23NO3
MW229.32
EINECS423-210-8
MOL File119515-38-7.mol

Chemical Properties

Melting point	<-170°
Boiling point	2800C
Density	d20 1.07
refractive index	nD20 1.4717
Flash point	142°C
storage temp.	Sealed in dry,2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Oil
pka	15.15±0.10(Predicted)
color	Colourless
Henry's Law Constant	3.3×10⁵ mol/(m³Pa) at 25℃, HSDB (2015)
Cosmetics Ingredients Functions	ANTIMICROBIAL
InChI	InChI=1S/C12H23NO3/c1-3-10(2)16-12(15)13-8-5-4-6-11(13)7-9-14/h10-11,14H,3-9H2,1-2H3
InChIKey	QLHULAHOXSSASE-UHFFFAOYSA-N
SMILES	N1(C(OC(C)CC)=O)CCCCC1CCO
CAS DataBase Reference	119515-38-7
EPA Substance Registry System	Icaridin (119515-38-7)

Safety Information

Hazardous Substances Data	119515-38-7(Hazardous Substances Data)
Toxicity	LD50 in rats (mg/kg): 4743 orally; >2000 dermally (Yap); LC50 in rainbow trout (96 hr): 173 mg/l; in bobwhite quail (5 day diet): >5000 ppm a.i. in diet (WHO).

Usage And Synthesis

Description

Picaridin is an insect repellent. It inhibits A. aegypti odorant receptor 2 (AaOR2) or AaOR8 in the presence of their odorant activators, indole and octenol, respectively, expressed in Xenopus oocytes (IC₅₀s = 1,452 and 1,911 μM, respectively). Picaridin reduces the number of entries into a food chamber by female D. melanogaster in an olfactory-based choice assay. It acts synergistically with the non-pyrethroid insecticide pyrimiphos methyl to increase mortality of A. gambiae and reduce blood feeding when used at a concentration of 10 g/m² on nets surrounding guinea pig cages. Formulations containing picaridin have been used as insect repellents against flies, mosquitoes, chiggers, ticks, and fleas.

Chemical Properties

Colorless Liquid

Uses

Insect repellent.

Uses

Acts on certain olfactory receptor cell types to reduce the activating or attracting effect of odor sources.Insect repellent.

Definition

ChEBI: Butan-2-yl 2-(2-hydroxyethyl)piperidine-1-carboxylate is a carboxylic acid and a member of piperidines.

Production Methods

Commercial production of icaridin involves a highly optimised chemical synthesis process developed to meet global demand for safe and effective insect repellents. The active ingredient is a piperidine derivative, and its synthesis typically starts with cyclohexane derivatives, which undergo a series of reactions including chlorination, etherification, and nitrile formation to build the final molecular structure.

Hazard

A reproductive hazard.

Mechanism of action

Topically applied, repellent. Odorant receptor. It has been proposed that icaridin may bind to odorant binding protein 1 (AgamOBP1).

References

[1] JONATHAN D BOHBOT Joseph C D. Insect repellents: modulators of mosquito odorant receptor activity.[J]. PLoS ONE, 2010: e12138. DOI: 10.1371/journal.pone.0012138
[2] ZAINULABEUDDIN SYED. Generic insect repellent detector from the fruit fly Drosophila melanogaster.[J]. PLoS ONE, 2011: e17705. DOI: 10.1371/journal.pone.0017705
[3] CéDRIC PENNETIER. Synergy between repellents and non-pyrethroid insecticides strongly extends the efficacy of treated nets against Anopheles gambiae.[J]. ACS Applied Bio Materials, 2007: 38. DOI: 10.1186/1475-2875-6-38

Pesticide Type

Insecticide; Repellent; Veterinary substance

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