(2R,3S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate

Base Information

• Chemical Name: (2R,3S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate
• CAS No.: 23651-95-8
• Molecular Formula: C₉H₁₁NO₅
• Molecular Weight: 213.19
• Hs Code.: 29225090
• Mol file: 23651-95-8.mol

Synonyms:

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

Chemical Property:

• Vapor Pressure: 6.39E-13mmHg at 25°C
• Melting Point: 232-235° (dec); mp 229-232° (dec) (Ohashi)
• Refractive Index: 1.692
• Boiling Point: 549.8 °C at 760mmHg
• PKA: 2.09±0.24(Predicted)
• Flash Point: 286.3 °C
• PSA: 124.01000
• Density: 1.608 g/cm³
• LogP: 0.24340
• Storage Temp.: ?20°C
• Solubility.: DMSO: ≥3mg/mL
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 213.06372245
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

99%MIN ^*data from raw suppliers

L-threo-Droxidopa ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• 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-])[NH3+])O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@@H]([C@H](C(=O)[O-])[NH3+])O)O)O
• Description: Droxidopa is a synthetic amino acid precursor of (-)-norepinephrine which is absorbed from the gut and metabolized to norepinephrine. In Parkinsonian patients, droxidopa added to existing levodopa/decarboxylase inhibitor therapy produces significant improvements in retropulsion, dysarthria and muscular rigidity refractory to other treatments; however, tremor was unaffected. Droxidopa (L-DOPS) is a synthetic precursor and prodrug of the neurotransmitter norepinephrine. It is transformed into norepinephrine through the action of DOPA decarboxylase. L-DOPS increases norepinephrine levels in the rat heart following intraperitoneal administration and in the brain following intracerebroventricular administration at doses of 125 and 100 μg/animal, respectively. It increases arterial pressure and mesenteric arterial resistance in rats with ligated portal vein or biliary ducts when used at doses of 25-50 mg/kg. L-DOPS crosses the blood brain barrier, however, its effects can be blocked by the peripherally-restricted DOPA decarboxylase inhibitor carbidopa , indicating that the mechanism is peripheral. Formulations containing droxidopa are used in the treatment of neurogenic orthostatic hypotension.
• Uses: The L-threo-form Droxidopa. A synthetic amino acid precursor of Norepinephrine (N674500). Antiparkinsonian. Droxidopa is a psychoactive drug and acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline). L-DOPS has been administered for clinical trial studies in mice with amyloid pathology.

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

There total 6 articles about (2R,3S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate 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:

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;

Reference yield:

(2RS:3SR)-2-amino-3-hydroxy-3-(3,4-bis-ethoxycarbonyloxy-phenyl)-propionic acid ethyl ester → (+/-)-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 alkaline solution;

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