614-82-4

Usage

Uses

Used in Pharmaceutical Industry:
2,4-dihydroxyphenylacetic acid is used as a therapeutic agent for the treatment of various neurological and psychiatric disorders. Its role in the brain's reward system and its involvement in mood regulation make it a potential target for the development of medications aimed at treating conditions such as Parkinson's disease, schizophrenia, and addiction.
Used in Research Applications:
Dopamine is utilized as a research tool in neuroscience to study the mechanisms of movement, motivation, and emotional responses. It is also used to investigate the neurobiology of addiction and mood disorders, as well as the role of dopamine in the brain's reward system.
Used in Diagnostic Applications:
2,4-dihydroxyphenylacetic acid is employed as a biomarker in the diagnosis of certain neurological conditions, such as Parkinson's disease, where dopamine levels are often reduced. Measuring dopamine levels can help in the early detection and monitoring of these disorders.
Used in Drug Development:
Dopamine is used as a target for the development of new drugs that aim to modulate its levels or activity in the brain. These drugs may have potential applications in the treatment of neurological and psychiatric disorders associated with dopamine dysregulation.
Used in Neurotransmitter Replacement Therapy:
In conditions where dopamine production is impaired, such as Parkinson's disease, 2,4-dihydroxyphenylacetic acid is used as a replacement therapy to restore normal dopamine levels and alleviate symptoms.
Overall, 2,4-dihydroxyphenylacetic acid, or dopamine, is a multifaceted chemical compound with a wide range of applications in the medical and scientific fields, underscoring its importance in both health and disease.

InChI:InChI=1/C8H8O4/c9-6-2-1-5(3-8(11)12)7(10)4-6/h1-2,4,9-10H,3H2,(H,11,12)

Synthetic route

2-(2,4-bis(benzyloxy)phenyl)acetic acid (66056-40-4) → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	99%

2-(2-bromo-4-hydroxyphenyl)acetic acid (88491-44-5) → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
With copper 8-hydroxyquinolinate; sodium hydroxide	83%
With bis(8-hydroxyquinolato)copper(II); sodium hydroxide at 110℃; for 6h; Concentration; Temperature; Reagent/catalyst;	81%

3-Bromophenol (591-20-8) → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 8 h / 40 °C 2: tin(II) chloride dihdyrate; hydrogenchloride / 3 h / 80 °C 3: bis(8-hydroxyquinolato)copper(II); sodium hydroxide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide 2: tin(II) chloride dihdyrate; hydrogenchloride / water 3: sodium hydroxide; copper 8-hydroxyquinolinate View Scheme

2-(2-bromo-4-hydroxyphenyl)-2-hydroxyacetic acid → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate; hydrogenchloride / water 2: sodium hydroxide; copper 8-hydroxyquinolinate View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → 4-hydroxysalicylic acid (89-86-1)

Conditions	Yield
With iodine; dimethyl sulfoxide at 120℃; for 28h; Sealed tube; Green chemistry;	83%

4-methoxy-benzaldehyde (123-11-5) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(4-methoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	75%

4-hydroxy-benzaldehyde (123-08-0) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(4-hydroxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	75%

3,4-dimethoxy-benzaldehyde (120-14-9) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(3,4-dimethoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	70%

3,4,5-trimethoxy-benzaldehyde (86-81-7) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(3,4,5-trimethoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	68%

3,5-dimethoxybenzaldehdye (7311-34-4) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(3,5-dimethoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	66%

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 7-hydroxy-3-(2’,4’-dihydroxyphenyl)coumarin

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	65%
With sodium acetate; acetic anhydride; acetic acid for 24h; Reflux;	49%

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → (2,4-Dihydroxy-3-iodo-phenyl)-acetic acid + (2,4-Dihydroxy-5-iodo-phenyl)-acetic acid + (2,4-Dihydroxy-3,5-diiodo-phenyl)-acetic acid

Conditions	Yield
With sodium acetate buffer; dihydrogen peroxide; potassium iodide; lactoperoxidase for 0.25h; Ambient temperature; incubation, pH=5.6;

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + dicyclohexyl-carbodiimide (538-75-0) → C16H14O7 + 1,3-Dicyclohexylurea (2387-23-7)

Conditions	Yield
In water; ethyl acetate at 20℃; for 3h;

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → coumestrol (479-13-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride; sodium acetate; acetic acid / 24 h / Reflux 2: copper diacetate / diphenylether / 18 h / 258 °C View Scheme

4-methoxy-benzaldehyde (123-11-5) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-4’-methoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

3,4-dimethoxy-benzaldehyde (120-14-9) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-3’,4’-dimethoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

3,5-dimethoxybenzaldehdye (7311-34-4) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-3’,5’-dimethoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

3,4,5-trimethoxy-benzaldehyde (86-81-7) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-3’,4’,5’-trimethoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

4-hydroxy-benzaldehyde (123-08-0) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 2',4',4-trihydroxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → E-2,2’,4,4’-tetrahydroxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 140 °C / Green chemistry View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → coumestrol (479-13-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / 6 h / 110 °C 2: sodium hydroxide / water 3: copper diacetate; 1,10-Phenanthroline / dimethyl sulfoxide; water / 18 h / 135 °C / Sealed tube; Green chemistry View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → 7-hydroxy-3-(2’,4’-dihydroxyphenyl)coumarin

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 6 h / 110 °C 2: sodium hydroxide / water View Scheme

acetic anhydride (108-24-7) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → C21H16O8

Conditions	Yield
With triethylamine at 110℃; for 6h;

Upstream product

• 591-20-8 3-Bromophenol 
• 88491-44-5 2-(2-bromo-4-hydroxyphenyl)acetic acid 
• 66056-40-4 2-(2,4-bis(benzyloxy)phenyl)acetic acid 

Downstream Products

• 2387-23-7 1,3-Dicyclohexylurea 
• 479-13-0 coumestrol 
• 131391-99-6 3-(2,4-dihydroxyphenyl) coumarin 
• 89-86-1 4-hydroxysalicylic acid 

Relevant academic research and scientific papers

Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

A copper-catalyzed intramolecular cross dehydrogenative C-O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed. This protocol provided a facile and efficient strategy for the construction of natural coumestans and derivatives in moderate to high yields. This transformation exhibited good functional group compatibility and was amenable to substrates with free phenolic hydroxyl groups.

Preparation method of 2,4-dihydroxyphenyl acetic acid

The invention discloses a preparation method of 2,4-dihydroxyphenyl acetic acid, which comprises the following steps: by using m-bromophenol and glyoxalic acid as raw materials, carrying out condensation reaction and acidification to obtain hydroxy o-bromomandelic acid, reducing the hydroxy o-bromomandelic acid to obtain p-hydroxy o-bromophenyl acetic acid, carrying out bromine hydroxylation reaction on the p-hydroxy o-bromophenyl acetic acid in the presence of a catalyst under alkaline conditions, and carrying out acidification to obtain the 2,4-dihydroxyphenyl acetic acid. The method has the advantages of simple and accessible raw materials, simple reaction treatment and higher yield. The obtained intermediate also has important applications.

Syntheses and biological activities of joro spider toxin analogs to spidamine and joramine

In order to study the structure-activity relationships of spidamine and joramine found in the venom of Joro spider, Nephila clavata, we attempted to synthesize various analogs. Six analogs were convergently synthesized according to our previous method for the synthesis of spidamine, N-(3- aminopropyl-β-alanyl)-N'-(2,4-dihydroxyphenylacetyl-L-asparaginyl)-1,5- pentanediamine and joramine, N-(3-aminopropyl-β-alanyl)-N'-(4- hydroxyphenylacetyl-L-asparaginyl)-1,5-pentanediamine. The biological activities of the analogs and four intermediates were compared with those of synthetic spidamine and joramine in three bioassay systems, lobster neuromuscular synapse, cockroaches and mosquito larvae. The glutamate receptors in these systems were inhibited by some analogs, and the D- asparagine- or indoleacetyl-containing analogs were found to be strong inhibitors. These compounds have potential application as insecticides.