Adrenochrome

Base Information

• Chemical Name: Adrenochrome
• CAS No.: 54-06-8
• Molecular Formula: C9H9 N O3
• Molecular Weight: 179.175
• Hs Code.: 2933990090
• European Community (EC) Number: 200-192-8
• NSC Number: 383491,407840
• UNII: 70G54NQL71
• DSSTox Substance ID: DTXSID00871530
• Nikkaji Number: J26.084C
• Wikipedia: Adrenochrome
• Wikidata: Q366835
• Metabolomics Workbench ID: 42126
• ChEMBL ID: CHEMBL1314174
• Mol file: 54-06-8.mol

Synonyms:Adrenochrome

Chemical Property of Adrenochrome

Chemical Property:

• Vapor Pressure: 3.67E-07mmHg at 25°C
• Melting Point: 115-120°C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 375.1°C at 760 mmHg
• PKA: 13.31±0.20(Predicted)
• Flash Point: 180.7°C
• PSA: 57.61000
• Density: 1.42g/cm³
• LogP: -0.80730
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly), Water
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 354

Purity/Quality:

99%, ^*data from raw suppliers

D,L-Adrenochrome ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CC(C2=CC(=O)C(=O)C=C21)O
• Uses: The substance mainly responsible for the red colours produced during the mild oxidation of adrenaline Adrenochrome is a derivative of epinephrine. When complexed with a salicylate, its stability is increased (carbazochrome). It was claimed to reduce blood loss, but the evidence is sparse.

Technology Process of Adrenochrome

There total 11 articles about Adrenochrome 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:

Epinephrine (329-65-7,51028-73-0) → adrenochrome (54-06-8)

Guidance literature:

With potassium hexacyanoferrate(III); In water; acetic acid; at 5 ℃; for 0.0833333h;

DOI:10.1248/cpb.29.1935

Reference yield:

bismuth oxycarbonate (BiO)2 CO3 + epinephrine hydrochloride (55-31-2,66240-90-2) → adrenochrome (54-06-8)

Guidance literature:

With ammonium persulfate; sodium hydrogencarbonate; In hydrogenchloride; water;

Reference yield:

L-epinephrine (51-43-4,51028-73-0) → adrenochrome (54-06-8)

Guidance literature:

With sodium hydroxide; In water; at 25 ℃; Concentration; Kinetics; Mechanism;

DOI:10.1007/s11243-012-9675-3

upstream raw materials:

Epinephrine

adrenaline o-quinone

L-epinephrine

epinephrine hydrochloride

Downstream raw materials:

(R)-Adrenochrome monobenzoylhydrazone

[(3R,3aR)-5-(Benzoyl-hydrazono)-3-hydroxy-1-methyl-6-oxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl]-acetic acid

(+/-)-trans-3a-(β-carboxyethylthio)-3a,4-dihydroadrenochrome monobenzoylhydrazone

Carbazochrome

Refernces

• 1、 Gorczyński, Adam,Kubicki, Maciej,Szymkowiak, Klaudia,?uczak, Teresa,Patroniak, Violetta. "Utilization of a new gold/Schiff-base iron(iii) complex composite as a highly sensitive voltammetric sensor for determination of epinephrine in the presence of ascorbic acid". . p. 101888 - 101899. Retrieved 2016.
• 2、 Beaupre, Brett A.,Hoag, Matthew R.,Moran, Graham R.. "Renalase does not catalyze the oxidation of catecholamines". . p. 62 - 66. Retrieved 2015.
• 3、 Al-Ayed, Abdullah S.,Al-Lohedan, Hamad A.,Rafiquee,Ali, Mohd Sajid,Issa, Zuheir A.. "Kinetics of the autoxidation of adrenaline and [copper(II)(adrenaline)] 2+ in alkaline aqueous and micellar media". . p. 173 - 181. Retrieved 2013.