2503-44-8

Basic information

• Product Name: 3,4-DIHYDROXYPHENYLACETONE
• Synonyms: 1-(3',4'-DIHYDROXYPHENYL)-2-PROPANONE;1-(3,4-DIHYDROXYPHENYL)-2-PROPANONE;3,4-DIHYDROXYPHENYLACETONE;1-(3,4-Dihydroxyphenyl)-2-propanone 1-(3,4-dihydroxyphenyl)-2-propanone ;1-(3,4-Dihydroxyphenyl)propan-2-one;3,4-dihydroxyphenylacetone AldrichCPR;3,4-dihydroxyphenylacetone 95%
• CAS NO: 2503-44-8
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• Product Categories: Aromatic Ketones (substituted);Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 2503-44-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: -30 °C (decomp)
• Boiling Point: 335.8°Cat760mmHg
• Flash Point: 171.1°C
• Appearance: /
• Density: 1.251g/cm³
• Vapor Pressure: 6.01E-05mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.59±0.10(Predicted)
• CAS DataBase Reference: 3,4-DIHYDROXYPHENYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIHYDROXYPHENYLACETONE(2503-44-8)
• EPA Substance Registry System: 3,4-DIHYDROXYPHENYLACETONE(2503-44-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 2503-44-8(Hazardous Substances Data)

Usage

Description

3,4-Dihydroxyphenylacetic acid, also known as 3',4'-Dihydroxyphenylacetone, is an organic compound that serves as a minor metabolite of 3,4-MDEA, MDMA, and α-methyldopa produced by oxidative deamination. It is an analytical reference standard with chemical properties of a thick yellow oil. This product is primarily intended for forensic and research applications.

Uses

Used in Forensic Applications:
3,4-Dihydroxyphenylacetic acid is used as a forensic analytical standard for the identification and quantification of its parent compounds in biological samples. Its presence helps in the investigation of drug-related crimes and substance abuse cases.
Used in Research Applications:
In research, 3,4-Dihydroxyphenylacetic acid is utilized as a reference compound to study the metabolic pathways and enzyme activities involved in the oxidative deamination of 3,4-MDEA, MDMA, and α-methyldopa. This aids in understanding the pharmacokinetics and pharmacodynamics of these substances.
Used in Metabolite Analysis:
3,4-Dihydroxyphenylacetic acid is used as a metabolite of racemic 3,4-methylenedioxyethylamphetamine and 3,4-methylenedioxyethylamphetamine. This application is crucial for studying the metabolic fate of these compounds in the body and their potential impact on health and drug interactions.

InChI:InChI=1/C9H10O3/c1-6(10)4-7-2-3-8(11)9(12)5-7/h2-3,5,11-12H,4H2,1H3

Synthetic route

guaiacylglycerol-β-guaiacyl ether (7382-59-4) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8)

Conditions	Yield
With methylimidazolium bromide at 110℃; for 0.00277778h; Microwave irradiation; Green chemistry;	95%

guaiacylglycerol-β-guaiacyl ether (7382-59-4) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8) + benzene-1,2-diol (120-80-9)

Conditions	Yield
With methylimidazolium bromide at 110℃; for 0.333333h; Sealed tube; Inert atmosphere; Green chemistry;	A 78% B 21%

1-<3,4-di-(t-butyldimethylsilyloxy)-phenyl>-2-propanone (159423-47-9) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8)

Conditions	Yield
With triethylamine hydrofluoride In tetrahydrofuran for 2h; Ambient temperature;	73%

(+/-)-1-(3,4-dihydroxy-phenyl)-2-dimethylamino-propan-1-one (103565-50-0) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8)

Conditions	Yield
With hydrogenchloride

2-(3,4-dihydroxyphenyl)-1,3-propylenedithioacetal (108378-67-2) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / imidazole / dimethylformamide / Ambient temperature 2: 1.) n-BuLi, i-Pr2NH / 1.) THF, -76 deg C, 0.5 h, 2.) THF, -76 deg C, 1 h 3: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 4: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

2-<3,4-di-(t-butyldimethylsilyloxy)-phenyl>-1,3-propylenedithioacetal (159423-45-7) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) n-BuLi, i-Pr2NH / 1.) THF, -76 deg C, 0.5 h, 2.) THF, -76 deg C, 1 h 2: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 3: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1-<3,4-di-(t-butyldimethylsilyloxy)-phenyl>-1-oxo-propanone-1,3-propylenedithioacetal (159423-46-8) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 2: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

3,4-dihydroxybenzaldehyde (139-85-5) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 88 percent / AcOH, BF3*Et2O / 5 °C 2: 95 percent / imidazole / dimethylformamide / Ambient temperature 3: 1.) n-BuLi, i-Pr2NH / 1.) THF, -76 deg C, 0.5 h, 2.) THF, -76 deg C, 1 h 4: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 5: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

S(-)-carbidopa (302-53-4, 14585-65-0, 28860-95-9, 28875-92-5) → 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8) + 6,7-dihydroxy-3-methylcinnoline (1176784-51-2) + 3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid (53832-94-3)

Conditions	Yield
With bovine myeloperoxidase; dihydrogen peroxide In aq. buffer at 20℃; pH=6; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;

1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8) → 4-(1,3-dimethyl-2-naphthyl)-1,2-benzenediol

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 1h; condensation;	77%

diazomethane (186581-53-3, 908094-01-9) + 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With diethyl ether

Upstream product

• 103565-50-0 (+/-)-1-(3,4-dihydroxy-phenyl)-2-dimethylamino-propan-1-one 
• 159423-47-9 1-<3,4-di-(t-butyldimethylsilyloxy)-phenyl>-2-propanone 
• 108378-67-2 2-(3,4-dihydroxyphenyl)-1,3-propylenedithioacetal 
• 159423-45-7 2-<3,4-di-(t-butyldimethylsilyloxy)-phenyl>-1,3-propylenedithioacetal 
• 159423-46-8 1-<3,4-di-(t-butyldimethylsilyloxy)-phenyl>-1-oxo-propanone-1,3-propylenedithioacetal 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 302-53-4 S(-)-carbidopa 

Downstream Products

• 776-99-8 3,4-dimethoxyphenylacetone 

Relevant articles and documents

Imidazolium-Based Ionic Liquids as Efficient Reagents for the C?O Bond Cleavage of Lignin

The demethylation of lignin in ionic liquids (ILs) was investigated by using pure lignin model monomers and dimers together with dioxane-isolated lignins from poplar, miscanthus, and maize. Different methylimidazolium ILs were compared and the samples were treated with two different heating processes: microwave irradiation and conventional heating in a sealed tube. The conversion yield and influence of the treatment on the lignin structure were assessed by 31P NMR spectroscopy, size-exclusion chromatography, and thioacidolysis. The acidic methylimidazolium IL [HMIM]Br was shown to be an effective combination of solvent and reagent for the demethylation and depolymerization of lignin. The relatively mild reaction conditions, the clean work-up, and the ability to reuse the IL makes the described procedure an attractive and new green method for the conversion of lignin to produce phenol-rich lignin oligomers.

The synthesis of 1-(3,4-dihydroxyphenyl)-2-propanone and 1-(3,4-dihydroxyphenyl)-2-propanol

Acetylation of 1,3-propylenedithioacetal of 3,4-dihydroxybenzaldehyde silyl ether 5 followed by reductive desulfurization of the masking group gave ketone 7 which was reduced to alcohol 8. Hydrolysis of the silyl protecting groups in 7 and 8 afforded the title compounds which were metabolites of 1-(4-hydroxy-3-methoxyphenyl)-2-propanone, found in smoked meat.