4-Hydroxyphenylacetic acid

Base Information

• Chemical Name: 4-Hydroxyphenylacetic acid
• CAS No.: 156-38-7
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 29182990
• European Community (EC) Number: 205-851-3
• NSC Number: 27460,25066
• UNII: 3J9SHG0RCN
• DSSTox Substance ID: DTXSID5059745
• Nikkaji Number: J5.873D
• Wikipedia: 4-hydroxyphenylacetic acid
• Wikidata: Q4637160
• Metabolomics Workbench ID: 37028
• ChEMBL ID: CHEMBL1772
• Mol file: 156-38-7.mol

Synonyms:4-hydroxyphenylacetic acid;p-hydroxyphenylacetic acid;para-hydroxyphenylacetic acid

Chemical Property of 4-Hydroxyphenylacetic acid

Chemical Property:

• Appearance/Colour: white or light yellow crystalline powder
• Vapor Pressure: 2.15E-05mmHg at 25°C
• Melting Point: 148-151 °C(lit.)
• Refractive Index: 1.4945 (estimate)
• Boiling Point: 346.6 °C at 760 mmHg
• PKA: 4.50±0.10(Predicted)
• Flash Point: 177.6 °C
• PSA: 57.53000
• Density: 1.319 g/cm³
• LogP: 1.01930
• Storage Temp.: Store below +30°C.
• Solubility.: 50g/l
• Water Solubility.: Soluble in dimethyl sulfoxide and methanol. Slightly soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxyphenylacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC(=CC=C1CC(=O)O)O
• Description: 4-Hydroxyphenylacetic acid is an acetate derivative used in the acylation of phenols and amines1. It is an active component of Chinese herb Aster tataricus which had been widely used in China for the treatment of pulmonary diseases, HBV, and carcinoma. It is an active metabolite of amino acid metabolism. Study has also shown that it can attenuate inflammation and edema through suppressing hypertonic and hypoxic induction of HIF-1α in seawater aspiration-induced lung injury in rats. In chemical industry, it is an intermediate used to synthesize atenolol and 3, 4-dihydroxyphenylacetic acid.
• Uses: A compound present in olive oil. An important fine chemical intermediate with broad prospects for application development. It is used as a reagent in the acylation of phenols and amines. It is also used for fluorometric determination of oxidative enzymes.

Technology Process of 4-Hydroxyphenylacetic acid

There total 179 articles about 4-Hydroxyphenylacetic 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: 97.3%

p-Coumaric Acid (7400-08-0,50940-26-6) → 4-hydroxyphenylacetate (156-38-7) + p-hydroxyphenethyl alcohol (501-94-0)

Guidance literature:

With β-D-glucose; oxygen; for 18h; Reagent/catalyst; Enzymatic reaction;

DOI:10.1039/d0gc03595e

Reference yield:

4-hydroxyphenylpiruvic acid (156-39-8) → 4-hydroxyphenylacetate (156-38-7) + (4-oxo-2,5-cyclohexadien-1-yl)acetic acid (55604-87-0) + homogentisic acid (451-13-8) + (S)-α,4-dihydroxy-benzeneacetic acid (13244-75-2)

Guidance literature:

With oxygen; iron(II) sulfate; In aq. phosphate buffer; at 25 ℃; pH=7; Enzymatic reaction;

DOI:10.1021/bi400534q

Reference yield:

4-hydroxyphenylpiruvic acid (156-39-8) → 4-hydroxyphenylacetate (156-38-7) + (4-oxo-2,5-cyclohexadien-1-yl)acetic acid (55604-87-0) + homogentisic acid (451-13-8)

Guidance literature:

With oxygen; iron(II) sulfate; In aq. phosphate buffer; at 25 ℃; pH=7; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1021/bi400534q

upstream raw materials:

4-Methoxyphenylacetic acid

4-methoxymandelonitrile

4-cyanomethylphenol

(4-sulfo-phenyl)-acetic acid

Downstream raw materials:

Methyl 4-hydroxyphenylacetate

4-butoxyphenylacetic acid

methyl 2-(4-(2-bromoethoxy)phenyl)acetate

1,2-bis-(4-methoxycarbonylmethyl-phenoxy)-ethane

Refernces

• 1、 Ott,Mattano,Coleman. "-". . p. 2633. Retrieved 1946.
• 2、 Givens, Richard S.,Heger, Dominik,Hellrung, Bruno,Kamdzhilov, Yavor,Mac, Marek,Conrad II, Peter G.,Cope, Elizabeth,Lee, Jong I.,Mata-Segreda, Julio F.,Schowen, Richard L.,Wirz, Jakob. "The photo-favorskii reaction of p-hydroxyphenacyl compounds is initiated by water-assisted, adiabatic extrusion of a triplet biradical". . p. 3307 - 3309. Retrieved 2008.
• 3、 Torti, Edoardo,Havel, Václav,Yawer, Mirza A.,Ludvíková, Lucie,Babiak, Michal,Klán, Petr,Sindelar, Vladimir. "Supramolecular Storage and Controlled Photorelease of an Oxidizing Agent using a Bambusuril Macrocycle". . p. 16768 - 16772. Retrieved 2017.
• 4、 Holzer,Zinke. "-". . p. 901,908. Retrieved 1953.
• 5、 Kumar, Ashok,Rane, Ramkrishna A.,Ravindran, Vaikyparambil K.,Dike, Suneel Y.. "Facile 1,2-aryl migration of 2-halomethyl-2-(4'-hydroxyphenyl) ketals: A novel single step synthesis of 4-hydroxyphenylacetic acid and its derivatives". . p. 1133 - 1141. Retrieved 1997.
• 6、 Asada,Miyase,Fukushima. "Sesquiterpene lactones from Ixeris tamagawaensis KITAM. III". . p. 3403 - 3409. Retrieved 1984.
• 7、 Hosoya, Takamitsu,Inouye, Satoshi,Nakamura, Mitsuhiro. "Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin". . . Retrieved 2022/01/19.