Icaridin
[CAS# 119515-38-7]

Identification

• Classification: API >> Other chemicals
• Name: Icaridin
• Synonyms: Picaridin; sec-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate
• Molecular Formula: C₁₂H₂₃NO₃
• Molecular Weight: 229.32
• CAS Registry Number: 119515-38-7 (658051-75-3)
• EC Number: 423-210-8
• SMILES: CCC(C)OC(=O)N1CCCCC1CCO

Properties

• Density: 1.0±0.1 g/mL, Calc.^*
• Index of Refraction: 1.478, Calc.^*
• Boiling Point: 330.9±15.0 °C (760 mmHg), Calc.^*
• Flash Point: 153.9±20.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Icaridin, also known as picaridin, is a synthetic compound used primarily as an insect repellent. It was developed by Bayer in the 1980s as an alternative to DEET, with a chemical structure based on natural compounds found in the black pepper plant (Piperaceae family). It is a member of the piperidine chemical class and is known for its effectiveness in repelling a wide range of insects, including mosquitoes, ticks, and flies.

Icaridin is widely used in personal insect repellents due to its low toxicity, non-greasy feel, and lack of strong odor. It is effective in providing long-lasting protection against insect bites and has been approved for use in various formulations, including sprays, lotions, and wipes. Studies have shown that icaridin exhibits comparable or superior efficacy to DEET while being less irritating to the skin and having a lower potential for adverse effects.

The compound is recommended by the World Health Organization (WHO) and the Centers for Disease Control and Prevention (CDC) for protection against vector-borne diseases such as malaria, dengue, and Zika virus. It is used in both consumer and military applications as part of integrated vector control strategies.

Icaridin does not readily degrade plastics or synthetic materials, which is an advantage over DEET in certain applications. Its environmental profile indicates low toxicity to aquatic organisms and a minimal impact on ecosystems when used as directed. Due to its broad-spectrum efficacy and safety profile, icaridin continues to be a widely used active ingredient in insect repellent formulations worldwide.

References

1999. The conduct of a two-generation reproductive toxicity study via dermal exposure in the Sprague-Dawley rat--a case study with KBR 3023 (a prospective insect repellent). Reproductive toxicology (Elmsford, N.Y.).
DOI: 10.1016/s0890-6238(99)00008-8

2002. Field Evaluation of Repellent Formulations Against Daytime and Nighttime Biting Mosquitoes in a Tropical Rainforest in Northern Australia. Journal of Medical Entomology.
DOI: 10.1603/0022-2585-39.3.541

2024. Plant based and synthetic products as mosquito repellents: effects, target sites and their mechanism of action on mosquitoes. International Journal of Tropical Insect Science.
DOI: 10.1007/s42690-024-01329-y