Vanillylmandelic acid

Base Information

• Chemical Name: Vanillylmandelic acid
• CAS No.: 55-10-7
• Deprecated CAS: 2394-20-9
• Molecular Formula: C9H10O5
• Molecular Weight: 198.175
• Hs Code.: 29181998
• European Community (EC) Number: 200-224-0
• UNII: 0DQI268449
• DSSTox Substance ID: DTXSID10861583
• Nikkaji Number: J27.583B
• Wikipedia: Vanillylmandelic_acid
• Wikidata: Q901369
• NCI Thesaurus Code: C167084
• Metabolomics Workbench ID: 123038
• ChEMBL ID: CHEMBL1256396
• Mol file: 55-10-7.mol

Synonyms:4 Hydroxy 3 Methoxymandelic Acid;4-Hydroxy-3-Methoxymandelic Acid;Acid, 4-Hydroxy-3-Methoxymandelic;Acid, Methoxyhydroxymandelic;Acid, Vanillylmandelic;Acid, Vanilmandelic;Methoxyhydroxymandelic Acid;Vanillylmandelic Acid;Vanilmandelic Acid

Chemical Property of Vanillylmandelic acid

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 7.5E-08mmHg at 25°C
• Melting Point: 132-134 °C (dec.)(lit.)
• Refractive Index: 1.606
• Boiling Point: 421.3 °C at 760 mmHg
• PKA: 3.42±0.10(Predicted)
• Flash Point: 173.7 °C
• PSA: 86.99000
• Density: 1.44 g/cm³
• LogP: 0.51880
• Storage Temp.: 2-8°C
• Solubility.: H2O: ~50 mg/mL
• Water Solubility.: freely soluble
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 198.05282342
• Heavy Atom Count: 14
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Hydroxy-3-methoxymandelicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C(C(=O)O)O)O
• Uses: A metabolite of catecholamines.

Technology Process of Vanillylmandelic acid

There total 17 articles about Vanillylmandelic 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: 95.7%

2-methoxy-phenol (90-05-1) + Glyoxilic acid (298-12-4) → 4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9)

Guidance literature:

With C₃₈H₅₈Cl₂CrN₃O₂; sodium hydroxide; In water; at 28 ℃; for 1.5h; pH=11; pH-value; Reagent/catalyst; Temperature; Catalytic behavior;

Reference yield: 88.0%

sodium glyoxylate (2706-75-4) + 2-methoxy-phenol (90-05-1) → 4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9)

Guidance literature:

2-methoxy-phenol; With sodium hydroxide; In water; at 10 ℃; under 760.051 Torr; pH=11; Inert atmosphere;

sodium glyoxylate; In water; for 34h; under 760.051 Torr; pH-value; Temperature; Time; Inert atmosphere;

DOI:10.1016/j.tet.2013.07.031

Reference yield: 81.4%

2-methoxy-phenol (90-05-1) + Glyoxilic acid (298-12-4) → 2-hydroxy-3-methoxymandelic acid + 2-hydroxy-3-methoxy-1,5-dimandelic acid (73289-78-8) + 4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9)

Guidance literature:

With sodium hydroxide; succinic acid; In water;

upstream raw materials:

ethyl 4-hydroxy-3-methoxymandelate

2-methoxy-phenol

Glyoxilic acid

chloroform

Downstream raw materials:

2-furanoic acid

ethyl 4-hydroxy-3-methoxymandelate

vanillin

3-methoxy-4-hydroxybenzoic acid

Refernces

• 1、 Mao, Haifang,Wang, Hongzhao,Meng, Tao,Wang, Chaoyang,Hu, Xiaojun,Xiao, Zuobing,Liu, Jibo. "An efficient environmentally friendly CuFe2O4/SiO2catalyst for vanillyl mandelic acid oxidation in water under atmospheric pressure and a mechanism study". . p. 982 - 992. Retrieved 2021/01/25.
• 2、 -. "Method for preparing 3-methoxy-4-hydroxymandelic acid". Paragraph 0081-0145. . Retrieved 2019/07/16.