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37178-37-3

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37178-37-3 Usage

Uses

Different sources of media describe the Uses of 37178-37-3 differently. You can refer to the following data:
1. Antiparkisonian.
2. L-Dopa ethyl ester has been used to study the protective effects of piperlongumine (PLG) on rotenone-induced Parkinson disease (PD).

Biochem/physiol Actions

L-Dopa ethyl ester is a prodrug of levodopa that has greater gastric solubility. The drug is rapidly hydrolyzed to levodopa by nonspecific esterases in the gastrointestinal tract. L-Dopa ethyl ester (etilevodopa)-carbidopa treatment was well tolerated but did not demonstrate better efficacy compared with standard levodopa-carbidopa treatment. L-Dopa ethyl ester should have a significant brain penetration following an administration by injection.

Check Digit Verification of cas no

The CAS Registry Mumber 37178-37-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,7,1,7 and 8 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 37178-37:
(7*3)+(6*7)+(5*1)+(4*7)+(3*8)+(2*3)+(1*7)=133
133 % 10 = 3
So 37178-37-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H15NO4/c1-2-16-11(15)8(12)5-7-3-4-9(13)10(14)6-7/h3-4,6,8,13-14H,2,5,12H2,1H3/t8-/m0/s1

37178-37-3 Well-known Company Product Price

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  • Sigma

  • (SML0091)  L-Dopa ethyl ester  ≥98% (HPLC)

  • 37178-37-3

  • SML0091-5MG

  • 1,107.99CNY

  • Detail
  • Sigma

  • (SML0091)  L-Dopa ethyl ester  ≥98% (HPLC)

  • 37178-37-3

  • SML0091-25MG

  • 4,468.23CNY

  • Detail

37178-37-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 3-hydroxy-L-tyrosine ethyl ester

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:37178-37-3 SDS

37178-37-3Synthetic route

ethanol
64-17-5

ethanol

levodopa
59-92-7

levodopa

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

Conditions
ConditionsYield
With hydrogenchloride Fischer esterification;100%
With hydrogenchloride Fisher esterfication;100%
With thionyl chloride 1.) 0 deg C, 2 h, 2.) room temperature, overnight;
With thionyl chloride for 24h; Reflux;
levodopa
59-92-7

levodopa

ascorbic acid
50-81-7

ascorbic acid

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

Conditions
ConditionsYield
With thionyl chloride; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate; sodium sulfate In ethanol; water88%
With thionyl chloride; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate; sodium sulfate In ethanol; water88%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester
203398-44-1

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;97%
With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;97%
With triethylamine In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) room temperature, 48 h;42.1 g
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

levodopa
59-92-7

levodopa

Conditions
ConditionsYield
With water; sodium chloride In dimethyl sulfoxide at 37℃; Rate constant; also human plasma as reagent;
3-Bromoindan-1-one
40774-41-2

3-Bromoindan-1-one

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

3-(3,4-dihydroxyphenyl)-2-(3-oxoindan-1-ylamino)propionic acid ethyl ester

3-(3,4-dihydroxyphenyl)-2-(3-oxoindan-1-ylamino)propionic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine ethyl ester

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 42.1 g / triethylamine / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 48 h
2: 43 percent Turnov. / CF3CO2Ag, I2 / CH2Cl2 / 24 h / Ambient temperature
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

carbidopa monohydrate

carbidopa monohydrate

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

ethyl 3-(3,4-(dibenzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate
69344-36-1

ethyl 3-(3,4-(dibenzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2: potassium carbonate / acetone / 48 h / Reflux
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

ethyl 2-amino-3-(3,4-(dibenzyloxy)phenyl)propanoate
69295-27-8

ethyl 2-amino-3-(3,4-(dibenzyloxy)phenyl)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2: potassium carbonate / acetone / 48 h / Reflux
3: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

C23H22N2O3

C23H22N2O3

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2.1: potassium carbonate / acetone / 48 h / Reflux
3.1: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C
4.1: toluene / 24 h / Reflux
5.1: acetic acid; nitric acid / 1.5 h / 0 °C
5.2: 1.5 h / 80 °C
6.1: hydrazine hydrate / ethanol / 40 h / Reflux
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

C23H24N2O2

C23H24N2O2

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2.1: potassium carbonate / acetone / 48 h / Reflux
3.1: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C
4.1: toluene / 24 h / Reflux
5.1: acetic acid; nitric acid / 1.5 h / 0 °C
5.2: 1.5 h / 80 °C
6.1: hydrazine hydrate / ethanol / 40 h / Reflux
7.1: dimethyl sulfide borane / tetrahydrofuran / 30 h / Reflux
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

ethyl 3-(3,4-bis(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yl)propanoate

ethyl 3-(3,4-bis(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yl)propanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2: potassium carbonate / acetone / 48 h / Reflux
3: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C
4: toluene / 24 h / Reflux
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

(S)-2-(6,7-bis(benzyloxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)isoindoline-1,3-dione

(S)-2-(6,7-bis(benzyloxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2.1: potassium carbonate / acetone / 48 h / Reflux
3.1: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C
4.1: toluene / 24 h / Reflux
5.1: acetic acid; nitric acid / 1.5 h / 0 °C
5.2: 1.5 h / 80 °C
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

tert-butyl ((S)-3-(benzyloxy)-1-(((S)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroquinolin-3-yl)amino)-1-oxopropan-2-yl)carbamate

tert-butyl ((S)-3-(benzyloxy)-1-(((S)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroquinolin-3-yl)amino)-1-oxopropan-2-yl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2.1: potassium carbonate / acetone / 48 h / Reflux
3.1: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C
4.1: toluene / 24 h / Reflux
5.1: acetic acid; nitric acid / 1.5 h / 0 °C
5.2: 1.5 h / 80 °C
6.1: hydrazine hydrate / ethanol / 40 h / Reflux
7.1: dimethyl sulfide borane / tetrahydrofuran / 30 h / Reflux
8.1: benzyl chloroformate; 4-methyl-morpholine / dichloromethane / 6 h / -78 - 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

N-(tert-butoxycarbonyl)-3,4-(dihydroxy)-L-phenylalanine ethyl ester
1313214-06-0

N-(tert-butoxycarbonyl)-3,4-(dihydroxy)-L-phenylalanine ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 16h;

37178-37-3Relevant articles and documents

An alternative approach to the synthesis of the three fragments of anachelin H

Gamba-Sánchez, Diego,Garzón-Posse, Fabián,Prunet, Jo?lle

, p. 2702 - 2715 (2020/04/17)

The synthesis of the fully protected peptide, polyketide and alkaloid fragments of anachelin H is presented. The peptide fragment was prepared using a liquid phase peptide synthesis; the polyketide fragment was synthetized using a cross metathesis and an intramolecular oxa-Michael reaction as the key steps to introduce the desired stereochemistry; finally, the alkaloid fragment was obtained by an oxidative cyclization of a catechol derivative using potassium ferricyanide. The synthesis of all fragments was based on the use of natural amino acids as sources of asymmetry. The independent synthesis of the three fragments should allow more efficient biological studies on the fragments instead of the whole natural product. Experiments to illustrate the coupling of fragments and the effectiveness of the convergent strategy are also described.

NO-CARRIER-ADDED NUCLEOPHILIC [F-18] FLUORINATION OF AROMATIC COMPOUNDS

-

Page/Page column 18, (2010/11/03)

Phenyliodonium ylide derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are shown for use as precursors in aromatic nucleophilic substitution reactions. The iodonium ylide group is substituted by nucleophiles such as halide ions to provide the corresponding haloaryl derivatives. No- carrier-added [F-18]fluoride ion exclusively substitutes the iodonium ylide moiety in these derivatives and provides high specific activity F- 18 labeled fluoro derivatives. Protected L-dopa-6-iodonium ylide derivative have been synthesized as a precursors for the preparation of no-carrier-added 6-[F- 18]fluoro-L-dopa. The iodonium ylide group in this L-dopa.derivative is nucleophilically substituted by no-carrier-added [F-18]fluoride ion to provide a [F-18]fluoro intermediates which upon acid hydrolysis yielded 6-[F- 18]fluoro-L-dopa.

L-DOPA ethyl ester to treat Parkinson's disease

-

, (2008/06/13)

Patients suffering from Parkinson's disease are treated by administering a composition which contains an active ingredient and a pharmaceutically acceptable carrier. The active ingredient comprises L-DOPA ethyl ester in an amount which is at least 97% by weight of the active ingredient and L-DOPA in an amount which is less than 1% by weight of the active ingredient.

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