Product Name

  • Name

    2-METHYL-3-(3,4-DIHYDROXYPHENYL)-DL-ALANINE

  • EINECS
  • CAS No. 55-40-3
  • Article Data20
  • CAS DataBase
  • Density 1.403g/cm3
  • Solubility
  • Melting Point 300-301 °C (decomp)
  • Formula C10H13 N O4
  • Boiling Point 441.6°Cat760mmHg
  • Molecular Weight 211.218
  • Flash Point 220.9°C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes R36
  • Molecular Structure Molecular Structure of 55-40-3 (2-METHYL-3-(3,4-DIHYDROXYPHENYL)-DL-ALANINE)
  • Hazard Symbols Xi
  • Synonyms Alanine,3-(3,4-dihydroxyphenyl)-2-methyl- (6CI,8CI); (?à)-Methyldopa; (?à)-a-Methyldopa; 2-(3,4-Dihydroxybenzyl)-2-aminopropanoic acid;DL-2-Methyl-3-(3,4-dihydroxyphenyl)alanine; DL-Methyldopa; DL-a-Methyl DOPA; DL-a-Methyl-3-(3,4-dihydroxyphenyl)alanine;Metholes; Mulfasin; Racemic a-methyldopa
  • PSA 103.78000
  • LogP 1.14260

Synthetic route

DL-N-Acetyl-α-methyl-β-<3,4-dimethoxy-phenyl>-alanin
5934-66-7

DL-N-Acetyl-α-methyl-β-<3,4-dimethoxy-phenyl>-alanin

alpha-methyldopa
55-40-3

alpha-methyldopa

Conditions
ConditionsYield
(hydrolysis);
2-Amino-3-(3,4-bis-benzyloxy-phenyl)-2-methyl-propionic acid ethyl ester; hydrochloride
84713-76-8

2-Amino-3-(3,4-bis-benzyloxy-phenyl)-2-methyl-propionic acid ethyl ester; hydrochloride

alpha-methyldopa
55-40-3

alpha-methyldopa

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal 1.) ethanol; Yield given. Multistep reaction;
(+-)-2-amino-3-<3.4-dimethoxy-phenyl>-2-methyl-propionic acid

(+-)-2-amino-3-<3.4-dimethoxy-phenyl>-2-methyl-propionic acid

alpha-methyldopa
55-40-3

alpha-methyldopa

Conditions
ConditionsYield
With hydrogen bromide
(+-)-2-amino-3-<3-hydroxy-4-methoxy-phenyl>-2-methyl-propionic acid

(+-)-2-amino-3-<3-hydroxy-4-methoxy-phenyl>-2-methyl-propionic acid

alpha-methyldopa
55-40-3

alpha-methyldopa

Conditions
ConditionsYield
With hydrogenchloride
L-Dopa ethyl ester hydrochloride
23234-41-5

L-Dopa ethyl ester hydrochloride

alpha-methyldopa
55-40-3

alpha-methyldopa

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2.) K2CO3 / 2.) Acetone
2: 1.) solid KOH 2.) 1N HCl / 1.) tetrabutylammonium iodide / 1.) acetonitrile, 0 to 15 deg C 2.) ether, 0 deg C.
3: 1.) hydrogen 2.) 6N HCl / 1.) 10 percent Pd/C / 1.) ethanol
View Scheme
3-(3,4-Bis-benzyloxy-phenyl)-2-{[1-(2,4,6-trimethyl-phenyl)-meth-(Z)-ylidene]-amino}-propionic acid ethyl ester
84713-73-5

3-(3,4-Bis-benzyloxy-phenyl)-2-{[1-(2,4,6-trimethyl-phenyl)-meth-(Z)-ylidene]-amino}-propionic acid ethyl ester

alpha-methyldopa
55-40-3

alpha-methyldopa

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) solid KOH 2.) 1N HCl / 1.) tetrabutylammonium iodide / 1.) acetonitrile, 0 to 15 deg C 2.) ether, 0 deg C.
2: 1.) hydrogen 2.) 6N HCl / 1.) 10 percent Pd/C / 1.) ethanol
View Scheme
(±)-3-(3,4-dimethoxyphenyl)-2-amino-2-methylpropanenitrile
2543-46-6

(±)-3-(3,4-dimethoxyphenyl)-2-amino-2-methylpropanenitrile

alpha-methyldopa
55-40-3

alpha-methyldopa

Conditions
ConditionsYield
With water; hydrogen bromide
1-Fluoro-2-isocyanato-benzene
16744-98-2

1-Fluoro-2-isocyanato-benzene

alpha-methyldopa
55-40-3

alpha-methyldopa

3-(3,4-dihydroxyphenyl)-2-(3-(2-fluorophenyl)ureido)-2-methylpropanoic acid

3-(3,4-dihydroxyphenyl)-2-(3-(2-fluorophenyl)ureido)-2-methylpropanoic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 40 - 50℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent;90%
alpha-methyldopa
55-40-3

alpha-methyldopa

4-bromophenyl isocyanate
2493-02-9

4-bromophenyl isocyanate

(3-(4-bromophenyl)ureido)-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

(3-(4-bromophenyl)ureido)-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 40 - 50℃; for 3h;90%
alpha-methyldopa
55-40-3

alpha-methyldopa

o-trifluoromethyl-phenylisocyanate
2285-12-3

o-trifluoromethyl-phenylisocyanate

3-(3,4-dihydroxyphenyl)-2-methyl-2-(3-(2-(trifluoromethyl)phenyl)ureido)propanoic acid

3-(3,4-dihydroxyphenyl)-2-methyl-2-(3-(2-(trifluoromethyl)phenyl)ureido)propanoic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 40 - 50℃; for 3h;90%
alpha-methyldopa
55-40-3

alpha-methyldopa

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

2-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

2-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 40 - 50℃; for 3h;90%
alpha-methyldopa
55-40-3

alpha-methyldopa

m-chlorophenyl isocyanate
2909-38-8

m-chlorophenyl isocyanate

2-(3-(3-chlorophenyl)ureido)-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

2-(3-(3-chlorophenyl)ureido)-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 40 - 50℃; for 3h;90%
cis-dichlorobis(triphenylphosphine)platinum(II)
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

alpha-methyldopa
55-40-3

alpha-methyldopa

Pt(P(C6H5)3)2(O2C6H3CH2CCH3(NH2)COOH)*0.5CH2Cl2

Pt(P(C6H5)3)2(O2C6H3CH2CCH3(NH2)COOH)*0.5CH2Cl2

Conditions
ConditionsYield
With potassium hydroxide; dichloromethane In methanol; benzene to a suspn. of substituted catechol in benzene was added MeOH soln. of KOH; prepd. soln. was syringed into suspn. of Pt complex in benzene; stirring at room temp. for 3.5 h (Ar); filtration, evapn., washing with water, drying in vac., dissoln. in CH2Cl2, filtration, evapn., washing with ether, drying in vac.; elem. anal.;84%
alpha-methyldopa
55-40-3

alpha-methyldopa

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-Chloroacetyl-α-methyl-DOPA
121704-32-3

N-Chloroacetyl-α-methyl-DOPA

Conditions
ConditionsYield
In acetonitrile for 1.5h; Heating;60%
1-chloroethyl pivalate
40258-80-8

1-chloroethyl pivalate

alpha-methyldopa
55-40-3

alpha-methyldopa

A

α-methyldopa pivaloylethyl ester
81660-38-0

α-methyldopa pivaloylethyl ester

B

3-(3,4-Dihydroxy-phenyl)-2-[1-(2,2-dimethyl-propionyloxy)-ethylamino]-2-methyl-propionic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester
102108-09-8

3-(3,4-Dihydroxy-phenyl)-2-[1-(2,2-dimethyl-propionyloxy)-ethylamino]-2-methyl-propionic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester

Conditions
ConditionsYield
With 4 A molecular sieve In various solvent(s) at 75℃; for 8h; Product distribution; other temperature, various solvents; other alkylating agents; other amino acids; with or without LiBr;
...Expand
alpha-methyldopa
55-40-3

alpha-methyldopa

2-Amino-3-(3,4-dioxo-cyclohexa-1,5-dienyl)-2-methyl-propionic acid
73688-25-2

2-Amino-3-(3,4-dioxo-cyclohexa-1,5-dienyl)-2-methyl-propionic acid

Conditions
ConditionsYield
With phenoloxidase from Lucilia cuprina pupae Enzyme kinetics; Oxidation;
With oxygen In phosphate buffer at 20℃; pH=6.8; Enzyme kinetics; Further Variations:; Reagents;
alpha-methyldopa
55-40-3

alpha-methyldopa

α-methyldopachrome
131923-54-1

α-methyldopachrome

Conditions
ConditionsYield
With sodium periodate In phosphate buffer for 0.166667h; pH=6.0; Oxidation; cyclization;
4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one
83-07-8

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one

alpha-methyldopa
55-40-3

alpha-methyldopa

potassium hexacyanoferrate(III)

potassium hexacyanoferrate(III)

[Fe(HOC6H2(O)(CH2C(CH3)(NH2)COOH)NHCC(O)N(C6H5)N(CH3)C(CH3))2(CN)(H2O)]
753453-85-9

[Fe(HOC6H2(O)(CH2C(CH3)(NH2)COOH)NHCC(O)N(C6H5)N(CH3)C(CH3))2(CN)(H2O)]

Conditions
ConditionsYield
In water hot aq. soln. of catecholamine was mixed with hot aq. soln. of 4-aminoantipyrine (60°C); mixt. was mixed with stirring with hot soln. of Fe compd. (60°C); mixt. was kept at room temp. for 6 h; filtered; washed (H2O, pentane); collected; dried in vac. over CaCl2; elem. anal.;
...Expand
4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one
83-07-8

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one

alpha-methyldopa
55-40-3

alpha-methyldopa

copper(II) sulfate
7758-99-8

copper(II) sulfate

[Cu(O2C6H2(CH2C(CH3)(NH2)COOH)NHCC(O)N(C6H5)N(CH3)C(CH3))(H2O)2]*4H2O

[Cu(O2C6H2(CH2C(CH3)(NH2)COOH)NHCC(O)N(C6H5)N(CH3)C(CH3))(H2O)2]*4H2O

Conditions
ConditionsYield
With ammonia In water ammonia soln. was added dropwise with stirring to soln. of Cu salt; hot (60°C) aq. soln. of catecholamine and hot (60°C) aq. soln.of 4-aminoantipyrine were added with stirring; concd.; kept in cupboard; filtered; washed (H2O, pentane); collected; dried in vac. over CaCl2; elem. anal.;
...Expand
alpha-methyldopa
55-40-3

alpha-methyldopa

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

C28H28N2O8

C28H28N2O8

Conditions
ConditionsYield
Stage #1: alpha-methyldopa With potassium hydroxide In methanol; ethanol for 1h;
Stage #2: o-phthalic dicarboxaldehyde In methanol; ethanol for 2h;
alpha-methyldopa
55-40-3

alpha-methyldopa

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

C28H30CrN2O10*H2O

C28H30CrN2O10*H2O

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium hydroxide / methanol; ethanol / 1 h
1.2: 2 h
2.1: methanol / 2 h / Reflux
View Scheme
manganese(II) chloride hydrate

manganese(II) chloride hydrate

alpha-methyldopa
55-40-3

alpha-methyldopa

aspirin
50-78-2

aspirin

C19H23MnNO10

C19H23MnNO10

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;
...Expand
iron(II) chloride hydrate

iron(II) chloride hydrate

alpha-methyldopa
55-40-3

alpha-methyldopa

aspirin
50-78-2

aspirin

C19H23FeNO10

C19H23FeNO10

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;
...Expand
cobalt(II) chloride hydrate

cobalt(II) chloride hydrate

alpha-methyldopa
55-40-3

alpha-methyldopa

aspirin
50-78-2

aspirin

C19H23CoNO10

C19H23CoNO10

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;
...Expand
nickel(II) dichloride hydrate

nickel(II) dichloride hydrate

alpha-methyldopa
55-40-3

alpha-methyldopa

aspirin
50-78-2

aspirin

C19H23NNiO10

C19H23NNiO10

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;
...Expand
copper(II) chloride hydrate

copper(II) chloride hydrate

alpha-methyldopa
55-40-3

alpha-methyldopa

aspirin
50-78-2

aspirin

C19H23CuNO10

C19H23CuNO10

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;
...Expand
manganese(II) chloride hydrate

manganese(II) chloride hydrate

4-acetaminophenol
103-90-2

4-acetaminophenol

alpha-methyldopa
55-40-3

alpha-methyldopa

C18H24MnN2O8

C18H24MnN2O8

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;
...Expand
iron(II) chloride hydrate

iron(II) chloride hydrate

4-acetaminophenol
103-90-2

4-acetaminophenol

alpha-methyldopa
55-40-3

alpha-methyldopa

C18H24FeN2O8

C18H24FeN2O8

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;
...Expand

3-Hydroxy-alpha-methyltyrosine Chemical Properties

IUPAC  Name: 2-Amino-3-(3,4-dihydroxyphenyl)butanoic acid      
Empirical Formula: C10H13NO4
Molecular Weight: 211.2145 
Freely Rotating Bonds: 6
Polar Surface Area: 48 Å2
Index of Refraction: 1.629
Molar Refractivity: 53.89 cm3
Molar Volume: 151.5 cm3
Polarizability: 21.36× 10-24 cm3
Surface Tension: 71.2 dyne/cm
Density: 1.393 g/cm3
Flash Point: 216.2 °C
Enthalpy of Vaporization: 72.72 kJ/mol
Boiling Point: 433.9 °C at 760 mmHg
Vapour Pressure: 2.69E-08 mmHg at 25°C 
The Cas Register Number of  3-Hydroxy-alpha-methyltyrosine is 55-40-3.The chemical synonyms of  3-Hydroxy-alpha-methyltyrosine (CAS NO.55-40-3) are 2-Amino-3-(3,4-dihydroxyphenyl)butanoic acid .The molecular structure of  3-Hydroxy-alpha-methyltyrosine (CAS NO.55-40-3) is
.

3-Hydroxy-alpha-methyltyrosine Uses

  3-Hydroxy-alpha-methyltyrosine (CAS NO.55-40-3) is used in organic synthesis.

3-Hydroxy-alpha-methyltyrosine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36 
R36: Irritating to eyes.
Safety Statements: 26-36/37 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37: Wear suitable protective clothing and gloves.
WGK Germany: 3

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