Product name: 2,4-Dihydroxyacetophenone
Synonym name:
Catalogue No.: SBP00273
Cas No.: 89-84-9
Formula: C8H8O3
Mol Weight: 152.149
Botanical Source:
Physical Description: Powder
Type of Compound: Phenols
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.
For Reference Standard and R&D, Not for Human Use Directly.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
57.5300
1.4250
1.1864
3.6812
3.9812
22.0008
Low
65.6163
1.8876
Yes
No
Yes
No
Yes
No
0.6
Yes
No
Yes
No
2,4-Dihydroxyacetophenone (abbreviated as 2,4-DHAP) is an important natural compound belonging to the acetophenone compounds, with hydroxyl substituents at the 2' and 4' positions of the benzene ring in the molecule. As a derivative of resorcinol, 2,4-DHAP has attracted widespread attention in the field of natural product pharmacology due to its unique chemical structure and bioactivity. In recent years, as the issue of antimicrobial resistance has become increasingly severe, natural products as potential resources for new antimicrobial drugs have been re-examined. 2,4-DHAP has gradually become a research hotspot due to its significant antibacterial activity and good safety.
This review aims to systematically summarize the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of 2,4-dihydroxyacetophenone, druggability evaluation and pharmacokinetic characteristics, and, combined with current research progress, explore its clinical application prospects and directions, providing theoretical basis and research reference for subsequent drug development and clinical translation.
2,4-Dihydroxyacetophenone has the chemical formula C8H8O3 and a molecular weight of 152.1490. Its structural feature is that the benzene ring is connected to hydroxyl groups at the 2' and 4' positions, and the benzene ring is connected to the acetone group via the acetone side chain, forming a typical dihydroxyphenylacetone backbone. This structure endows it with strong polarity and a certain degree of hydrophilicity, while the presence of hydroxyl groups gives it excellent ability to serve as both hydrogen bond donor and acceptor, facilitating binding with biological macromolecules.
In terms of physicochemical properties, the LogP value of 2,4-DHAP is 1.4250, indicating moderate lipid solubility, which facilitates membrane penetration without excessive hydrophobicity and affecting solubility. The topological pole surface area (TPSA) is 57.53 Ų, indicating moderate polarity and possibly supporting good bioavailability. Its water solubility is 3.6812, indicating a certain solubility in the aqueous phase, making it easy to absorb and distribute in the body. Low blood-brain barrier permeability suggests that this compound has difficulty entering the central nervous system, reducing the risk of central toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames trial scored 0.6, indicating a low genotoxicity risk and a solid safety foundation.
2,4-Dihydroxyacetophenone is widely present in various plants, especially as a secondary metabolite of certain medicinal plants. Its natural sources mainly include the roots, stems, and leaves of Rutaceae, Fabaceae, and certain woody plants. Plants synthesize this compound through the phenylalanine metabolic pathway, which is part of plant defense mechanisms and exerts biological functions such as antibacterial and antioxidant properties.
Common extraction methods include solvent extraction, ultrasound-assisted extraction, microwave-assisted extraction, and others. Generally, polar organic solvents such as methanol, ethanol, or ethyl acetate are used for extraction and combine liquid-liquid partitioning and chromatographic purification steps (such as column chromatography and preparative high-performance liquid chromatography) to obtain high-purity 2,4-DHAP. In recent years, the application of green extraction technologies, such as supercritical CO2 extraction and natural deep co-solvent extraction, has gradually been introduced to improve extraction efficiency and environmental friendliness.
Pharmacological activity studies of 2,4-dihydroxyacetophenone mainly focus on its antibacterial effects, but its antioxidant, anti-inflammatory, and potential antitumor activities are also gradually being revealed.
2,4-DHAP exhibits inhibitory effects on various bacteria and fungi, especially showing significant inhibitory effects against Gram-positive bacteria and some Gram-negative bacteria. Its antibacterial spectrum includes Staphylococcus aureus, Streptococcus, Streptococcus pneumoniae, and some resistant strains. Research shows that this compound can act on key enzyme targets such as bacterial DNA gyrase (GYRA), fatty acid synthase (FABI), and dihydrofolate reductase (DHFR), interfering with bacterial DNA replication, lipid synthesis, and nucleic acid metabolism, thereby inhibiting bacterial growth.
Additionally, 2,4-DHAP inhibits enzyme targets such as ERG11 (encoding 14α-demethylase) and CYP51A1 in fungi, demonstrating its antifungal potential. The effect of CDR1 on fungal drug efflux pump suggests it may overcome fungal resistance mechanisms.
Some studies indicate that 2,4-DHAP has antioxidant properties, can scavenge free radicals, reduce oxidative stress damage, and thus protect cells. Its anti-inflammatory activity may be related to inhibiting the release of inflammatory mediators and regulating signaling pathways. Preliminary in vitro experiments have also revealed its potential to inhibit proliferation and induce apoptosis in certain tumor cell lines, but the mechanisms still require further study.
The antibacterial mechanism of 2,4-dihydroxyacetophenone involves multi-target and multi-pathway synergistic effects. Its main targets include:
The multiple actions of these targets give 2,4-DHAP broad-spectrum antimicrobial properties and a low risk of resistance.
According to existing data, 2,4-dihydroxyacetophenone exhibits good druggability parameters:
In terms of pharmacokinetics, although research on metabolism and kinetics in vivo is still insufficient, its physicochemical properties suggest it has good absorption and distribution characteristics in the body. It is expected to be metabolized by the liver and excreted through urine and bile. In the future, systematic ADME (Absorption, Distribution, Metabolism, Excretion) studies and toxicological evaluations are needed to improve its pharmacokinetic characteristics.
2,4-Dihydroxyacetophenone, as a natural multi-target antimicrobial agent, possesses broad-spectrum antibacterial activity and good safety, demonstrating potential as a novel anti-infective drug. Its inhibitory effect on drug-resistant strains is particularly important and is expected to play a key role in combating infections by drug-resistant bacteria. Moreover, its antifungal activity offers new approaches for treating fungal infections.
Future research should focus on:
In addition, the applications of 2,4-DHAP in antioxidant, anti-inflammatory, and potential antitumor fields are also worth further exploration to broaden its medicinal value.
As a natural product with a simple structure but diverse functions, 2,4-dihydroxyacetophenone shows broad prospects for drug development due to its excellent antibacterial activity and good druggability. Systematic pharmacological mechanism research and druggability evaluation have laid a solid foundation for its clinical application. In the future, through multidisciplinary collaboration combined with modern medicinal chemistry, molecular biology, and pharmacokinetic technologies, 2,4-DHAP is expected to become an important new drug in the field of anti-infectivity, meeting the urgent clinical demand for safe and effective antibacterial drugs.
