(S)-adrenaline

Base Information

• Chemical Name: (S)-adrenaline
• CAS No.: 150-05-0
• Molecular Formula: C9H13 N O3
• Molecular Weight: 183.207
• European Community (EC) Number: 205-752-5
• NSC Number: 62786
• UNII: NA71GR3TNV
• DSSTox Substance ID: DTXSID301047668
• Nikkaji Number: J10.982G
• Wikidata: Q27074317
• Pharos Ligand ID: YGMKNG3ZHNHD
• Metabolomics Workbench ID: 52262
• ChEMBL ID: CHEMBL42280
• Mol file: 150-05-0.mol

Synonyms:Adrenaline Hydrochloride, Racemic Mixture;Adrenaline, Racemic;Adrenaline, Racemic Mixture;Epinephrine Hydrochloride, Racemic Mixture;Epinephrine, Racemic;Epinephrine, Racemic Mixture;Micronefrin;Micronephrine;Racemic Adrenaline;Racemic Epinephrine;Racemic Mixture Adrenaline;Racemic Mixture Epinephrine;Racepinephrine;Racepinephrine Hydrochloride;Vaponefrin

Chemical Property of (S)-adrenaline

Chemical Property:

• Vapor Pressure: 1.45E-07mmHg at 25°C
• Melting Point: 211.5°C
• Refractive Index: 1.4760 (estimate)
• Boiling Point: 413.1°Cat760mmHg
• PKA: 9.60±0.10(Predicted)
• Flash Point: 207.9°C
• PSA: 72.72000
• Density: 1.283g/cm³
• LogP: 0.74150
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 183.08954328
• Heavy Atom Count: 13
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

D-(+)-Epinephrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC(C1=CC(=C(C=C1)O)O)O
• Isomeric SMILES: CNC[C@H](C1=CC(=C(C=C1)O)O)O
• Recent ClinicalTrials: The Clinical Validity and Safety of IOP Injection MRI Contrast Agent in Hepatocellular Carcinoma
• Uses: D-(+)-Epinephrine is a stereoisomer of Epinephrine, a natural neurotransmitter that is released from the adrenal medulla and activates adrenoceptors.

Technology Process of (S)-adrenaline

There total 7 articles about (S)-adrenaline 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: 54.5%

S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-methylamido-ethan (104819-58-1,104873-32-7,104873-33-8) → (S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol (150-05-0,51028-73-0)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87372-5

Reference yield: 5.0%

adrenalone (99-45-6) → C18H24N2O6 + L-epinephrine (51-43-4,51028-73-0) + (S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol (150-05-0,51028-73-0)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In N,N-dimethyl-formamide; isopropyl alcohol; Title compound not separated from byproducts.; Electrochemical reaction;

Reference yield:

Epinephrine (329-65-7,51028-73-0) → L-epinephrine (51-43-4,51028-73-0) + (S)-4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol (150-05-0,51028-73-0)

Guidance literature:

With core-shell macrocyclic glycopeptide-based chiral stationary phase NicoShell; In methanol; acetic acid; acetonitrile; at 20 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/chir.22985

upstream raw materials:

adrenalone

1-(3,4-dihydroxyphenyl)-1-oxo-2-methylamino-ethan-hydrochlorid

S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-methylamido-ethan

L-Tartaric acid

Downstream raw materials:

Epinephrine

Refernces

• 1、 Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.. "Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase". . p. 1067 - 1078. Retrieved 2018/08/01.
• 2、 Muller,Keil,Gerhard. "Enantiomers of 2,2'-dinitrobiphenyl-6,6'-dicarboxylic acid as stereoselective reversible protective groups. I. Stereospecificity of syntheses of S-(+)- and R-(-)-noradrenalin and adrenalin". . p. 1529 - 1532. Retrieved 2007/10/02.