5-Caffeoylshikimic acid
[CAS# 73263-62-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 5-Caffeoylshikimic acid
• Synonyms: (3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
• Molecular Formula: C₁₆H₁₆O₈
• Molecular Weight: 336.29
• CAS Registry Number: 73263-62-4
• SMILES: C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 635.1±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 236.5±25.0 °C (Calc.)^*
• Index of refraction: 1.689 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Discovery and Applications

5-Caffeoylshikimic acid is a naturally occurring ester formed between caffeic acid and shikimic acid. Structurally, it consists of the phenolic compound caffeic acid linked via an ester bond to the hydroxyl group at the 5-position of shikimic acid, a cyclohexene-based acid involved in the biosynthesis of aromatic compounds in plants.

This compound is found in various plant species, particularly in those known for their rich phenolic content. It belongs to the class of hydroxycinnamic acid derivatives and is part of the broader group of phenolic esters that contribute to the plant's defense mechanisms and antioxidant properties. 5-Caffeoylshikimic acid is often isolated from plants used in traditional medicine or those studied for their health-promoting phytochemicals.

The biosynthesis of 5-caffeoylshikimic acid involves the esterification of caffeic acid, which is derived from the phenylpropanoid pathway, with shikimic acid, a key intermediate in the shikimate pathway. This biochemical pathway is crucial for the formation of aromatic amino acids and various secondary metabolites in plants.

In terms of application, 5-caffeoylshikimic acid has attracted attention due to its antioxidant properties. Phenolic compounds such as this are known to scavenge free radicals and may contribute to the reduction of oxidative stress in biological systems. This activity underlies the potential use of 5-caffeoylshikimic acid-rich plant extracts in nutraceuticals, functional foods, and cosmetic formulations aimed at protecting cells from oxidative damage.

Additionally, 5-caffeoylshikimic acid and related compounds have been studied for their anti-inflammatory, antimicrobial, and potential anticancer activities, though these effects have been primarily observed in in vitro studies. These bioactivities contribute to the pharmacological interest in plant extracts containing this compound.

From an analytical standpoint, 5-caffeoylshikimic acid can be isolated and quantified using chromatographic techniques such as high-performance liquid chromatography (HPLC), often coupled with mass spectrometry for structural confirmation. Its presence in plants serves as a biochemical marker for the quality and authenticity of certain herbal products.

In summary, 5-caffeoylshikimic acid is a plant-derived phenolic ester composed of caffeic acid and shikimic acid. It plays a role in plant metabolism and defense and is valued for its antioxidant and potential therapeutic properties. Its applications are mainly focused on health-related fields, leveraging its natural origin and bioactive characteristics.

References

1982. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor. Chemical and Pharmaceutical Bulletin, 30(9).
DOI: 10.1248/cpb.30.3219

2021. Natural Xanthine Oxidase Inhibitor 5-O-Caffeoylshikimic Acid Ameliorates Kidney Injury Caused by Hyperuricemia in Mice. Molecules, 26(23).
DOI: 10.3390/molecules26237307

2023. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS Pharmacology & Translational Science, 6(4).
DOI: 10.1021/acsptsci.2c00194