Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Acidity and Basicity of Alcohols and Phenols

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

The Small x Assumption

The Small x Assumption

If a reaction has a small equilibrium constant, the equilibrium position favors the reactants. In such reactions, a negligible change in concentration may occur if the initial concentrations of reactants are high and the Kc value is small. In such circumstances, the equilibrium concentration is approximately equal to its initial concentration. This estimation can be used to simplify the equilibrium calculations by assuming that some equilibrium concentrations are equal to the initial...

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

Structure and Nomenclature of Alcohols and Phenols

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Upcycled Cocoa Pod Husk: A Sustainable Source of Phenol and Polyphenol Ingredients for Skin Hydration, Whitening, and Anti-Aging.

Life (Basel, Switzerland)·2025

Same author

The potentiality of isoflavones from <i>Derris robusta</i> (DC.) Benth. against α-glucosidase.

Physical chemistry chemical physics : PCCP·2024

Same author

Potential of Arabica Coffee Beans from Northern Thailand: Exploring Antidiabetic Metabolites through Liquid Chromatography with Tandem Mass Spectrometry (LC-MS/MS) Metabolomic Profiling across Diverse Postharvest Processing Techniques.

Foods (Basel, Switzerland)·2023

Same author

Derrisrobustones A-D, isoflavones from the twig extract of Derris robusta (DC.) Benth. and their α-glucosidase inhibitory activity.

Phytochemistry·2022

Same author

Pulchelloid A, a sesquiterpene lactone from the Canadian prairie plant Gaillardia aristata inhibits mitosis in human cells.

Molecular biology reports·2021

Same author

Spirosteroids and α-glucosidase inhibitory norlignans from Asparagus racemosus Willd. roots.

Phytochemistry·2020

Search research articles

Related Experiment Video

Updated: May 22, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Absolute configuration of xerophenone A.

Hoong-Kun Fun, Cholpisut Tantapakul, Surat Laphookhieo

Acta Crystallographica. Section E, Structure Reports Online

|May 17, 2012

Summary

Xerophenone A, a novel rearranged benzophenone from Garcinia propinqua, has its absolute configuration and molecular structure elucidated. Its crystal packing reveals intricate intermolecular interactions.

More Related Videos

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Related Experiment Videos

Last Updated: May 22, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Area of Science:

Natural Product Chemistry
Organic Chemistry
Crystallography

Background:

Garcinia propinqua twigs are a source of unique natural compounds.
Rearranged benzophenones represent a class of molecules with potential biological activities.

Purpose of the Study:

To isolate and characterize xerophenone A, a novel rearranged benzophenone.
To determine the absolute configuration and detailed molecular structure of xerophenone A.
To investigate the crystal structure and intermolecular interactions of xerophenone A.

Main Methods:

Isolation and purification of xerophenone A from Garcinia propinqua.
X-ray crystallography for absolute configuration determination (Flack parameter refinement) and structural analysis.
Analysis of molecular conformations and intermolecular interactions (hydrogen bonding, C-H···O, C···O, C-H···π).

Main Results:

Xerophenone A, C(33)H(42)O(5), was isolated and its structure elucidated.
The absolute configuration of xerophenone A was determined as (1R,3R,4R,6S,8E,10R).
Crystal structure analysis revealed specific ring conformations, substituent disorder, and intermolecular interactions including O-H⋯O, C-H⋯O, and C⋯O contacts.

Conclusions:

The study successfully characterized the novel rearranged benzophenone, xerophenone A.
The detailed structural and stereochemical information provides a foundation for further investigation of its properties.
The crystal packing analysis offers insights into the solid-state behavior of this natural product.