Butyl cinnamate

• CAT Number: I023862
• CAS Number: 538-65-8
• Molecular Formula: C13H16O2
• Molecular Weight: 204.27
• Purity: 98%
• Synonyms: NSC 71966; NSC71966; NSC-71966; Butyl cinnamate
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: 2-8°C
• IUPAC Name: 2-Propenoic acid, 3-phenyl-, butyl ester
• InChI: InChI=1S/C13H16O2/c1-2-3-11-15-13(14)10-9-12-7-5-4-6-8-12/h4-10H,2-3,11H2,1H3/b10-9+
• InChIKey: OHHIVLJVBNCSHV-MDZDMXLPSA-N
• SMILES: O=C(OCCCC)/C=C/C1=CC=CC=C1

Butyl cinnamate（Cat No.:I023862） is a compound known to have mosquito-repellent properties. It is derived from cinnamic acid and possesses a pleasant fragrance. Butyl cinnamate is often used in formulations of mosquito repellent products due to its ability to deter mosquitoes and other biting insects. It works by creating a scent barrier that masks the attractants and disrupts the mosquito’s ability to locate and feed on human hosts. This makes butyl cinnamate a valuable ingredient in mosquito repellent formulations for personal protection against mosquito bites.

Reference

1: Kröber T, Koussis K, Bourquin M, Tsitoura P, Konstantopoulou M, Awolola TS, Dani FR, Qiao H, Pelosi P, Iatrou K, Guerin PM. Odorant-binding protein-based identification of natural spatial repellents for the African malaria mosquito Anopheles gambiae. Insect Biochem Mol Biol. 2018 May;96:36-50. doi: 10.1016/j.ibmb.2018.03.008. Epub 2018 Apr 12. PubMed PMID: 29656020.
2: Kakarla L, Katragadda SB, Tiwari AK, Kotamraju KS, Madhusudana K, Kumar DA, Botlagunta M. Free radical scavenging, α-glucosidase inhibitory and anti-inflammatory constituents from Indian sedges, Cyperus scariosus R.Br and Cyperus rotundus L. Pharmacogn Mag. 2016 Jul;12(Suppl 4):S488-S496. PubMed PMID: 27761080; PubMed Central PMCID: PMC5068129.
3: Jakovetić SM, Jugović BZ, Gvozdenović MM, Bezbradica DI, Antov MG, Mijin DZ, Knežević-Jugović ZD. Synthesis of aliphatic esters of cinnamic acid as potential lipophilic antioxidants catalyzed by lipase B from Candida antarctica. Appl Biochem Biotechnol. 2013 Aug;170(7):1560-73. doi: 10.1007/s12010-013-0294-z. Epub 2013 May 25. PubMed PMID: 23703579.
4: Bariamis SE, Marin M, Athanassopoulos CM, Kontogiorgis C, Tsimali Z, Papaioannou D, Sindona G, Romeo G, Avgoustakis K, Hadjipavlou-Litina D. Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives. Eur J Med Chem. 2013 Feb;60:155-69. doi: 10.1016/j.ejmech.2012.11.043. Epub 2012 Dec 7. PubMed PMID: 23291118.
5: Peh GR, Kantchev EA, Zhang C, Ying JY. N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine: a highly active, practical and versatile catalyst for the Heck-Mizoroki reaction. Org Biomol Chem. 2009 May 21;7(10):2110-9. doi: 10.1039/b821892g. Epub 2009 Mar 26. PubMed PMID: 19421449.
6: Koutsaplis M, Andrews PC, Bull SD, Duggan PJ, Fraser BH, Jensen P. A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres. Chem Commun (Camb). 2007 Sep 14;(34):3580-2. PubMed PMID: 18080550.
7: Bhatia SP, Wellington GA, Cocchiara J, Lalko J, Letizia CS, Api AM. Fragrance material review on butyl cinnamate. Food Chem Toxicol. 2007;45 Suppl 1:S49-52. Epub 2007 Sep 14. Review. PubMed PMID: 18037219.
8: Bhatia SP, Wellington GA, Cocchiara J, Lalko J, Letizia CS, Api AM. Fragrance material review on isobutyl cinnamate. Food Chem Toxicol. 2007;45 Suppl 1:S102-5. Epub 2007 Sep 15. Review. PubMed PMID: 18036714.
9: Ziolo J, Chrapec J, Rzoska SJ. Critical behavior of the isotropic-smectic-A transition in p-decyloxy-benzylidene-p-amino-2-methyl-butyl-cinnamate studied by the nonlinear dielectric effect method. Phys Rev A Gen Phys. 1989 Jul 1;40(1):448-450. PubMed PMID: 9901911.
10: Dumrongrattana S, Huang CC. Polarization and tilt-angle measurements near the smectic-A-chiral-smectic-C transition of p-(n-decyloxybenzylidene)-p-amino-(2-methyl-butyl)cinnamate (DOBAMBC). Phys Rev Lett. 1986 Feb 3;56(5):464-467. PubMed PMID: 10033199.
11: CAVIER R, JAMMET ML, BISMUT A. [Treatment of oxyuriasis by N-butyl cinnamate]. Presse Med. 1957 Jan 16;65(5):91. French. PubMed PMID: 13420017.
12: CAVIER R, CHASLOT M. [Research on the anthelmintic properties of various derivatives of the cinnamic series. II. Pharmacological study of n-butyl cinnamate]. Ann Pharm Fr. 1956 May;14(5):370-3. French. PubMed PMID: 13373139.