4-Hydroxyphenylglycolic acid

Base Information

• Chemical Name: 4-Hydroxyphenylglycolic acid
• CAS No.: 1198-84-1
• Deprecated CAS: 7198-10-9
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 2918290000
• European Community (EC) Number: 214-839-7,230-569-2
• UNII: HV52GS53BA
• DSSTox Substance ID: DTXSID70862596
• Nikkaji Number: J100.348H
• Wikipedia: 4-Hydroxymandelic_acid
• Wikidata: Q10395570
• Metabolomics Workbench ID: 78506
• ChEMBL ID: CHEMBL2087618
• Mol file: 1198-84-1.mol

Synonyms:4-hydroxymandelic acid;4-hydroxymandelic acid, (D)-isomer;para-hydroxymandelic acid;pisolithin B

Chemical Property of 4-Hydroxyphenylglycolic acid

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 2.67E-07mmHg at 25°C
• Melting Point: 82-85 °C(lit.)
• Boiling Point: 405.4 °C at 760 mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: 213.1 °C
• PSA: 77.76000
• Density: 1.48 g/cm³
• LogP: 0.51020
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

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

4-HydroxymandelicAcid ^*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(=CC=C1C(C(=O)O)O)O
• Uses: 4-Hydroxymandelic Acid is a useful synthetic intermediate in the synthesis of Hydroxyatenolol (H802480); a metabolite of Atenolol (A790075) which is a cardioselective β-adrenergic blocker, antihypertensive, antianginal, and antiarrhythmic (class II).

Technology Process of 4-Hydroxyphenylglycolic acid

There total 22 articles about 4-Hydroxyphenylglycolic 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: 94.6%

Glyoxilic acid (298-12-4) + phenol (108-95-2,27073-41-2) → 4-hydroxymandelic acid (1198-84-1)

Guidance literature:

With sodium hydroxide; at 25 ℃; for 22h; pH=12; pH-value; Temperature; Reagent/catalyst;

Reference yield: 78.0%

chloroform (67-66-3,8013-54-5) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 4-hydroxymandelic acid (1198-84-1)

Guidance literature:

With 1-butyl-3-methylimidazolium hexafluorophosphate β-cyclodextrin inclusion complex; sodium hydroxide; In water; at 50 ℃; for 6.5h;

DOI:10.3184/174751911X13131678182481

Reference yield: 76.9%

Glyoxilic acid (298-12-4) + phenol (108-95-2,27073-41-2) → 4-hydroxymandelic acid (1198-84-1) + 2-hydroxymandelic acid (1678-71-3)

Guidance literature:

With zinc(II) oxide; In water; at 70 ℃; for 3h;

upstream raw materials:

pisolithin A

methyl 2-(4-hydroxyphenyl)-2-hydroxyacetate

p-hydroxymandelic acid ethyl ester

4-hydroxy-benzaldehyde

Downstream raw materials:

4-hydroxy-3,5-diiodo-mandelic acid

(+)-p-hydroxy-O-acetylmandelic acid

(-)-p-hydroxymandelic acid

2-{(S)-4-[2-Hydroxy-2-(4-hydroxy-phenyl)-acetylamino]-3-oxo-isoxazolidin-2-yl}-5-oxo-tetrahydro-furan-2-carboxylic acid benzhydryl ester

Refernces

• 1、 Ohashi,Takahashi,Nagamachi,et al.. "A new method for 5-(4-hydroxyphenyl)hydantoin synthesis". . p. 831 - 838. Retrieved 1981.
• 2、 -. "Preparation method of P-hydroxybenzaldehyde". Paragraph 0051-0065; 0068-0070; 0072-0074; 0076-0077; .... . Retrieved 2021/07/17.
• 3、 Varala, Ravi,Kotra, Vijay,Alam, M. Mujahid,Kumar, N. Ramesh,Ganapaty,Adapa, Srinivas R.. "Synthesis of mandelic acid derived phthalimides as a new class of antiinflammatory and antimicrobial agents". . p. 1243 - 1248. Retrieved 2008/12/23.