5707-55-1

Basic information

• Product Name: 2-(3,4-dihydroxyphenyl)acetaldehyde
• Synonyms: 2-(3,4-dihydroxyphenyl)acetaldehyde;3,4-Dihydroxyphenylacetaldehyde;Dopal (>80%)
• CAS NO: 5707-55-1
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• Product Categories: Aromatics, Neurochemicals, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 5707-55-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 350.9°Cat760mmHg
• Flash Point: 180.2°C
• Appearance: /
• Density: 1.306g/cm³
• Vapor Pressure: 2.11E-05mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.62±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-(3,4-dihydroxyphenyl)acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dihydroxyphenyl)acetaldehyde(5707-55-1)
• EPA Substance Registry System: 2-(3,4-dihydroxyphenyl)acetaldehyde(5707-55-1)

Safety Data

• Hazardous Substances Data: 5707-55-1(Hazardous Substances Data)

Usage

Description

2-(3,4-dihydroxyphenyl)acetaldehyde is a phenylacetaldehyde derivative with hydroxy groups substituted at the 3 and 4 positions of the phenyl group. It is a reactive metabolite of dopamine, an endogenous catecholamine with α and β-adrenergic activity.

Uses

Used in Pharmaceutical Industry:
2-(3,4-dihydroxyphenyl)acetaldehyde is used as an intermediate compound in the synthesis of various pharmaceuticals, particularly those targeting neurodegenerative diseases such as Parkinson's disease. Its role in the catabolism of dopamine and its potential harmful effects on nigrostriatal dopamine terminals make it a significant molecule for understanding the underlying mechanisms of neurodegeneration and motor dysfunction associated with Parkinson's disease.
Used in Chemical Research:
2-(3,4-dihydroxyphenyl)acetaldehyde serves as a valuable compound in chemical research, particularly in the study of the reactivity and properties of phenylacetaldehyde derivatives with hydroxy substitutions. This knowledge can be applied to the development of new synthetic routes and the design of novel molecules with potential applications in various fields, including pharmaceuticals, materials science, and environmental chemistry.
Used in Analytical Chemistry:
As a specific metabolite of dopamine, 2-(3,4-dihydroxyphenyl)acetaldehyde can be used as a biomarker in analytical chemistry for the detection and monitoring of dopamine levels in biological samples. This can be particularly useful in the diagnosis and treatment of conditions related to dopamine dysregulation, such as Parkinson's disease and other neurodegenerative disorders.
Used in Environmental Science:
The study of 2-(3,4-dihydroxyphenyl)acetaldehyde can also contribute to the understanding of the environmental fate and impact of dopamine and its metabolites. This knowledge can be applied to the development of strategies for the remediation of polluted environments and the assessment of the ecological risks associated with the release of these compounds into the environment.

InChI:InChI=1/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2

Upstream product

• 61854-89-5 3,4-di-[(tetrahydro-2H-pyran-2-yl)oxy]-benzaldehyde 
• 51-67-2 tyrosamine 
• 60-18-4 L-tyrosine 
• 10597-60-1 hydroxytyrosol 
• 1126-61-0 4-allylpyrocatechol 
• 582289-84-7 3,4-bis(tetrahydropyran-2-yloxy)phenylacetic acid methyl ester 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 582289-85-8 3,4-bis(tetrahydropyran-2-yloxy)phenylacetaldehyde 
• 59-92-7 levodopa 
• 86119-84-8 phosphoric acid 
• 51-43-4 L-epinephrine 
• 6543-34-6 benzo[1,3]dioxol-5-yl-acetaldehyde 
• 90985-63-0 β-3,4-trihydroxyphenethyl-O-α-L-rhamnopyranosyl-(1<*>3)-4-O-caffeoyl-β-D-glucopyranoside 
• 329-65-7 Epinephrine 

Downstream Products

• 4747-99-3 Norlaudanosolin 
• 10597-60-1 hydroxytyrosol 
• 100621-42-9 (3,4-dihydroxy-phenyl)-acetaldehyde-(2,4-dinitro-phenylhydrazone) 
• 109047-32-7 (3,4-dihydroxy-phenyl)-acetaldehyde-semicarbazone 
• 53905-57-0 6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,3,9,10-tetraol 
• 53905-56-9 6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,3,10,11-tetraol 

Relevant articles and documents

Assessment of the in vitro and in vivo toxicity of 3,4- dihydroxyphenylacetaldehyde (DOPAL)

This work was carried out in order to evaluate the in vitro and in vivo toxicity of 3,4-dihydroxyphenylacetaldehyde (DOPAL). This aldehyde is formed from dopamine (DA) by monoamine oxidases (MAO) and is mainly oxidised to 3,4-dihydroxyphenylacetic acid by

The rearrangement of epinephrine.

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Transaminase-Mediated Amine Borrowing via Shuttle Biocatalysis

Shuttle catalysis has emerged as a useful methodology for the reversible transfer of small functional groups, such as CO and HCN, and goes far beyond transfer hydrogenation chemistry. While a biocatalytic hydrogen-borrowing methodology is well established, the biocatalytic borrowing of alternative functional groups has not yet been realized. Herein, we present a new concept of amine borrowing via biocatalytic shuttle catalysis, which has no counterpart in chemo-shuttle catalysis and allows efficient intermolecular amine shuttling to generate reactive intermediates in situ. By coupling this dynamic exchange with an irreversible downstream step to displace the reaction equilibrium in the forward direction, high conversion to target products can be achieved. We showcase the potential of this amine-borrowing methodology using a biocatalytic equivalent of both the Knorr-pyrrole synthesis and Pictet-Spengler reaction.

Design and Use of de novo Cascades for the Biosynthesis of New Benzylisoquinoline Alkaloids

The benzylisoquinoline alkaloids (BIAs) are an important group of secondary metabolites from higher plants and have been reported to show significant biological activities. The production of BIAs through synthetic biology approaches provides a higher-yielding strategy than traditional synthetic methods or isolation from plant material. However, the reconstruction of BIA pathways in microorganisms by combining heterologous enzymes can also give access to BIAs through cascade reactions. Most importantly, non-natural BIAs can be generated through such artificial pathways. In the current study, we describe the use of tyrosinases and decarboxylases and combine these with a transaminase enzyme and norcoclaurine synthase for the efficient synthesis of several BIAs, including six non-natural alkaloids, in cascades from l-tyrosine and analogues.

One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine

We describe novel chemoenzymatic routes to (S)-benzylisoquinoline and (S)-tetrahydroprotoberberine alkaloids using the enzymes transaminase (TAm) and norcoclaurine synthase (NCS) in a one-pot, one-substrate 'triangular' cascade. Employment of up to two C-