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Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

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Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
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Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

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Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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Structures of Aldehydes and Ketones01:04

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Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the...
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Spectroscopy of Carboxylic Acid Derivatives01:26

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Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and...
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Naturally Occurring Cinnamic Acid Sugar Ester Derivatives.

Yuxin Tian1, Weirui Liu2, Yi Lu3

  • 1School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. tianyuxin1216@163.com.

Molecules (Basel, Switzerland)
|October 27, 2016
PubMed
Summary

Cinnamic acid sugar ester derivatives (CASEDs) show promising antidepressant and neuroprotective effects. Research highlights their natural origins and potential as novel therapeutic compounds.

Keywords:
cinnamic acid sugar ester derivativespharmacological activityphytochemistrytraditional Chinese medicine

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Medicinal Chemistry

Background:

  • Cinnamic acid sugar ester derivatives (CASEDs) are natural products with phenylacrylic moieties linked to glycosyl skeletons.
  • These compounds exhibit significant antidepressant and neuroprotective activities.
  • 3',6-disinapoylsucrose, a key component of Traditional Chinese Medicine (TCM) Yuanzhi, is a notable example with molecular-level antidepressant effects.

Purpose of the Study:

  • To provide a comprehensive overview of cinnamic acid sugar ester derivatives (CASEDs).
  • To discuss their isolation, distribution, chemical structures, properties, and pharmacological activities.
  • To serve as a reference for natural product researchers and highlight the potential of these compounds.

Main Methods:

  • Literature review and systematic analysis of existing research on CASEDs.
  • Discussion of isolation techniques and structural characterization methods.
  • Compilation of data on distribution in plant families, particularly *Polygalaceae*.

Main Results:

  • CASEDs are widely distributed in nature, with over a third found in the *Polygalaceae* family.
  • Various CASEDs demonstrate calming, anti-depressant, and neuroprotective properties.
  • 3',6-disinapoylsucrose is identified as a significant lead compound for drug development.

Conclusions:

  • Cinnamic acid sugar ester derivatives (CASEDs) represent a valuable class of natural products with significant therapeutic potential.
  • Further research into their isolation, structure-activity relationships, and pharmacological mechanisms is warranted.
  • These compounds hold promise for the development of new treatments for neurological and psychiatric disorders.