2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Base Information

• Chemical Name: 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
• CAS No.: 492-46-6
• Molecular Formula: C9H11NO5
• Molecular Weight: 213.19
• European Community (EC) Number: 803-796-5
• DSSTox Substance ID: DTXSID80860306
• Nikkaji Number: J2.543.689J
• ChEMBL ID: CHEMBL1593851
• Mol file: 492-46-6.mol

Synonyms:492-46-6;2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid;H-DL-beta-(3,4-Dihydroxyphenyl)-DL-Ser-OH;(2RS,3RS)-2-AMINO-3-(3,4-DIHYDROXY-PHENYL)-3-HYDROXY-PROPIONIC ACID;(2RS,3RS)-2-Amino-3-(3,4-dihydroxy-phenyl)-3-hydroxy-propionic acid;DL-DOPS;DL-Droxidopa;Droxidopa [INN:JAN];3,4-Dihydroxyphenylserine;C9H11NO5;L-DOPS;DOPS;SM5688;Dioxyphenylserin;DL-Tyrosine, .beta.,3-dihydroxy-;threo-DOPS;NCGC00164537-01;Serine, 3-(3,4-dihydroxyphenyl)-, DL-;L-Tyrosine, beta,3-dihydroxy-, (beta-R)-;(-)-threo-3-(3,4-Dihydroxyphenyl)-L-serine;3,4-threo-DOPS;Serine, 3-(3,4-dihydroxyphenyl)-, L-threo-;SCHEMBL129758;CHEMBL1593851;DTXSID80860306;erythro-3,4-Dihydroxyphenylserine;MFCD00004266;AKOS003381879;NCGC00164537-02;AC-27646;H-DL-b-(3,4-Dihydroxyphenyl)-DL-Ser-OH;LS-145006;CS-0267961;FT-0651749;FT-0667809;EN300-1848159;alpha-Amino-beta,3,4-trihydroxybenzenepropionic acid

Chemical Property of 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Chemical Property:

• Vapor Pressure: 6.39E-13mmHg at 25°C
• Melting Point: 219-221 °C
• Boiling Point: 549.8°Cat760mmHg
• PKA: 2.09±0.24(Predicted)
• Flash Point: 286.3°C
• Density: 1.608g/cm³
• Storage Temp.: ?20°C
• Solubility.: 0.1 M HCl: soluble (Solutions should be freshly prepared.)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 213.06372245
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

95% ^*data from raw suppliers

DL-3,4-Dihydroxyphenylserine ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(C(C(=O)O)N)O)O)O

Technology Process of 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

There total 9 articles about 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic 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: 90.5%

→ 3-(3,4-dihydroxyphenyl)serine (492-46-6) + L-threo-3-(3,4-dihydroxyphenyl)serine (34047-62-6)

Guidance literature:

Reference yield:

3,4-dibenzyloxybenzaldehyde (5447-02-9) → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq.-ethanolic NaOH / anschliessendes Erwaermen mit wss. HCl

2: palladium; aqueous methanol / Hydrogenation

With methanol; sodium hydroxide; palladium;

Reference yield:

D,L-threo-3-(3,4-Dibenzyloxyphenyl)serine (55449-18-8,55449-19-9,55637-52-0,70543-77-0,70561-66-9,106887-48-3,113139-65-4,124709-63-3,146985-69-5) → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

With methanol; palladium; Hydrogenation;

upstream raw materials:

D,L-threo-3-(3,4-Dibenzyloxyphenyl)serine

3,4-dibenzyloxybenzaldehyde

3,4-bis(ethoxycarboxy)-benzaldehyde

(2RS.3RS)-2-amino-3-(3,4-bis-benzyloxy-phenyl)-3-hydroxy-propionic acid

Refernces