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Basicity of Heterocyclic Aromatic Amines

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
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Acid Halides to Esters: Alcoholysis

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

Acidity and Basicity of Alcohols and Phenols

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
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Updated: Jan 16, 2026

Quantification of Humic and Fulvic Acids in Humate Ores, DOC, Humified Materials and Humic Substance-Containing Commercial Products

Quantification of Humic and Fulvic Acids in Humate Ores, DOC, Humified Materials and Humic Substance-Containing Commercial Products

Published on: March 18, 2022

Humulupones A-F, Bitter Acid Derivatives from Humulus lupulus.

Biao Sun¹, Zi-Wei Li¹, Man Lin²

¹State Key Laboratory of Bioactive Molecules and Druggability Assessment, & Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou 510632, P. R. China.

Organic Letters

|September 25, 2025

Summary

This summary is machine-generated.

Six new bitter acid derivatives, humulupones A-F, were isolated from Humulus lupulus. These compounds exhibit novel skeletons, anti-inflammatory, and antiviral activities.

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Published on: November 30, 2022

Area of Science:

Natural Product Chemistry
Organic Chemistry
Pharmacology

Background:

Humulus lupulus (hops) is a source of diverse chemical compounds.
Bitter acids are a significant class of hop constituents with various biological activities.

Purpose of the Study:

To isolate and characterize new bitter acid derivatives from Humulus lupulus.
To investigate the anti-inflammatory and antiviral properties of the isolated compounds.

Main Methods:

Isolation and purification of compounds using chromatographic techniques.
Structure elucidation through comprehensive spectroscopic analysis (NMR, MS) and X-ray diffraction.
Biological evaluation using zebrafish inflammatory model and herpes simplex virus type-1 assays.

Main Results:

Six new bitter acid derivatives, humulupones A-F (1-6), were identified, featuring unprecedented pentacyclic and tricyclic ring systems.
Compounds 1-4 possessed a novel 6/6/6/6/6 pentacyclic skeleton, while compounds 5-6 displayed a unique 6/5/6 tricyclic system.
Compounds 1, 3, 4, and 6 demonstrated significant anti-inflammatory effects, and compounds 1-4 exhibited potent antiviral activity against herpes simplex virus type-1.

Conclusions:

The study successfully identified novel chemical structures from Humulus lupulus.
The isolated humulupones possess promising anti-inflammatory and antiviral properties, warranting further investigation for therapeutic potential.