(2S)-2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid

Base Information

• Chemical Name: (2S)-2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid
• CAS No.: 23508-35-2
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 2918290000
• European Community (EC) Number: 676-144-9
• UNII: 3X3113D870
• DSSTox Substance ID: DTXSID60432803
• Nikkaji Number: J70.493H
• Wikidata: Q27466783
• ChEMBL ID: CHEMBL1162490
• Mol file: 23508-35-2.mol

Synonyms:23508-35-2;(S)-2-hydroxy-3-(4-hydroxyphenyl)propanoic acid;(S)-3-(4-Hydroxyphenyl)-2-hydroxypropionic acid;(2S)-2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid;(s)-3-(4-hydroxyphenyl)lactic acid;Latifolicinin C acid;L-p-Hydroxyphenyllactic acid;CHEMBL1162490;p-Hydroxyphenyl lactic acid, L-;(2s)-3-(4-hydroxyphenyl)-2-hydroxypropionic acid;(s)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid;(+)-3-(4-Hydroxyphenyl)lactic acid;3X3113D870;2-Hydroxy-3-(4-hydroxy-phenyl)-propionic acid;TYF;Benzenepropanoic acid, alpha,4-dihydroxy-, (alphaS)-;SCHEMBL1067448;DTXSID60432803;(s)-3-p-hydroxyphenyllactic acid;JVGVDSSUAVXRDY-QMMMGPOBSA-N;UNII-3X3113D870;BDBM50412191;MFCD01632461;AKOS016843267;AS-35397;HY-136593;CS-0131956;(S)-2-hydroxy-3-(4-hydroxyphenyl)propanoicacid;(S)-3-(4-hydroxyphenyl)-2-hydroxypropanoic acid;(s)-3-(4'-hydroxyphenyl)-2-hydroxy-propanoic acid;(2S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid;Q27466783;BENZENEPROPANOIC ACID, .ALPHA.,4-DIHYDROXY-, (.ALPHA.S)-

Chemical Property of (2S)-2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165-168 °C
• Refractive Index: 1.617
• Boiling Point: 414.439 °C at 760 mmHg
• PKA: 3.80±0.10(Predicted)
• Flash Point: 218.597 °C
• PSA: 77.76000
• Density: 1.405 g/cm³
• LogP: 0.38020
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 173

Purity/Quality:

≥97%,≥99%, ^*data from raw suppliers

(S)-3-(4-Hydroxyphenyl)-2-hydroxypropionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)O)O

Technology Process of (2S)-2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid

There total 40 articles about (2S)-2-Hydroxy-3-(4-hydroxyphenyl)propanoic 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: 94.0%

4-hydroxyphenylpiruvic acid (156-39-8) → 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid (6482-98-0,23508-35-2,89919-57-3,306-23-0) + ?Tyr (556-02-5,556-03-6,34537-57-0,55520-40-6,96946-98-4,60-18-4,18875-48-4,25619-78-7,30704-25-7)

Guidance literature:

With [Ir(III)Cp*(bpy)(OH₂)](SO₄); ammonium formate; In water; at 80 ℃; for 24h; pH=5.0;

DOI:10.1021/ja031633r

Reference yield: 92.0%

4-hydroxyphenylpiruvic acid (156-39-8) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Guidance literature:

With triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2008.01.067

Reference yield: 80.0%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 4-hydroxyphenylpiruvic acid (156-39-8) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Guidance literature:

With formate dehydrogenase; oxygen; ammonium formate; NADH; In aq. phosphate buffer; at 21 ℃; for 7h; under 750.075 Torr; pH=7; Concentration; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/chem.201403195

upstream raw materials:

4-hydroxyphenylpiruvic acid

(p-aminophenyl)alanine

2-hydroxy-3-(4-hydroxyphenyl)acrylic acid

methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate

Downstream raw materials:

(+/-)-2-hydroxy-3-(4-hydroxy-3,5-diiodo-phenyl)-propionic acid

(+/-)-2-hydroxy-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid

2-hydroxy-3-(4-hydroxy-3-nitro-phenyl)-propionic acid

4-hydroxyphenylpiruvic acid

Refernces

• 1、 Sasaki,Otsuka. "-". . p. 535. Retrieved 1917.
• 2、 Qiu, Fei,Yang, Chunxian,Yuan, Lina,Xiang, Dan,Lan, Xiaozhong,Chen, Min,Liao, Zhihua. "A Phenylpyruvic Acid Reductase Is Required for Biosynthesis of Tropane Alkaloids". . p. 7807 - 7810. Retrieved 2018.
• 3、 Ji, Xinjian,Liu, Wan-Qiu,Yuan, Shuguang,Yin, Yue,Ding, Wei,Zhang, Qi. "Mechanistic study of the radical SAM-dependent amine dehydrogenation reactions". . p. 10555 - 10558. Retrieved 2016/09/02.