3,4-Dihydroxyphenylacetaldehyde

Base Information

• Chemical Name: 3,4-Dihydroxyphenylacetaldehyde
• CAS No.: 5707-55-1
• Molecular Formula: C8H8 O3
• Molecular Weight: 152.15
• European Community (EC) Number: 809-292-1
• UNII: F2E9Q24TSL
• DSSTox Substance ID: DTXSID10205680
• Nikkaji Number: J466.586D
• Wikipedia: 3,4-Dihydroxyphenylacetaldehyde
• Wikidata: Q4634065
• Metabolomics Workbench ID: 38395
• Mol file: 5707-55-1.mol

Synonyms:3,4-dihydroxyphenylacetaldehyde;DHPAA aldehyde

Chemical Property of 3,4-Dihydroxyphenylacetaldehyde

Chemical Property:

• Vapor Pressure: 2.11E-05mmHg at 25°C
• Boiling Point: 350.9°Cat760mmHg
• PKA: 9.62±0.10(Predicted)
• Flash Point: 180.2°C
• PSA: 57.53000
• Density: 1.306g/cm³
• LogP: 0.83920
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 135

Purity/Quality:

99.3% ^*data from raw suppliers

Dopal(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC=O)O)O
• Uses: Dopal is the reactive metabolite of dopamine (D533780), an endogenous catecholamine with α and β-adrenergic activity. Dopal is a product of Dopamine (CAT# D533780) catabolism by monoamine oxidase and may be further oxidized to 3,?4-?Dihydroxyphenylacetic Acid (CAT# D454250) via aldehyde dehydrogenase. DOPAL can also be reduced to Hydroxy Tyrosol (CAT# H977000) via cytosolic aldehyde or aldose reductase. DOPAL is harmful to nigrostriatal DA terminals and contributes to the profound putamen DA deficiency found in Parkinson''s disease. Cytosolic and mitochondrial aldehyde dehydrogenase (ALDH) isoenzymes deficiency in mice results in increased levels of DOPAL, causing neurodegeneration and motor dysfunction also associated with Parkinson''s disease.

Technology Process of 3,4-Dihydroxyphenylacetaldehyde

There total 22 articles about 3,4-Dihydroxyphenylacetaldehyde 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: 90.0%

dopamine (51-61-6) → 3,4-Dihydroxyphenylacetaldehyde (5707-55-1)

Guidance literature:

With Halomonas elongata/Co imm pyridoxal phosphate; In toluene; at 37 ℃; for 0.25h; pH=7.5; Flow reactor; Enzymatic reaction;

DOI:10.1002/cbic.201900356

Reference yield: 50.0%

3,4-bis(tetrahydropyran-2-yloxy)phenylacetaldehyde (582289-85-8) → 3,4-Dihydroxyphenylacetaldehyde (5707-55-1)

Guidance literature:

With Amberlite-H⁺; In tetrahydrofuran; water; for 4h;

DOI:10.1016/S0045-2068(03)00019-1

Reference yield: 44.0%

hydroxytyrosol (10597-60-1) → 3,4-Dihydroxyphenylacetaldehyde (5707-55-1)

Guidance literature:

With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at -15 ℃; for 1.5h;

DOI:10.1021/acs.orglett.1c03320

upstream raw materials:

Norepinephrine

Epinephrine

β-3,4-trihydroxyphenethyl-O-α-L-rhamnopyranosyl-(1<*>3)-4-O-caffeoyl-β-D-glucopyranoside

benzo[1,3]dioxol-5-yl-acetaldehyde

Downstream raw materials:

Norlaudanosolin

6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,3,9,10-tetraol

6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,3,10,11-tetraol

hydroxytyrosol

Refernces

• 1、 Tsukamoto, Sachiko,Kato, Haruko,Hirota, Hiroshi,Fusetani, Nobuhiro. "3,4-Dihydroxystyrene Dimers, Inducers of Larval Metamorphosis in Ascidians, from a Marine Sponge Jaspis sp.". . p. 13583 - 13592. Retrieved 1994.
• 2、 Li, Shu Wen,Spaziano, Vincent T.,Burke, William J.. "Synthesis of a biochemically important aldehyde, 3,4- dihydroxyphenylacetaldehyde". . p. 45 - 50. Retrieved 1998.
• 3、 J?rgensen, Steen Ingemann,Tromp, Dorette S.,Van Maarseveen, Jan H.,Vilím, Jan,Wanner, Martin J.,Zuidinga, Ed. "Synthetic Evidence of the Amadori-Type Alkylation of Biogenic Amines by the Neurotoxic Metabolite Dopegal". . . Retrieved 2020/02/04.
• 4、 Wang, Yu,Tappertzhofen, Nadine,Méndez-Sánchez, Daniel,Bawn, Maria,Lyu, Boyu,Ward, John M.,Hailes, Helen C.. "Design and Use of de novo Cascades for the Biosynthesis of New Benzylisoquinoline Alkaloids". supporting information. p. 10120 - 10125. Retrieved 2019/06/27.