Chlorogenic acid
[CAS# 327-97-9]

Identification

• Classification: API >> Antipyretic analgesics >> Antipyretic and analgesic
• Name: Chlorogenic acid
• Synonyms: (1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid; 3-O-Caffeoylquinic acid; 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid
• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.31
• CAS Registry Number: 327-97-9
• EC Number: 206-325-6
• SMILES: C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*Melting point|205-209 ºC
• alpha: -36 º (c=1, H2O)
• Index of Refraction: 1.690, Calc.^*
• Boiling Point: 665.0±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 245.5±25.0 ºC, Calc.^*
• Water solubility: Soluble (hot water)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovory and Applicatios

Chlorogenic acid is a naturally occurring compound classified as a polyphenol and is primarily found in coffee beans, certain fruits, and vegetables. Its molecular formula is C16H18O9, and it is known for its antioxidant properties and potential health benefits. The discovery of chlorogenic acid can be traced back to the early 19th century when it was first isolated from green coffee beans. Researchers began to investigate its chemical structure and biological effects, leading to a better understanding of its significance in food science and health.

Chlorogenic acid is formed through the esterification of caffeic acid and quinic acid, resulting in a compound that exhibits various biological activities. The structure of chlorogenic acid consists of a caffeoyl group attached to a quinic acid backbone, which contributes to its distinctive properties. Over the years, studies have shown that chlorogenic acid possesses several beneficial effects, making it a subject of interest in nutritional research and pharmacology.

One of the most prominent applications of chlorogenic acid is in the food and beverage industry, particularly in coffee production. It contributes to the flavor and aroma of coffee, as well as its characteristic bitterness. The concentration of chlorogenic acid varies depending on the coffee bean variety and roasting process, with higher levels found in unroasted beans. Additionally, chlorogenic acid is responsible for some of the health benefits associated with coffee consumption, including antioxidant activity, anti-inflammatory effects, and potential weight management properties.

In the realm of health and wellness, chlorogenic acid has garnered attention for its potential therapeutic applications. Research suggests that it may help regulate blood sugar levels by inhibiting glucose absorption in the intestines, thereby aiding in the management of type 2 diabetes. Some studies indicate that chlorogenic acid may also enhance fat metabolism and promote weight loss, making it a popular ingredient in dietary supplements aimed at weight management.

Furthermore, chlorogenic acid exhibits antimicrobial properties, making it a potential candidate for use in food preservation. Its ability to inhibit the growth of certain bacteria and fungi can extend the shelf life of food products while maintaining their safety and quality. This antimicrobial effect has led to investigations into the incorporation of chlorogenic acid in various food matrices as a natural preservative.

Chlorogenic acid's antioxidant capacity is another area of interest, as it helps protect cells from oxidative stress and damage caused by free radicals. This property positions chlorogenic acid as a potential protective agent against various chronic diseases, including cardiovascular diseases and certain types of cancer. Ongoing research aims to explore its mechanisms of action and efficacy in promoting overall health.

In summary, chlorogenic acid is a versatile compound with significant implications in food science and health. From its discovery in coffee beans to its applications in weight management and food preservation, chlorogenic acid continues to be a focus of scientific research. Its potential health benefits and antioxidant properties make it an important subject of study in the quest for natural compounds that can contribute to human well-being.

References

2007. The phenylpropanoid micronutrient chlorogenic acid improves clinical rating scores in rabbits following multiple infarct ischemic strokes: Synergism with tissue plasminogen activator. Experimental Neurology, 205(2).
DOI: 10.1016/j.expneurol.2007.02.017

1969. o-Quinones formed in plant extracts. Their reactions with amino acids and peptides. The Biochemical journal, 112(5).
DOI: 10.1042/bj1120609

2024. Phytochemical characterization and evaluation of anti-inflammatory and anticancer activities of Cistus laurifolius originated propolis. European Food Research and Technology, Not applicable.
DOI: 10.1007/s00217-024-04624-7