3,4-Dimethoxy-L-phenylalanine

Base Information

• Chemical Name: 3,4-Dimethoxy-L-phenylalanine
• CAS No.: 32161-30-1
• Molecular Formula: C11H15NO4
• Molecular Weight: 225.244
• Hs Code.: 29224999
• European Community (EC) Number: 928-902-8,626-580-0
• UNII: GC6UEI64EC
• DSSTox Substance ID: DTXSID00185947
• Nikkaji Number: J41.170A
• Wikidata: Q27279027
• Mol file: 32161-30-1.mol

Synonyms:32161-30-1;3,4-Dimethoxy-L-phenylalanine;(S)-2-Amino-3-(3,4-dimethoxyphenyl)propionic acid;3-(3,4-Dimethoxyphenyl)-L-alanine;L-3,4-Dimethoxyphenylalanine;L-Veratrylglycine;3,4-Dimethoxyphenylalanine, L-;L-Dimethoxyphenylalanine;(S)-2-Amino-3-(3,4-Dimethoxy-Phenyl)-Propionic Acid;3-METHOXY-O-METHYL-L-TYROSINE;(2S)-2-amino-3-(3,4-dimethoxyphenyl)propanoic acid;(S)-3,4-Dimethoxyphenylalanine;UNII-GC6UEI64EC;GC6UEI64EC;L-Tyrosine, 3-methoxy-O-methyl-;3,4-Dimethoxyphenylalanine;Alanine, 3-(3,4-dimethoxyphenyl)-, L-;(S)-2-amino-3-(3,4-dimethoxyphenyl)propanoic acid;beta-(3,4-Dimethoxyphenyl)-L-alanine;Levodopa impurity, 1-veratrylglycine- [USP];NSC-12199;MFCD01321274;SCHEMBL159001;H-Tyr(3-OMe,4-Me)-OH;DTXSID00185947;(L)-3,4-Dimethoxyphenyl alanine;VWTFNYVAFGYEKI-QMMMGPOBSA-N;(R)-b-(3,4-dimethoxyphenyl)alanine;(S)-b-(3,4-dimethoxyphenyl)alanine;AKOS007930123;AKOS010367899;AC-9278;CS-W008157;DS-1544;3-(3,4-Dimethoxyphenyl)-L-alanine, 97%;.BETA.-(3,4-DIMETHOXYPHENYL)-L-ALANINE;EN300-6472429;A821179;J-502409;Q27279027;L-3,4-Dimethoxyphenyl alanine L-Phe(3,4-Dimethoxy)-OH;(S)-2-Amino-3-(3 pound not4-dimethoxy-phenyl)-propionic acid;LEVODOPA IMPURITY, 1-VERATRYLGLYCINE- [USP IMPURITY]

Chemical Property of 3,4-Dimethoxy-L-phenylalanine

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 254-257 °C(lit.)
• Refractive Index: 1.547
• Boiling Point: 374.3 °C at 760mmHg
• PKA: 2.23±0.20(Predicted)
• Flash Point: 180.2°C
• PSA: 81.78000
• Density: 1.214 g/cm³
• LogP: 1.35850
• Storage Temp.: Store at 0°C
• Sensitive.: Air Sensitive
• Solubility.: Aqueous Acid (Slightly, Heated Sonicated), Aqueous Base (Slightly), Water (Sligh
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 225.10010796
• Heavy Atom Count: 16
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

3-(3,4-Dimethoxyphenyl)-L-alanine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC(C(=O)O)N)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)C[C@@H](C(=O)O)N)OC
• Uses: DOPA intermediate. 3-(3,4-Dimethoxyphenyl)-L-alanine can be used as a reactant to synthesize (2S)-2-amino-3-[3,4-di(methoxy)phenyl]propan-1-ol (β-amino alcohol) for use as a key intermediate to prepare tetracyclic core of the Erythrina alkaloids. DOPA intermediate

Technology Process of 3,4-Dimethoxy-L-phenylalanine

There total 19 articles about 3,4-Dimethoxy-L-phenylalanine 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: 89.6%

3,4-dimethoxyphenylpyruvic acid (2460-33-5) → (S)-3,4-dimethoxyphenylalanine (32161-30-1)

Guidance literature:

With L-Aspartic acid; pyridoxal 5'-phosphate; sodium hydroxide; In water; for 12h; pH=8; Reagent/catalyst; enantioselective reaction; Inert atmosphere; Microbiological reaction; Industrial scale;

DOI:10.1016/j.catcom.2018.10.033

Reference yield: 85.0%

(1S,2S,5S,9S)-5-(3,4-Dimethoxy-benzyl)-2,10,10-trimethyl-3-oxa-6-aza-tricyclo[7.1.1.02,7]undec-6-en-4-one (141895-41-2) → (S)-3,4-dimethoxyphenylalanine (32161-30-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 70 ℃; for 3h;

DOI:10.1016/S0957-4166(00)80263-3

Reference yield: 75.3%

N-acetyl-3,4-dimethoxyphenylalanine (27313-65-1) → (S)-3,4-dimethoxyphenylalanine (32161-30-1)

Guidance literature:

With hydrogenchloride; In water; at 95 - 100 ℃; for 6h;

DOI:10.1080/00397911.2012.748075

upstream raw materials:

N-formyl-3,4-dimethoxy-L-phenylalanine

DL-5-(3,4-dimethoxybenzyl)hydantoin

(S)-3-(3,4-Dimethoxy-phenyl)-2-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2Z)-ylideneamino]-propionic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

(1S,2S,5S,9S)-5-(3,4-Dimethoxy-benzyl)-2,10,10-trimethyl-3-oxa-6-aza-tricyclo[7.1.1.0^2,7]undec-6-en-4-one

Downstream raw materials:

N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-3-methoxy-O-methyl-L-tyrosine

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid

(S)-(+)-3,4-dimethoxyphenylalanine ethyl ester

(2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol

Refernces

• 1、 Yu, Jinhai,Li, Jing,Cao, Shuangyan,Wu, Ting,Zeng, Shuiyun,Zhang, Hongjuan,Liu, Junzhong,Jiao, Qingcai. "Chemoenzymatic synthesis of L-3,4-dimethoxyphenyl-alanine and its analogues using aspartate aminotransferase as a key catalyst". . p. 28 - 32. Retrieved 2018/11/26.
• 2、 Dickner, Tim,Laschat, Sabine. "Pictet-Spengler cyclization vs. Aminal formation: Competing reaction pathways of benzo[b][1,7]naphthyridines controlled by the configuration". . p. 2064 - 2070. Retrieved 2007/10/03.