3,4-Dihydroxyphenylacetic acid

Base Information

• Chemical Name: 3,4-Dihydroxyphenylacetic acid
• CAS No.: 102-32-9
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 29182900
• European Community (EC) Number: 203-024-1
• NSC Number: 73191
• UNII: KEX5N0R4N5
• DSSTox Substance ID: DTXSID9074430
• Nikkaji Number: J804D
• Wikipedia: 3,4-Dihydroxyphenylacetic_acid
• Wikidata: Q4634071
• Metabolomics Workbench ID: 37733
• ChEMBL ID: CHEMBL1284
• Mol file: 102-32-9.mol

Synonyms:3,4 Dihydroxyphenylacetic Acid;3,4-Dihydroxyphenylacetic Acid;3,4-Dihydroxyphenylacetic Acid, Monosodium Salt;DOPAC;Homoprotocatechuic Acid

Chemical Property of 3,4-Dihydroxyphenylacetic acid

Chemical Property:

• Appearance/Colour: beige to light brown crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 127-130 °C(lit.)
• Refractive Index: 1.628
• Boiling Point: 418.4 °C at 760 mmHg
• PKA: 4.42±0.10(Predicted)
• Flash Point: 221 °C
• PSA: 77.76000
• Density: 1.478 g/cm³
• LogP: 0.72490
• Storage Temp.: −20°C
• Solubility.: water: soluble50mg/mL, clear, almost colorless
• Water Solubility.: Soluble in water and methanol.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dihydroxyphenylacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC(=C(C=C1CC(=O)O)O)O
• Description: 3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine. Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline).DOPAC can be oxidized by hydrogen peroxide, leading to the formation of toxic metabolites which destroy dopamine storage vesicles in the substantia nigra. This may contribute to the failure of levodopa treatment of Parkinson's disease. A MAO-B inhibitor such as selegiline or rasagiline can prevent this from happening.wikipedia
• Uses: 3,4-Dihydroxyphenylacetic Acid is a metabolite of Dopamine (D533782). 3,4-Dihydroxyphenylacetic acid is an important metabolite when studying the behavior of the dopaminergic system.

Technology Process of 3,4-Dihydroxyphenylacetic acid

There total 35 articles about 3,4-Dihydroxyphenylacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.7%

4-hydroxyphenylacetate (156-38-7) → 3,4-dihydroxyphenylacetate (102-32-9)

Guidance literature:

With ascorbic acid; In aq. phosphate buffer; at 25 ℃;

DOI:10.1016/j.procbio.2018.03.028

Reference yield: 96.9%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) → 3,4-dihydroxyphenylacetate (102-32-9)

Guidance literature:

With hydrogenchloride; acetic acid; In water; at 80 ℃; for 6h;

Reference yield: 78.0%

3,4-dihydroxymandelic acid → 3,4-dihydroxyphenylacetate (102-32-9)

Guidance literature:

With formic acid; phosphoric acid; sodium hydrogensulfite; In water; at 100 ℃; for 9h; under 3750.3 Torr;

upstream raw materials:

(3,4-Dimethoxyphenyl)acetic acid

2-(3,4-dimethoxyphenyl)-2-hydroxyacetonitrile

1,3-benzodioxole-5-acetic acid

(3,4-dihydroxy-phenyl)-acetonitrile

Downstream raw materials:

(3,4-Dimethoxyphenyl)acetic acid

8-(3,4-dihydroxy-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione

3,4-dihydroxyphenylacetic acid diacetate

<3,4-bis(benzyloxy)phenyl>acetic acid

Refernces

• 1、 Nonoyama, Nobuaki,Chiba, Kazuhiko,Hisatome, Kaori,Suzuki, Hitomi,Shintani, Futoshi. "Nitration and hydroxylation of substituted phenols by peroxynitrite. Kinetic feature and an alternative mechanistic view". . p. 6933 - 6937. Retrieved 1999.
• 2、 Guazzaroni, Melissa,Crestini, Claudia,Saladino, Raffaele. "Layer-by-Layer coated tyrosinase: An efficient and selective synthesis of catechols". . p. 157 - 166. Retrieved 2012.
• 3、 Snape,Pileblad,Ekman,Magnusson,Carlsson,Engel. "The effects of 1-methyl-4-phenylpyridinium ion (MPP+) on the efflux and metabolism of endogenous dopamine in rat striatal slices". . p. 620 - 626. Retrieved 1988.
• 4、 Gallardo, Elena,Madrona, Andrs,Palma-Valds, Roco,Trujillo, Mariana,Espartero, Jos Luis,Santiago, Marti. "The effect of hydroxytyrosol and its nitroderivatives on catechol-O-methyl transferase activity in rat striatal tissue". . p. 61086 - 61091. Retrieved 2014.
• 5、 Dhammaraj, Taweesak,Phintha, Aisaraphon,Pinthong, Chatchadaporn,Medhanavyn, Dheeradhach,Tinikul, Ruchanok,Chenprakhon, Pirom,Sucharitakul, Jeerus,Vardhanabhuti, Nontima,Jiarpinitnun, Chutima,Chaiyen, Pimchai. "p-Hydroxyphenylacetate 3-Hydroxylase as a Biocatalyst for the Synthesis of Trihydroxyphenolic Acids". . p. 4492 - 4502. Retrieved 2015.
• 6、 Willeke, U.,Weltring, K. M.,Barz, W.,VanEtten, H. D.. "DEGRADATION OF THE ISOFLAVONE BIOCHANIN A BY ISOLATES OF NECTRIA HAEMATOCOCCA (FUSARIUM SOLANI)". . p. 1539 - 1542. Retrieved 1983.
• 7、 Moore, Thea J.,Joseph, Melissa J.,Allen, Barry W.,Coury Jr., Louis A.. "Enzymatically amplified voltammetric sensor for microliter sample volumes of salicylate". . p. 1896 - 1902. Retrieved 1995.
• 8、 -. "Preparation method of hydroxytyrosol". Paragraph 0057; 0059. . Retrieved 2019/10/01.
• 9、 Hu, Yuheng,Wang, Bing,Yang, Jie,Liu, Teng,Sun, Jie,Wang, Xiaojing. "Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents". . p. 15 - 30. Retrieved 2018/10/31.