3,4-Dihydroxymandelic acid

Base Information

• Chemical Name: 3,4-Dihydroxymandelic acid
• CAS No.: 775-01-9
• Molecular Formula: C8H8O5
• Molecular Weight: 184.149
• Hs Code.: 2918290000
• European Community (EC) Number: 212-269-3,238-956-8
• UNII: WDP6VCX5T6
• DSSTox Substance ID: DTXSID30862411
• Nikkaji Number: J128.158E
• Wikipedia: 3,4-Dihydroxymandelic_acid
• Wikidata: Q4634064
• Metabolomics Workbench ID: 37898
• Mol file: 775-01-9.mol

Synonyms:3,4-dihydroxymandelic acid;3,4-dihydroxymandelic acid, (+-)-isomer;3,4-dihydroxymandelic acid, (S)-isomer;3,4-dihydroxymandelic acid, ion(1-);3,4-dihydroxymandelic acid, monosodium salt;DHMA

Chemical Property of 3,4-Dihydroxymandelic acid

Chemical Property:

• Melting Point: 136-137 °C (dec.)
• Boiling Point: 487.5 °C at 760 mmHg
• PKA: 3.42±0.10(Predicted)
• Flash Point: 262.7 °C
• PSA: 97.99000
• Density: 1.644 g/cm³
• LogP: 0.21580
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 184.03717335
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

rac3,4-DihydroxymandelicAcid ^*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

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(C(=O)O)O)O)O
• Uses: A protein kinase C inhibitor.

Technology Process of 3,4-Dihydroxymandelic acid

There total 6 articles about 3,4-Dihydroxymandelic 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: 86.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + Glyoxilic acid (298-12-4) → 3,4-dihydroxymandelic acid (775-01-9)

Guidance literature:

benzene-1,2-diol; With aluminum oxide; sodium hydroxide; In water; for 0.0833333h;

Glyoxilic acid; In water; at 55 ℃; for 24h;

With sulfuric acid; water; at 10 ℃; pH=1.8; Product distribution / selectivity;

Reference yield: 55.4%

1-(4-ethoxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)propane-1,3-diol → 4-ethoxy-2,5-dihydroxy-3-methoxybenzoic acid + 3,4-dihydroxymandelic acid (775-01-9) + 5-methoxybenzene-1,2,4-triol (74202-09-8) + 1-(4-ethoxy-3-methoxyphenyl)propane-1,2,3-triol (77891-26-0)

Guidance literature:

With dihydrogen peroxide; methyltrioxorhenium(VII); acetic acid; In water; at 20 ℃; for 6h; Further byproducts given;

DOI:10.1016/j.bmc.2005.01.049

Reference yield:

→ 3,4-dihydroxymandelic acid (775-01-9)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/jo01095a010 DOI:10.1021/jo01082a622

upstream raw materials:

benzene-1,2-diol

Glyoxilic acid

2-(3,4-carbonyldioxyphenyl)-2-chloroacetic acid

acetone

Downstream raw materials:

(+/-)-2-<3,4-bis(benzyloxy)phenyl>-2-hydroxyethanoic acid

<aminocarbonyl>benzoic acid

(2,2-Dimethyl-benzo[1,3]dioxol-5-yl)-[2-((S)-1-phenyl-ethylcarbamoyl)-benzoylaminooxy]-acetic acid

3,4-methylenedioxyphenylethylamine

Refernces

• 1、 -. "A synthetic preparation method for small carbags hydrochloric acid". Paragraph 0188-0190. . Retrieved 2021/12/08.
• 2、 -. "PROCESS FOR THE PREPARATION OF PHENOLIC COMPOUNDS". Page/Page column 8. . Retrieved 2010/11/25.