528-21-2

Basic information

• Product Name: 2',3',4'-TRIHYDROXYACETOPHENONE
• Synonyms: EUGALLOL;GALLACETOPHENONE;2',3',4'-TRIHYDROXYACETOPHENONE;2,3,4-TRIHYDROXYACETOPHENONE;PYROGALLOL MONOACETATE;1-(2,3,4-trihydroxyphenyl)-ethanon;1-(2,3,4-Trihydroxyphenyl)ethanone;2’,3’,4’-trihydroxy-acetophenon
• CAS NO: 528-21-2
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• EINECS: 208-430-2
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Building block
• Mol File: 528-21-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 169-172 °C(lit.)
• Boiling Point: 257.07°C (rough estimate)
• Flash Point: 208.7 °C
• Appearance: yellow-green crystalline powder
• Density: 1.3037 (rough estimate)
• Refractive Index: 1.5090 (estimate)
• PKA: 7.81±0.23(Predicted)
• Merck: 14,4342
• CAS DataBase Reference: 2',3',4'-TRIHYDROXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',4'-TRIHYDROXYACETOPHENONE(528-21-2)
• EPA Substance Registry System: 2',3',4'-TRIHYDROXYACETOPHENONE(528-21-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: AN0527000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 528-21-2(Hazardous Substances Data)

Usage

Description

2',3',4'-Trihydroxyacetophenone is an organic compound characterized by the presence of three hydroxyl groups at the 2', 3', and 4' positions of the acetophenone molecule. It is a versatile chemical intermediate with a wide range of applications in various industries due to its unique structural properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2',3',4'-Trihydroxyacetophenone is used as an intermediate in the synthesis of various pharmaceutical compounds, including chromenone and quinolinone derivatives. These derivatives exhibit potent antioxidant properties, which can be beneficial in the development of drugs targeting oxidative stress-related diseases and conditions.
Used in Chemical Synthesis:
2',3',4'-Trihydroxyacetophenone is used as a reagent in the synthesis of chromenone and quinolinone derivatives, which are known for their antioxidant properties. These compounds can be further utilized in the development of new drugs and pharmaceuticals with potential applications in various therapeutic areas.
Used in Antioxidant Applications:
Due to its antioxidant properties, 2',3',4'-Trihydroxyacetophenone can be used in the development of antioxidant formulations for various industries, such as the food and cosmetics industries. Antioxidants are essential in preventing the oxidation of fats and oils, as well as in protecting the skin from oxidative stress caused by environmental factors.
Used in Antiseptic Applications:
2',3',4'-Trihydroxyacetophenone is also used as an antiseptic, which can be beneficial in the development of disinfectants and sanitizers for medical and personal care applications. Its antimicrobial properties can help in reducing the risk of infections and promoting overall hygiene.

Preparation

Preparation by Fries rearrangement of pyrogallol triacetate with aluminium chloride without solvent.

Upstream product

• 525-52-0 pyrogallol triacetate 
• 3424-77-9 3-formyl-2,4-dihydroxyacetophenone 
• 108-24-7 acetic anhydride 
• 87-66-1 2-hydroxyresorcinol 
• 64-19-7 acetic acid 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 75-36-5 acetyl chloride 
• 197571-05-4 4-cyano-1,3-phenylene diacetate 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 5715-02-6 2-acetoxybenzonitrile 
• 17345-68-5 ω-chloro-2,3,4-trihydroxyacetophenone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 5396-18-9 2'-hydroxy-3',4'-dimethoxyacetophenone 

Downstream Products

• 94101-89-0 1-(5-tert-butyl-2,3,4-trihydroxy-phenyl)-ethanone 
• 16555-68-3 4-ethyl-pyrogallol 
• 294639-07-9 4.2'.3'.4'-tetrahydroxy-trans-chalcone 
• 53219-85-5 2',3',4'-trihydroxy-3,4-dimethoxy-trans-chalcone 
• 484-76-4 okanin 
• 5396-18-9 2'-hydroxy-3',4'-dimethoxyacetophenone 
• 69114-99-4 4-benzyloxy-2,3-dihydroxyacetophenone 
• 2652-27-9 1-(3,4-bis(benzyloxy)-2-hydroxyphenyl)ethanone 
• 131944-43-9 1-Phenyl-3-(2,3,4-trihydroxy-phenyl)-propane-1,3-dione 
• 53219-86-6 (E)-3-(3-Benzyloxy-phenyl)-1-(2,3,4-trihydroxy-phenyl)-propenone 
• 53219-83-3 (Z)-3-(4-Chloro-phenyl)-1-(2,3,4-trihydroxy-phenyl)-propenone 
• 53219-85-5 (E)-3-(3,4-Dimethoxy-phenyl)-1-(2,3,4-trihydroxy-phenyl)-propenone 
• 53219-87-7 (2E,4Z)-5-Phenyl-1-(2,3,4-trihydroxy-phenyl)-penta-2,4-dien-1-one 
• 72712-20-0 2,3,4-triacetoxyacetophenone 

Relevant articles and documents

Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones

American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.

Preparation method of 7,8-dihydroxy flavone

The invention relates to a preparation method of 7,8-dihydroxy flavone, and belongs to the technical field of synthesis of medical intermediates. The preparation method comprises the following steps:by taking pyrogallol as a raw material, introducing an acetyl group to synthesize DHF1; protecting three phenolic hydroxyl groups to synthesize DHF2; selectively reducing the ortho-hydroxyl group of the acetyl group to synthesize DHF3; carrying out an aldol condensation reaction on DHF3 and benzaldehyde to prepare DHF4; carrying out a cyclization reaction under the condition of iodine catalysis toobtain DHF5; and finally carrying out a hydrolysis reaction to generate the final product. The method is simple and convenient to operate, reasonable in reaction process, low in production cost, goodin product quality, free of environmental pollution and suitable for industrial production, wherein the content of the product is higher than 98%.

Synthesis of structurally diverse biflavonoids

Synthetic biflavonoids are associated with interesting biological activities, yet they remain poorly explored within drug discovery. Recent years have witnessed a growing interest in synthetic approaches that can provide access to structurally novel biflavonoids so that the biological usefulness of this compound class can be more fully investigated. Herein, we report upon the exploration of strategies based around Suzuki-Miyaura cross-coupling and alcohol methylenation for the synthesis of two classes of biflavonoids: (i) rare ‘hybrid’ derivatives containing flavonoid monomers belonging to different subclasses, and (ii) homodimeric compounds in which the two flavonoid monomers are linked by a methylenedioxy group. Application of these strategies enabled the preparation of a structurally diverse collection of novel biflavonoids from readily-available starting materials, thereby facilitating the probing of uncharted regions of biologically interesting chemical space.