Piperine
[CAS# 94-62-2]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Cyclic hydrocarbon
• Name: Piperine
• Synonyms: (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.34
• CAS Registry Number: 94-62-2
• EC Number: 202-348-0
• FEMA: 2909
• SMILES: C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3

Properties

• Water solubility: 40 mg/L (18 °C) (Expl.)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 131-135 °C (Expl.)
• Index of Refraction: 1.615, Calc.^*
• Boiling Point: 498.5±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 255.3±27.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H300-H412
• Safety Statements: P264-P270-P273-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Piperine, with the chemical formula C17H19NO3, is an alkaloid compound that occurs naturally in black pepper (Piper nigrum) and long pepper (Piper longum). It is the substance responsible for the characteristic spicy, pungent flavor of pepper, and has been utilized for centuries in various traditional medicine practices due to its broad pharmacological properties. The chemical structure of piperine includes a pyridine ring and a long side chain, making it an interesting subject for scientific research in both food chemistry and pharmacology.

The discovery of piperine dates back to the 19th century when it was first isolated from black pepper by the German chemist Hans J. C. von Liebig in 1820. Since then, piperine has been the subject of extensive study, with researchers exploring its chemical properties and potential health benefits. Its presence in black pepper, one of the most widely consumed spices globally, has made it a readily accessible compound, and its role in enhancing the bioavailability of other substances has garnered significant interest in modern science.

Piperine has been studied for its diverse range of biological activities, which have led to its application in various industries, particularly in medicine and wellness. One of the most notable applications of piperine is in enhancing the absorption and bioavailability of various drugs and nutrients. Piperine is known to inhibit certain enzymes in the liver and intestines, particularly cytochrome P450 enzymes, which are involved in the metabolism of drugs. This inhibition slows the breakdown of drugs in the body, allowing them to remain active for longer periods and thus increasing their effectiveness. As a result, piperine is often included in supplements and pharmaceutical formulations to improve the efficacy of other active compounds, such as curcumin, resveratrol, and certain vitamins.

In addition to its role as a bioavailability enhancer, piperine has demonstrated a range of pharmacological properties. It has been studied for its anti-inflammatory, antioxidant, and antimicrobial effects, which make it a potential therapeutic agent in the treatment of various health conditions. For instance, piperine has been shown to have significant anti-inflammatory effects in preclinical studies, which could make it useful in the management of chronic inflammatory diseases, such as arthritis. Furthermore, its antioxidant properties have led to its investigation as a potential agent in preventing oxidative stress-related conditions, including cardiovascular diseases and cancer.

Piperine also exhibits analgesic and neuroprotective effects, which have contributed to its exploration in pain management and neurodegenerative disease treatment. Studies have indicated that piperine may act as a mild analgesic, offering relief from pain through mechanisms similar to those of nonsteroidal anti-inflammatory drugs (NSAIDs). Its neuroprotective effects have sparked interest in its potential use in treating conditions like Alzheimer's disease, as it may help in reducing the accumulation of beta-amyloid plaques and protecting neuronal cells from oxidative damage.

Apart from its medicinal applications, piperine has been utilized in the food industry as a flavoring agent and preservative. Its pungency and distinct aroma make it a key ingredient in many spice blends and seasonings. Additionally, its antimicrobial properties help in inhibiting the growth of foodborne pathogens, contributing to its role as a natural preservative in food products.

The cosmetic industry has also found uses for piperine, particularly in skin care products. Due to its ability to increase the absorption of active ingredients through the skin, piperine is sometimes incorporated into topical formulations aimed at enhancing the effectiveness of other skin care compounds, such as retinoids or antioxidants.

In conclusion, piperine is a naturally occurring alkaloid with significant biological activity and a broad range of applications across various industries. Its discovery in black pepper has led to its use not only as a flavoring agent but also as a therapeutic compound with potential benefits in medicine, nutrition, and cosmetics. Continued research into its mechanisms of action and therapeutic potential may further expand its applications and reveal new ways to harness its beneficial properties.

References

2024. Design, Synthesis, and Antiproliferative Evaluation of Piperine Derivatives. Russian Journal of Organic Chemistry, 60(7).
DOI: 10.1134/s1070428024070212

2018. Increased Oral Bioavailability of Piper nigrum Nanosuspension. Planta Medica, 84(15).
DOI: 10.1055/a-0759-2208

2015. Piperine: Bioactivities and Structural Modifications. Mini-Reviews in Medicinal Chemistry, 15(2).
DOI: 10.2174/1389557515666150101100509