Tyrosine

CAS Number 60-18-4
Molecular Formula C9H11NO3
Molecular Weight 181.191 g/mol
InChI Key OUYCCCASQSFEME-QMMMGPOBSA-N
LogP -2.3
Synonyms
  • L-tyrosine
  • tyrosine
  • 60-18-4
  • (S)-Tyrosine
  • p-Tyrosine
  • H-Tyr-OH
  • L-p-Tyrosine
  • (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
  • 4-Hydroxy-L-phenylalanine
  • L-(-)-Tyrosine
  • Tyrosine, L-
  • Tyrosinum [Latin]
  • Tyrosine (VAN)
  • Tirosina [Spanish]
  • (-)-alpha-Amino-p-hydroxyhydrocinnamic acid
  • (S)-alpha-Amino-4-hydroxybenzenepropanoic acid
  • 3-(4-Hydroxyphenyl)-L-alanine
  • L-Phenylalanine, 4-hydroxy-
  • beta-(p-Hydroxyphenyl)alanine
  • Tyrosinum
  • (S)-3-(p-Hydroxyphenyl)alanine
  • L-Tyrosin
  • (S)-(-)-Tyrosine
  • Tyrosine [USAN:INN]
  • L-2-Amino-3-p-hydroxyphenylpropanoic acid
  • FEMA No. 3736
  • Rxosine
  • L-Tyrosine, homopolymer
  • Tyrosine Power
  • (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid
  • HSDB 2003
  • alpha-Amino-beta-(4-hydroxyphenyl)propionic acid
  • AI3-09055
  • tirosina
  • Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)-
  • NSC 82624
  • alpha-Amino-p-hydroxyhydrocinnamic acid, (-)-
  • L-Tyr
  • (S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid
  • (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid
  • L-Tyrosine, monomer
  • tyr
  • alpha-Amino-4-hydroxybenzenepropanoic acid, (S)-
  • Free-Form L-Tyrosine
  • UNII-42HK56048U
  • L-Tyrosine (9CI)
  • Benzenepropanoic acid, alpha-amino-4-hydroxy-, (S)-
  • Tyrosine (USP/INN)
  • 4ts1
  • EINECS 200-460-4
  • beta-p-Hydroxyphenylalanine
  • 2-Amino-3-(4-hydroxyphenyl)propanoic acid, (S)-
  • CHEBI:17895
  • OUYCCCASQSFEME-QMMMGPOBSA-N
  • 3-(p-Hydroxyphenyl)alanine
  • MFCD00002606
  • 55520-40-6
  • NCGC00159350-02
  • Tyrosine (L-Tyrosine)
  • DSSTox_CID_3730
  • Melanin synthesized from Tyr substrate catalyzed by tyrosinase for 6 hrs
  • L-2-Amino-3-(4-hydroxyphenyl)propionic acid
  • DSSTox_RID_77170
  • DSSTox_GSID_23730
  • 2-Amino-3-(p-hydroxyphenyl)propionic acid
  • DD69927C-C6A8-4BC6-8E9A-0AB423B176E7
  • CAS-60-18-4
  • Melanin synthesized from Tyr substrate catalyzed by tyrosinase for 6 hrs, oxidized with hydrogen peroxide
  • Melanin synthesized from Tyr substrate catalyzed by tyrosinase for 6 hrs, oxidized with hydrogen peroxide, <3 kd fraction
  • Melanin synthesized from Tyr substrate catalyzed by tyrosinase, brominated with N-bromosuccinimide
  • Melanin synthesized from Tyr substrate catalyzed by tyrosinase, sulfonated using sulfur trioxide/DMF complex for 1.5-7 hours
  • DTY
  • Benzenepropanoate
  • 2csm
  • (L)-Tyrosine
  • (-) tyrosine
  • H-Tyr
  • L-Tyrosine (JAN)
  • (-)-.alpha.-Amino-p-hydroxyhydrocinnamic acid
  • L-Tyrosine;H-Tyr-OH

Applications:


Complex Mixture of Acids, Bases, Amino Acids, and Neutral Compounds



Primesep 100 separates a mixture of amino acids (tyrosine, phenylalanine), organic acids (benzoic acid, mandelic acid), amines (benzylamine, pyridine), and neutrals (benzonitrile, toluene) in one HPLC run by combining reversed-phase, cation-exchange, and polar interactions. The method is tunable and peak order can be changed significantly by adjusting acetonitrile and trifluoroacetic acid concentrations. The separation method uses a mobile phase mixture of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) and compatible with UV, mass spec (LC/MS) and evaporative light scattering (ELSD) detection.



Application Analytes:

Amino Acids
Benzoic Acid
Benzonitrile
Benzylamine
Mandelic Acid
Organic Acids
Phenylalanine
Pyridine
Toluene
Tyrosine

HPLC Analysis of the Catecholamine Pathway
Primesep 200 separates catecholamines in the catecholamine pathway in 10 minutes. Phenylalanine, tyrosine, DOPA, dopamine, norepinephrine, and epinephrine are baseline resolved by a combination of reversed-phase, ion-exchange, and ion-exclusion mechanisms. Excellent peak shape results with a mass spec compatible mobile phase of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) with UV detection at 210 nm.

Condition

Column Primesep 200, 3.2x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer TFA
Flow Rate 0.5 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds Tyrosine, DOPA, Phenylalanine, Norepinephrine, Epinephrine, Dopamine
 

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Dopamine
Epinephrine
Phenylalanine
Tyrosine

Bufferless Ion Separation (BLIS™) Chromatography of Amino Acids (1)

Amino acids are the building blocks of proteins and are widely used as supplements.  Amino acids can exist in acidic, basic or zwitterionic form depending on the pH of their environment (mobile phase in this case).  Primesep 200 is a reverse-phase column with embedded weak acidic ion-pairing groups which allows for retention and separation of amino acids without requiring a buffer making it ideal for use with UV detection, mass spectrometry (MS), evaporative light scattering detection (ELSD).

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Phenylalanine
Tyrosine

HPLC Analysis of Polar Basic and Acetic Compounds on Primesep AB Column
Mixture of polar acidic and basic compounds is separated on a Primesep AB mixed-mode HPLC column. Dopamine and tyrosine are retained by combination of reversed-phase and cation-exchange mechanisms. Maleic acid is retained by anion-exchange mechanism, and benzoic acid is retained by reversed-phase mechanism. Primesep AB is a trimodal column with a C12 hydrophobic chain and cation-exchange and anion exchange groups on the surface. Method utilizes UV detection but can be used with other detection techniques (ELSD, LC/MS, Corona).

Condition

Column Primesep AB, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer TFA - 0.1%
Flow Rate 1.0 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Monocarboxylic acid,  Hydrophilic, Ionizable, Hormone
Analyzing Compounds Tyrosine, Dopamine, Maleic Acid, Benzoic Acid
 

Application Analytes:

Benzoic Acid
Dopamine
Maleic Acid
Tyrosine

HPLC Separation of Compounds of Catecholamine Pathway
The catecholamine neurotransmitters are amino-acid derivatives of tyrosine. DOPA, tyrosine, phenylalanine, norepinephrine, epinephrine, and dopamine and baseline are resolved on a Primesep 200 column with UV-transparent phosphate buffer. This method can be used for the analysis of catecholamines and related impurities in various matrices. The peak order and retention time can be changed by changing the amount of ACN, buffer concentration and buffer pH. Various buffers can be used to accommodate the desired detection technique. Primesep 200 is a reversed-phase cation-exchange mixed-mode column that can be used for analysis of polar neutral, polar ionizable, polar zwitterionic, hydrophobic neutral, and hydrophobic ionic compounds in the same run. Column can be operated in reverse-phase, cation-exchange, anion-exclusion, HILIC and mixed-modes depending on the mobile phase selection and the nature of the analytes. The column is compatible with LC/MS and does not require the use of ion-pairing reagents.

Condition

Column Primesep 200, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer TFA, AmFm
Flow Rate 1.0 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds Tyrosine, DOPA, Phenylalanine, Norepinephrine, Epinephrine, Dopamine
 

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Dopamine
Epinephrine
Phenylalanine
Tyrosine

HPLC Separation of Catecholamines on Primesep 100 Column with Phosphate Buffers
chr_284.gif The catecholamine neurotransmitters are amino-acid derivatives of tyrosine. DOPA, tyrosine, phenylalanine, norepinephrine, epinephrine, and dopamine and baseline are resolved on a Primesep 100 column with UV-transparent phosphate buffer. This method can be used for analysis of catecholamines and related impurities in various matrices. Peak order and retention time can be changed by changing the amount of ACN, buffer concentration and buffer pH. Various buffers can be used to accommodate desired detection technique. Primesep 100 is a reversed-phase cation-exchange mixed-mode column that can be used for analysis of polar neutral, polar ionizable, polar zwitter-ionic, hydrophobic neutral, and hydrophobic ionic compounds in the same run. Column can be operated in reverse-phase, cation-exchange, anion-exclusion, HILIC and mixed-modes depending on the mobile phase selection and nature of analytes. Column is compatible with LC/MS and does not require use of ion-pairing reagents.

Condition

Column Primesep 100, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer Na2HPO4
Flow Rate 1.0 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds Tyrosine, DOPA, Phenylalanine, Norepinephrine, Epinephrine, Dopamine
 

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Dopamine
Epinephrine
Norepinephrine
Phenylalanine
Tyrosine

HPLC Separation of Amino Acids in Zero Organic Mode on Primesep 200 column
Essential and non-essential amino acids can be retained and separated in zero-organic mode on Primesep mixed-mode HPLC columns. Zero-organic mode is required to monitor isotopes of carbon. Amino acids are retained by combination of reversed-phase and cation-exchange mechanisms. At lower pH, some of the amino acids are more hydrophobic. Buffer pH will affect ionization state of amino acids, and at higher pH (above 2.5), the amino acids will be less hydrophobic and retentive in zero-organic mode. Amino acids can be monitored by low UV. Method can be used in archeological research for analysis of various molecules where presence of organic component of the mobile phase interferes with analysis.

Condition

Column Primesep 200, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer Na2HPO4
Flow Rate 1.0 ml/min
Detection UV 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements
Analyzing Compounds Valine, Leucyne, Isoleycine, Tyrosine, Phenylalanine, Histidine, Lysine
 

Application Analytes:

Histidine
Isoleucine
Leucine
Lysine
Phenylalanine
Tyrosine
Valine

HPLC Separation of Amino Acids in HILIC and Cation-Exchange Modes
chr_306.gif Amino acids can be retained and separated on a Primesep S2 column in HILIC/cation-exchange mode.

Condition

Column Primesep S2, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer AmFm
Flow Rate 1.0 ml/min
Detection UV, 270 nm
 

Description

Class of Compounds Drug, Acid, Monocarboxylic acid,  Hydrophilic, Ionizable, Hormone
Analyzing Compounds Dopa, Tyrosine, Phenylalanine
 

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Phenylalanine
Tyrosine

HPLC Separation of Lysine and Arginine from Other Amino Acids
  Application Notes: Amino acids are polar ionic compounds which are not retained on reversed-phase column without ion-pairing reagent. In our application, lysine and arginine can be separated from other amino acids. Amino acids with a pH between 3 and 5 and with one basic and one acidic group become very polar. Therefore these amino acids don’t have strong ion-exchange interaction with Primesep C stationary phase. Amino acids with two amino groups still carry positive net charge and can interact with stationary phase by cations-exchange mechanism. pH variation of the mobile phase can be an effective tool to adjust selectivity of separation for zwitter-ionic, basic and acidic compounds. This method can be used for separation of mono-charged compounds from compounds having an extra charge. Application Columns: Primesep C Application compounds: Aspartic acid, Glutamic acid, Aspargine, Glycine, Proline, Alanine, Phenylalanine, Tyrosine, Leucine, Lysine, Arginine Detection technique: UV, LC/MS, ELSD/CAD

Condition

Column Primesep C, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN - 15%
Buffer AmAc pH 5.0- 15 mM
Flow Rate 1.0 ml/min
Detection ELSD
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements
Analyzing Compounds Aspartic acid, Glutamic acid, Aspargine, Glycine, Proline, Alanine, Phenylalanine, Tyrosine, Leucine, Lysine, Arginine
 

Application Analytes:

Alanine
Arginine
Asparagine
Aspartic Acid
Glutamic Acid
Glycine
Leucine
Lysine
Phenylalanine
Proline
Tyrosine

HPLC Separation of Mixture of Conditionally Essential Amino Acids on Primesep 100 Column
 

Condition

Column Primesep 100, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 35/65%
Buffer H2SO4 0.05% 12 min hold, gradient 0.05-0.20, 13 min
Flow Rate 1.0 ml/min
Detection UV, 200 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid
Analyzing Compounds Amino acids
 

Application Analytes:

Amino Acids
Arginine
Cysteine
Glycine
L-Cysteine
L-Glutamine
Proline
Tyrosine