3,4-Dihydroxymandelaldehyde

Base Information

• Chemical Name: 3,4-Dihydroxymandelaldehyde
• CAS No.: 13023-73-9
• Molecular Formula: C8H8 O4
• Molecular Weight: 168.149
• Hs Code.: 2912499000
• DSSTox Substance ID: DTXSID30897223
• Nikkaji Number: J678.576J
• Wikidata: Q27103374
• Metabolomics Workbench ID: 38838
• Mol file: 13023-73-9.mol

Synonyms:3,4-dihydroxyphenylglycolaldehyde

Chemical Property of 3,4-Dihydroxymandelaldehyde

Chemical Property:

• Vapor Pressure: 7.64E-07mmHg at 25°C
• Boiling Point: 391.9°Cat760mmHg
• PKA: 9.43±0.10(Predicted)
• Flash Point: 205°C
• PSA: 77.76000
• Density: 1.466g/cm³
• LogP: 0.33010
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dihydroxyphenylglycolaldehyde(Dopegal) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(C=O)O)O)O
• Uses: 3,4-Dihydroxyphenylglycolaldehyde (Dopegal) is the monoamine oxidase metabolite of dopamine which is toxic of in a concentrated amount and may be a target for Alzheimer or Parkinson’s therapy.

Technology Process of 3,4-Dihydroxymandelaldehyde

There total 10 articles about 3,4-Dihydroxymandelaldehyde 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: 92.0%

4-(1-hydroxy-2,2-dimethoxyethyl)benzene-1,2-diol → 2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde (13023-73-9) + C16H16O8

Guidance literature:

With trifluoroacetic acid; In water; at 45 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.9b01948

Reference yield: 60.0%

2-(3,4-dihydroxy-α-hydroxybenzyl)-1,3-dithiane → 2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde (13023-73-9)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In water; acetonitrile; for 3h; Heating;

DOI:10.1006/bioo.1994.1027

Reference yield: 50.0%

2-(3,4-bis(tetrahydropyran-2-yloxy)phenyl)-2-(tetrahydropyran-2-yloxy)acetaldehyde (582289-88-1) → 2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde (13023-73-9)

Guidance literature:

2-(3,4-bis(tetrahydropyran-2-yloxy)phenyl)-2-(tetrahydropyran-2-yloxy)acetaldehyde; With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 4h;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 3h;

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

upstream raw materials:

2-(3,4-bis(tetrahydropyran-2-yloxy)phenyl)-2-(tetrahydropyran-2-yloxy)acetaldehyde

3,4-dihydroxyphenylacetate

2-(3,4-dihydroxyphenyl)acetic acid methyl ester

3,4-bis(tetrahydropyran-2-yloxy)phenylacetic acid methyl ester

Refernces

• 1、 Duncan. "The preparation of some biochemically important aldehydes". . p. 920 - 922. Retrieved 1975.
• 2、 Narayanan, Jayan,Hayakawa, Yoshio,Fan, Junfa,Kirk, Kenneth L.. "Convenient syntheses of biogenic aldehydes, 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde". . p. 191 - 197. Retrieved 2007/10/03.