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L-alpha-Methyltyrosine

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Name

L-alpha-Methyltyrosine

EINECS 211-599-5
CAS No. 672-87-7 Density 1.283g/cm3
PSA 83.55000 LogP 1.43700
Solubility N/A Melting Point 320-340°C dec.
Formula C10H13 N O3 Boiling Point 383.7oC at 760 mmHg
Molecular Weight 195.218 Flash Point 185.9oC
Transport Information N/A Appearance White Solid
Safety 2368400 Risk Codes 2368400
Molecular Structure Molecular Structure of 672-87-7 (ALPHA-METHYL-L-P-TYROSINE) Hazard Symbols N/A
Synonyms

Tyrosine,a-methyl-, L- (8CI);(S)-2-(4-Hydroxybenzyl)-2-aminopropanoic acid; (S)-a-Methyltyrosine; Demser; L(-)-Metyrosine;L-Metyrosine; L-a-MT;L-a-Methyl-p-tyrosine; L-a-Methyltyrosine; MK 781;Metirosine; Metyrosine; a-Methyl-L-tyrosine

Article Data 7

L-alpha-Methyltyrosine Synthetic route

1299492-19-5

(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrogen bromide salt

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With water; hydrogen bromide at 105℃; for 17h; Product distribution / selectivity;86%
1299492-09-3

2-(S)-amino-3-(4-methoxyphenyl)-2-methylpropionamide

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With water; hydrogen bromide at 120℃; for 5h; Product distribution / selectivity;84%
Multi-step reaction with 2 steps
1: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr
2: water; hydrogen bromide / 17 h / 105 °C
View Scheme
1299492-14-0

(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrochloride

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogen bromide In water at 120℃; for 4h; Product distribution / selectivity;83%
1299492-20-8

(2S)-2-amino-3-(4-methoxyphenyl)-2-methylpropionamide formic acid salt

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With water; hydrogen bromide at 105℃; for 17h; Product distribution / selectivity;82%

(S)-N2-benzoyl-O4',2-dimethyltyrosine

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 4h;75.4%

tert-butyl (2R)-2-amino-3-(4-methoxyphenyl)-2-methylpropanoate

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Stage #1: tert-butyl (2R)-2-amino-3-(4-methoxyphenyl)-2-methylpropanoate With boron tribromide In dichloromethane at 20℃; for 1.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity;
45.4%
121703-96-6

N-Chloroacetyl-α-methyltyrosine

A

672-87-7

L-methyltyrosine

B

672-86-6

α-methyl-D-tyrosine

C

121704-37-8

N-Chloroacetyl-D-α-methyltyrosine

D

121703-96-6, 121704-37-8

N-Chloroacetyl-L-α-methyltyrosine

Conditions
ConditionsYield
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yields of byproduct given;A 30%
B n/a
C n/a
D n/a
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yields of byproduct given;A n/a
B 30%
C n/a
D n/a
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yield given. Yields of byproduct given;
65555-88-6

α-methyl-β-p-methoxyphenyl-alanine

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogen bromide
121703-96-6

N-Chloroacetyl-α-methyltyrosine

A

672-87-7

L-methyltyrosine

B

121704-37-8

N-Chloroacetyl-D-α-methyltyrosine

Conditions
ConditionsYield
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2;
16109-65-2

2-Nitro-2-(4-hydroxybenzyl)propionsaeureethylester

672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide; nickel 1.) MeOH, reflux, 1 h, 2.) MeOH, 28 h; Yield given. Multistep reaction;

L-alpha-Methyltyrosine Chemical Properties

 Molecule structure of L-Tyrosine, a-methyl- (CAS NO.672-87-7):

IUPAC Name: (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
Molecular Weight: 195.21512 [g/mol]
Molecular Formula: C10H13NO3 
Index of Refraction: 1.599
Molar Refractivity: 52.01 cm3
Molar Volume: 152 cm3
Surface Tension: 60.6 dyne/cm
Density: 1.283 g/cm3 
Melting Point: 320-340 °C
Storage temp.: −20 °C
Flash Point: 185.9 °C
Enthalpy of Vaporization: 66.7 kJ/mol
Boiling Point: 383.7 °C at 760 mmHg
Vapour Pressure: 1.42E-06 mmHg at 25 °C
XLogP3-AA: -1.6
H-Bond Donor: 3
H-Bond Acceptor: 4
Rotatable Bond Count: 3
Tautomer Count: 2
Exact Mass: 195.089543
MonoIsotopic Mass: 195.089543
Topological Polar Surface Area: 83.6
Heavy Atom Count: 14
Canonical SMILES: CC(CC1=CC=C(C=C1)O)(C(=O)O)N
Isomeric SMILES: C[C@](CC1=CC=C(C=C1)O)(C(=O)O)N
InChI: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
InChIKey: NHTGHBARYWONDQ-JTQLQIEISA-N
EINECS: 211-599-5
Product Categories of L-Tyrosine, a-methyl- (CAS NO.672-87-7): Amino acids methyl、ethyl、t-butyl series;Amino Acids & Derivatives

L-alpha-Methyltyrosine Uses

 L-Tyrosine, a-methyl- (CAS NO.672-87-7) is a tyrosine hydroxylase inhibitor. It is also an antihypertensive in pheochromocytoma.

L-alpha-Methyltyrosine Safety Profile

Safety Statements: 22-24/25
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

L-alpha-Methyltyrosine Specification

 L-Tyrosine, a-methyl- (CAS NO.672-87-7) is also called Alpha-Methyltyrosine ; Metyrosine [USAN] ;
(-)-(S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure ; (-)-alpha-Methyl-L-tyrosine (S)-alpha-Methyltyrosine ; Demser ; L-alpha-Methyltyrosine ; Metirosina ; Metirosina [INN-Spanish] ; Metirosinum ; Metirosinum [INN-Latin] ; Metyrosine ; L-Tyrosine, alpha-methyl-, (-)- ; Metirosine . It is white Solid. 

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