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54-06-8

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54-06-8 Usage

Uses

Different sources of media describe the Uses of 54-06-8 differently. You can refer to the following data:
1. The substance mainly responsible for the red colours produced during the mild oxidation of adrenaline
2. 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.

Purification Methods

It was crystallised from MeOH/formic acid, as red crystals of the hemihydrate, and stored in a vacuum desiccator. The mono-semicarbazone (Carbazochrome) [69-81-8] M 236.2, crystallises as orange-red crystals from dilute EtOH with m ~203o (dec) and is haemostatic. [Heacock Chem Rev 59 181 1959, Beilstein 21 III/IV 6434.]

Check Digit Verification of cas no

The CAS Registry Mumber 54-06-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 4 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 54-06:
(4*5)+(3*4)+(2*0)+(1*6)=38
38 % 10 = 8
So 54-06-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3/t9-/m0/s1

54-06-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Hydroxy-1-methyl-5,6-indolinedione

1.2 Other means of identification

Product number -
Other names 1H-Indole-5,6-dione, 2,3-dihydro-3-hydroxy-1-methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:54-06-8 SDS

54-06-8Synthetic route

Epinephrine
329-65-7

Epinephrine

A

adrenolutine
642-75-1

adrenolutine

B

adrenochrome
54-06-8

adrenochrome

Conditions
ConditionsYield
In water-d2 at 24.9℃; for 5.83333h; Rate constant; Mechanism; Irradiation; other sensitizers: methylene blue, rose bengal, fluoresceine, superoxide dismutase; other inhibitors: 1,3-diphenylisobenzofuran, 1,4-diazobicyclo<2,2,2>octane, KN3, NaN3; other solvent: H2O.;
Epinephrine
329-65-7

Epinephrine

A

adrenaline o-quinone
672-73-1, 162706-73-2

adrenaline o-quinone

B

adrenochrome
54-06-8

adrenochrome

Conditions
ConditionsYield
Product distribution; Irradiation; laser induced oxidation at pH=5 at various electrodes; half life of 0-quinone;
adrenaline o-quinone
672-73-1, 162706-73-2

adrenaline o-quinone

adrenochrome
54-06-8

adrenochrome

Conditions
ConditionsYield
Rate constant; the half life;
Epinephrine
329-65-7

Epinephrine

adrenochrome
54-06-8

adrenochrome

Conditions
ConditionsYield
With potassium hexacyanoferrate(III) In water; acetic acid at 5℃; for 0.0833333h;
With air; mushroom tyrosinase at 23℃; for 0.333333h; phosphate buffer pH=6.8;
With D,L-N-acetyl-N-nitrosotryptophan at 37℃; for 0.5h;
L-epinephrine
51-43-4

L-epinephrine

adrenochrome
54-06-8

adrenochrome

Conditions
ConditionsYield
With pseudooctahedral quaterpyridineiron(III) complex bound to sodium poly(L-glutamate); dihydrogen peroxide at 25.9℃; Kinetics; Thermodynamic data; Mechanism; 0.05 M Tris buffer pH 7, further temperatures, ΔH(excit.), ΔS(excit.), further reagent, electron-transfer;
bismuth oxycarbonate (BiO)2 CO3

bismuth oxycarbonate (BiO)2 CO3

epinephrine hydrochloride
55-31-2

epinephrine hydrochloride

adrenochrome
54-06-8

adrenochrome

Conditions
ConditionsYield
With ammonium persulfate; sodium hydrogencarbonate In hydrogenchloride; water
L-epinephrine
51-43-4

L-epinephrine

adrenochrome
54-06-8

adrenochrome

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; Kinetics; Mechanism; Concentration;
With dihydrogen peroxide; sodium sulfate Reagent/catalyst;
With human renalase variant 1; Β-NADH In aq. phosphate buffer at 25℃; pH=7.5; Reagent/catalyst; Enzymatic reaction;
With gold electrode modied with [Fe2(H3L)2(MeOH)2(μ-OMe)2](ClO4)4 Reagent/catalyst; Michael Addition; Electrochemical reaction;
5,6-0-isopropylidene ascorbic acid
860649-42-9

5,6-0-isopropylidene ascorbic acid

acetic anhydride
108-24-7

acetic anhydride

adrenochrome
54-06-8

adrenochrome

(5aΞ,8R)-5a,8a-diacetoxy-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-(5ar,8ac)-8,8a-dihydro-1H,5aH-furo[3',4':5,6][1,4]dioxino[2,3-f]indol-6-one

(5aΞ,8R)-5a,8a-diacetoxy-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-(5ar,8ac)-8,8a-dihydro-1H,5aH-furo[3',4':5,6][1,4]dioxino[2,3-f]indol-6-one

Conditions
ConditionsYield
(i) acrylonitrile, (ii) /BRN= 385737/, Py, CHCl3; Multistep reaction;
adrenochrome
54-06-8

adrenochrome

C18H18N2O6
121769-77-5

C18H18N2O6

Conditions
ConditionsYield
In various solvent(s) at 27℃; for 4h; pH = 6.8;80 mg
N-(2-mercaptopropionyl)glycine
1953-02-2

N-(2-mercaptopropionyl)glycine

adrenochrome
54-06-8

adrenochrome

[2-((3R,3aR)-3-Hydroxy-1-methyl-5,6-dioxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl)-propionylamino]-acetic acid

[2-((3R,3aR)-3-Hydroxy-1-methyl-5,6-dioxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl)-propionylamino]-acetic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 0.5h;
acetic anhydride
108-24-7

acetic anhydride

adrenochrome
54-06-8

adrenochrome

5,6-diacetoxy-N-methyl indole
13988-19-7

5,6-diacetoxy-N-methyl indole

Conditions
ConditionsYield
With dmap; ascorbic acid 1) Phosphate buffer, diethyl ether, 15 min, 2) diethyl ether; Yield given. Multistep reaction;
acetic anhydride
108-24-7

acetic anhydride

adrenochrome
54-06-8

adrenochrome

A

5,6,5',6'-tetraacetoxy-1,1'-dimethyl-2,3'-biindolyl
116755-29-4

5,6,5',6'-tetraacetoxy-1,1'-dimethyl-2,3'-biindolyl

B

5,6-diacetoxy-1-methyl-3-(5',6'-diacetoxy-1'-methyl-2'-indolinyl)-indole
116755-28-3

5,6-diacetoxy-1-methyl-3-(5',6'-diacetoxy-1'-methyl-2'-indolinyl)-indole

C

adrenaline black
116755-27-2

adrenaline black

Conditions
ConditionsYield
With pyridine; hydrogenchloride; sodium dithionite 1.) 15 min; 2.) r.t., 12 h; Yield given. Multistep reaction. Yields of byproduct given;
acetic anhydride
108-24-7

acetic anhydride

adrenochrome
54-06-8

adrenochrome

adrenaline black
116755-27-2

adrenaline black

Conditions
ConditionsYield
With pyridine; sodium dithionite; water 1.) r.t., 48 h; 2.) r.t., 12 h; Yield given. Multistep reaction;
benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

mercaptoacetic acid
68-11-1

mercaptoacetic acid

adrenochrome
54-06-8

adrenochrome

A

(R)-Adrenochrome monobenzoylhydrazone
79697-36-2, 94460-23-8

(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
64728-92-3, 79697-34-0

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

Conditions
ConditionsYield
Product distribution; various temperatures, various reaction times;
benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

adrenochrome
54-06-8

adrenochrome

(+/-)-trans-3a-(β-carboxyethylthio)-3a,4-dihydroadrenochrome monobenzoylhydrazone
64728-91-2, 79697-29-3, 79697-30-6, 79697-35-1

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

(+/-)-cis-3a-(β-carboxyethylthio)-3a,4-dihydroadrenochrome monobenzoylhydrazone
64728-91-2, 79697-29-3, 79697-30-6, 79697-35-1

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

Conditions
ConditionsYield
Product distribution; various temperatures, various reaction times;
With hydrogenchloride; sodium hydroxide 1.) H2O, 5 deg C, 30 min, 2.) H2O, 0 deg C; Yield given. Multistep reaction;
mercaptoacetic acid
68-11-1

mercaptoacetic acid

adrenochrome
54-06-8

adrenochrome

((3R,3aR)-3-Hydroxy-1-methyl-5,6-dioxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl)-acetic acid

((3R,3aR)-3-Hydroxy-1-methyl-5,6-dioxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl)-acetic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 0.5h;
3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

adrenochrome
54-06-8

adrenochrome

3-((3R,3aR)-3-Hydroxy-1-methyl-5,6-dioxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl)-propionic acid

3-((3R,3aR)-3-Hydroxy-1-methyl-5,6-dioxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl)-propionic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 0.5h;
adrenochrome
54-06-8

adrenochrome

(R)-Adrenochrome monobenzoylhydrazone
79697-36-2, 94460-23-8

(R)-Adrenochrome monobenzoylhydrazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / H2O / 0.5 h / 25 °C
2: HCl / H2O / 0.5 h / 25 °C
View Scheme
adrenochrome
54-06-8

adrenochrome

(+/-)-trans-3a-(β-carboxyethylthio)-3a,4-dihydroadrenochrome monosemicarbazone
64728-94-5, 79697-31-7

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / H2O / 0.5 h / 25 °C
2: 30 percent / 8percent formic acid / H2O
View Scheme
adrenochrome
54-06-8

adrenochrome

[(3R,3aR)-5-(Benzoyl-hydrazono)-3-hydroxy-1-methyl-6-oxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl]-acetic acid
64728-92-3, 79697-34-0

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / H2O / 0.5 h / 25 °C
2: HCl / H2O / 0.5 h / 25 °C
View Scheme
adrenochrome
54-06-8

adrenochrome

{2-[5-(Benzoyl-hydrazono)-3-hydroxy-1-methyl-6-oxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl]-propionylamino}-acetic acid
64728-93-4

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / H2O / 0.5 h / 25 °C
2: HCl / H2O / 25 °C
View Scheme
adrenochrome
54-06-8

adrenochrome

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / H2O / 0.5 h / 25 °C
2: 21 percent / HCl / H2O
View Scheme
adrenochrome
54-06-8

adrenochrome

(+/-)-trans-3a-(β-carboxyethylthio)-3a,4-dihydroadrenochrome monobenzoylhydrazone
64728-91-2, 79697-29-3, 79697-30-6, 79697-35-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / H2O / 0.5 h / 25 °C
2: HCl / H2O / RT, 0 deg C
View Scheme

54-06-8Relevant articles and documents

Activation of H2O2 and superoxide production using a novel cobalt complex based on a polyampholyte

Lombardo Lupano, Lucía V.,Lázaro Martínez, Juan Manuel,Piehl, Lidia Leonor,Rubin De Celis, Emilio,Campo Dall'Orto, Viviana

, p. 342 - 354 (2013)

A new catalyst based on Co(II) and a hydrogel with property of polyampholyte was characterized by equilibrium studies of Co(II) uptake, solid-state NMR and energy dispersive X-ray analysis. The matrix derived from methacrylic acid and 2-methylimidazole is easily synthesized in one-spot strategy, and combines coordination properties with chemical resistance. The catalytic activity of this material on H2O2 activation was studied by electron spin resonance, which confirmed the release of superoxide radical. A possible mechanism of interaction involves the simultaneous production of dioxygen, protons and water. The catalytic performance was assessed in the activation of H2O2 for the oxidation of two representative organic compounds of environmental concern. About 70% of methyl orange, a model azo dye, was removed from distilled water in 2 h by oxidation with H2O2 60 mM and by adsorption on the catalyst. The amount of adsorbed dye was minimized in the presence of 0.1 M Na2SO4. The kinetics of the processes followed a pseudo-first-order empirical model, and the catalyst was recovered and re-used. Epinephrine was chosen as a pharmaceutical model susceptible to superoxide attack. About 80% of conversion to adrenochrome was reached in less than 6 min, following a pseudo-first-order kinetic model.

Kinetic studies on the manganese(II) complex catalyzed oxidation of epinephrine

Szigyártó, I.Cs.,Szabó,Simándi

, p. 66 - 71 (2013)

The manganese complex [Mn2(HL)2](BPh 4)2 was found to be a selective catalyst for the oxidation of epinephrine (a catecholamine derivative) to adrenochrome at room temperature in sodium carbonate-bicarbonate buffer. The epinephrine auto-oxidation rate significantly increases upon the addition of manganese complex. The kinetics of reaction was studied by spectrophotometric method, monitoring the increase in concentration of adrenochrome product. According to the proposed mechanism, O2 binding to the manganese complex is followed by the formation of a ternary catalyst-dioxygen-substrate complex as active intermediate, which decomposes in a rate-determining step, generating the adrenochrome.

The Oxovanadyl(IV) catalysed Oxidation of Adrenaline by Molecular Oxygen

Jameson, Reginald F.,Kiss, Tamas

, p. 1833 - 1838 (1986)

The oxidation of adrenaline (H2LH+) by molecular oxygen in the presence of catalytic amounts of VO2+ ions has been followed using a Clark-type oxygen electrode.The empirical rate law -d/dt = kobs. + p was obtained in which p is a small constant (only observable at low pH) and kobs. is given by the relationship (i), where T and T are total initial concentrations of (i) VO2+ and adrenaline respectively.It is demonstrated that this behaviour is consistent with the involvement of both VO2+ and V2+ species and furthermore that it also calls for the presence of a tris(adrenaline) species, V(LH)3+.A kinetically determined equilibrium constant for reaction (ii) is VO(LH)2 + H2LH+ V(LH)3+ + H2O (ii) reported.The necessary proton- and metal-ligand equilibrium constants were obtained by pH- and 1H n.m.r.-titration techniques.All solutions were made up to a constant ionic strength (I = 0.100 mol dm-3) with KNO3 at 25.00 +/- 0.02 deg C.

Production process of adrenal glands

-

, (2021/11/15)

The invention discloses a production technology for carbazochrome. The production technology comprises the following steps: 1) synthesizing chloracetyl catechol; 2) synthesizing corticosterone hydrochloride; 3) synthesizing adrenaline; and 4) synthesizing the carbazochrome. The production technology for the carbazochrome, disclosed by the invention, has the advantages of simple preparation method,few steps and easiness for operation and control; and an obtained product has good color and luster, good quality, high purity and high yield, can be directly used for production and utilization andhas very good practicability.

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