(2S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate
• CAS No.: 59-92-7
• Molecular Formula: C9H11NO4
• Molecular Weight: 197.191
• Hs Code.: 29225090
• Mol file: 59-92-7.mol

Synonyms:(2S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate;L-dihydroxy-phenylalanine;L-dopa zwitterion;(2S)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate;CHEBI:57504

Chemical Property of (2S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate

Chemical Property:

• Appearance/Colour: colorless crystalline powder
• Vapor Pressure: 7.97E-09mmHg at 25°C
• Melting Point: 276-278 °C(lit.)
• Refractive Index: -12 ° (C=5, 1mol/L HCl)
• Boiling Point: 448.4 °C at 760 mmHg
• PKA: 2.32(at 25℃)
• Flash Point: 225 °C
• PSA: 103.78000
• Density: 1.468 g/cm³
• LogP: 0.75250
• Storage Temp.: 2-8°C
• Solubility.: Slightly soluble in water, practically insoluble in ethanol (96 per cent). It is freely soluble in 1 M hydrochloric acid and sparingly soluble in 0.1 M hydrochloric acid .
• Water Solubility.: Slightly soluble in water, dilute hydrochloric acid and formic acid. Insoluble in ethanol.
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 197.06880783
• Heavy Atom Count: 14
• Complexity: 204

Purity/Quality:

≥99% ^*data from raw suppliers

Levodopa ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)[O-])[NH3+])O)O
• Isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)[O-])[NH3+])O)O
• Parkinson's Disease Treatment: Levodopa (L-dopa) is the most effective medical therapy for the symptomatic treatment of Parkinson's disease (PD), which is characterized by the degeneration of dopaminergic neurons in the substantia nigra pars compacta, leading to decreased striatal dopamine levels and motor symptoms such as muscle rigidity, bradykinesia, and resting tremor.
• Motor and Non-Motor Complications: In the advanced stages of PD, patients receiving higher doses of levodopa are at risk of developing motor and non-motor complications, including dyskinesia and motor/non-motor fluctuations, in a dose-dependent manner.
• Pharmacotherapeutic Armamentarium: Various drugs and delivery systems have been developed for PD treatment, including oral, transdermal, inhaled, sublingual, intrajejunal, and subcutaneous routes of administration. These include levodopa, dopamine agonists, MAO-B inhibitors, COMT inhibitors, NMDA-type glutamate receptor antagonists, anticholinergics, and selective adenosine A2A receptor antagonists.
• Levodopa Equivalent Dose (LED): To compare the intensities of antiparkinsonian medication across different study cohorts, LED was introduced, with 100 mg of levodopa as the benchmark drug. LED provides a total score of antiparkinsonian medication, facilitating comparison across populations.
• New Drugs and Formulations: New antiparkinsonian drugs with established and novel mechanisms of action, such as safinamide, istradefylline, and opicapone, have been introduced. Novel formulations of existing drugs, such as inhaled levodopa and sublingual apomorphine, have also been developed.
• Levodopa Challenge Test (LCT): LCT is a safe and easy procedure used by clinicians for various indications in PD management, from preoperative evaluation for deep brain stimulation to medication adjustments to address motor or non-motor fluctuations and dyskinesias.
• Biological Synthesis of Levodopa: Levodopa is produced from the amino acid phenylalanine through a two-step enzymatic reaction involving phenylalanine hydroxylase (PhH) and tyrosine hydroxylase (TH). Levodopa is a precursor to dopamine, further metabolized into other compounds like 3-methoxy-tyramine, DOPAC, and HVA by enzymes like COMT and MAO.
• Absorption and Distribution: After oral ingestion, levodopa is absorbed mainly in the duodenum and proximal jejunum through a facilitated transport system for large neutral amino acids (LNAA). In the intestinal mucosa, levodopa is converted into dopamine by aromatic L-amino acid decarboxylase (AADC), which is also found in other organs such as the kidneys, liver, and brain.

Technology Process of (2S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate

There total 70 articles about (2S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate 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: 98.7%

(S)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid (7423-93-0) → levodopa (59-92-7,90638-38-3)

Guidance literature:

(S)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid; With sodium nitrate; 2-Methylcyclohexanol; N-bromoacetamide; at 56 ℃; for 2.16667h;

With nickel dichloride; at 25 ℃; for 4h; Temperature;

Reference yield: 96.0%

S,S-m-methoxy-p-acetoxy-N-acetylphenylalanine α-phenylethylamide (68706-13-8) → levodopa (59-92-7,90638-38-3)

Guidance literature:

With hydrogen bromide;

DOI:10.1007/BF01141713

Reference yield: 87.0%

C17H19NO5 → levodopa (59-92-7,90638-38-3)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; at 45 ℃; for 7h; Reagent/catalyst; Temperature; Solvent; Green chemistry;

upstream raw materials:

L-tyrosine

dopa

L-phenylalanine

L-dopaquinone

Downstream raw materials:

L-dopa methyl ester hydrochloride

C₁₂H₃₀N₆*C₉H₁₁NO₄*3H⁽¹⁺⁾

L-3-carboxy-7,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

ethyl (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate hydrochloride

Refernces

• 1、 Chen, Huei-Yu,Yeh, Yi-Chun. "Detection of tyrosine and monitoring tyrosinase activity using an enzyme cascade-triggered colorimetric reaction". . p. 29745 - 29750. Retrieved 2020.
• 2、 Eser, Bekir E.,Fitzpatrick, Paul F.. "Measurement of intrinsic rate constants in the tyrosine hydroxylase reaction". . p. 645 - 652. Retrieved 2010.
• 3、 Min, Kyoungseon,Kathavarayan, Thenmozhi,Park, Kyungmoon,Yoo, Young Je. "Novel strategy for enhancing productivity in l-DOPA synthesis: The electroenzymatic approach using well-dispersed l-tyrosine". . p. 87 - 90. Retrieved 2013.
• 4、 Morimura, Keiji,Hiramatsu, Kenji,Yamazaki, Chihiro,Hattori, Yasunao,Makabe, Hidefumi,Hirota, Mitsuru. "Daedalin A, a metabolite of daedalea dickinsii, inhibits melanin synthesis in an in vitro human skin model". . p. 627 - 632. Retrieved 2009.
• 5、 Sih et al.. "". . p. 6204. Retrieved 1969.
• 6、 Aich, Pulakesh,An, Jaeyeon,Yang, Byeongseon,Ko, Young Ho,Kim, Junghyun,Murray, James,Cha, Hyung Joon,Roh, Joon Ho,Park, Kyeng Min,Kim, Kimoon. "Self-assembled adhesive biomaterials formed by a genetically designed fusion protein". . p. 12642 - 12645. Retrieved 2018.
• 7、 Shin, Inchul,Davis, Ian,Nieves-Merced, Karinel,Wang, Yifan,McHardy, Stanton,Liu, Aimin. "A novel catalytic heme cofactor in SfmD with a single thioether bond and abis-His ligand set revealed by ade novocrystal structural and spectroscopic study". . p. 3984 - 3998. Retrieved 2021/04/06.