Piperinic acid ethyl ester
[CAS# 56019-71-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Other carboxylic acid esters
• Name: Piperinic acid ethyl ester
• Synonyms: ethyl (2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoate
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26
• CAS Registry Number: 56019-71-7
• SMILES: CCOC(=O)/C=C/C=C/C1=CC2=C(C=C1)OCO2

Properties

• Solubility: Practically insoluble (0.032 g/L) (25 ºC), Calc.^*
• Density: 1.202±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.586, Calc.^*
• Melting point: 76-77 ºC (ethyl ether hexane )^**
• Boiling Point: 389.8±21.0 ºC (760 mmHg), Calc.^*
• Flash Point: 173.7±22.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Lee, Seung Ho; Heterocyclic Communications 2005, V11(5), P407-410.

Discovory and Applicatios

Piperinic acid ethyl ester, also known as ethyl piperate, was first discovered through chemical synthesis and research in the field of organic chemistry. It is derived from piperinic acid, which is found in black pepper, and is synthesized by esterification of piperinic acid with ethanol. This compound's discovery dates back to the late 20th century, with its structure confirmed through spectroscopic analysis and chemical characterization techniques. Piperinic acid ethyl ester's unique chemical properties and potential applications have since garnered significant interest in various industries.

Piperinic acid ethyl ester is utilized in the flavor and fragrance industry for its spicy and peppery aroma. It is used in the formulation of perfumes, colognes, and flavorings to impart a characteristic black pepper scent.

This compound finds applications in pharmaceuticals as an active ingredient in pain-relieving creams and ointments. Its potential analgesic properties make it suitable for topical formulations targeting muscle and joint pain.

Piperinic acid ethyl ester is used as a flavoring agent in the food industry, particularly in savory dishes and snacks. It enhances the taste profile of various food products, providing a mild spicy flavor reminiscent of black pepper.

In cosmetics, this compound is incorporated into skincare products for its purported antioxidant and anti-inflammatory properties. It is believed to help soothe irritated skin and reduce redness, making it a valuable ingredient in skincare formulations.

Piperinic acid ethyl ester is studied for its potential therapeutic properties, including its antimicrobial and anti-inflammatory effects. Researchers are exploring its applications in drug discovery and development for treating various ailments.

References

2012. Synthesis and inhibitory effect of piperine derivates on monoamine oxidase. Bioorganic & Medicinal Chemistry Letters, 22(9).
DOI: 10.1016/j.bmcl.2012.02.090

2011. Contribution of Carboxylesterase in Hamster to the Intestinal First-Pass Loss and Low Bioavailability of Ethyl Piperate, an Effective Lipid-Lowering Drug Candidate. Drug Metabolism and Disposition, 39(5).
DOI: 10.1124/dmd.110.037614