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Basic Information
| CAS No.: | 60-18-4 |
|---|---|
| Name: | L-Tyrosine |
| Molecular Structure: | |
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| Formula: | C9H11NO3 |
| Molecular Weight: | 181.191 |
| Synonyms: | (-)-alpha-Amino-p-hydroxyhydrocinnamic acid;Benzenepropanoic acid, alpha-amino-4-hydroxy-, (S)-;beta-(p-Hydroxyphenyl)alanine;4-Hydroxy-L-phenylalanine;Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-(S)-;alpha-Amino-beta-(4-hydroxyphenyl)propionic acid;Benzenepropanoic acid, .alpha.-amino-4-hydroxy-, (S)-;Tyrosine (USP);2-Amino-3-(4-hydroxyphenyl)propanoic acid-(S)-;Tyrosinum [Latin];L-2-Amino-3-p-hydroxyphenylpropanoic acid;Tirosina [Spanish];Tyrosine, L-;alpha-Amino-p-hydroxyhydrocinnamic acid, (-)-;Tyrosine, L- (8CI);2-Amino-3-(p-hydroxyphenyl)propionic acid;L-Tyrosine (JAN);3-(p-Hydroxyphenyl)alanine;2-Amino-3-(4-hydroxyphenyl)propanoic acid, (S)-;(2S)-2-azaniumyl-3-(4-hydroxyphenyl)propanoate;(S)-2-Amino-3-(p-hydroxyphenyl)propionic acid;(S)-3-(p-Hydroxyphenyl)alanine;(S)-alpha-Amino-4-hydroxybenzenepropanoic acid;Tyrosine [USAN:INN];Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)-;L-Tyrosine (9CI);(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid;3-(4-Hydroxyphenyl)-L-alanine;H-Tyr-OH; |
| EINECS: | 200-460-4 |
| Density: | 1.334 g/cm3 |
| Melting Point: | >300 °C (dec.)(lit.) |
| Boiling Point: | 385.163 °C at 760 mmHg |
| Flash Point: | 186.74 °C |
| Solubility: | 0.45 g/L (25 °C) in water |
| Appearance: | White to off-white powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38-40 |
| Safety: | 26-36-37/39-22 |
| PSA: | 83.55000 |
| LogP: | 1.04690 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; | 100% |
| With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.; | 100% |
| With dimethylsulfide; hydrogen fluoride at 0℃; for 2h; Product distribution; Var.: HF in anisole; | 99.5% |
Conditions
| Conditions | Yield |
|---|---|
| With ammonium bicarbonate; water In dichloromethane for 15h; α-chymotrypsin; | 100% |
| at 25℃; for 0.833333h; enzyme alcalase from Bacillus licheniforms; pH 8.2; | |
| With water at 37℃; Rate constant; pH 7.4; apparent rate constant of product formation; calculated nasal absorption rate constant; | |
| With water; sodium chloride In dimethyl sulfoxide at 37℃; Rate constant; also human plasma as reagent; | |
| Multi-step reaction with 4 steps 1: dichloromethane / 20 °C 2: copper diacetate; oxygen / acetonitrile / 20 h 3: potassium hydroxide / methanol; water / 7 h / Reflux 4: dimethyl sulfoxide; aq. phosphate buffer / 24 h / 37 °C / pH 7.4 View Scheme |
Conditions
| Conditions | Yield |
|---|---|
| With ammonium bicarbonate; water In dichloromethane for 12h; α-chymotrypsin; | 100% |
| With water at 37℃; Rate constant; pH 7.4; apparent rate constant of product formation; calculated nasal absorption rate constant; | |
| With water; sodium chloride In dimethyl sulfoxide at 37℃; Rate constant; also human plasma as reagent; |
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N,O-bis-allyloxycarbonyl-L-tyrosine
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L-tyrosine
Conditions
| Conditions | Yield |
|---|---|
| With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; acetic acid In dichloromethane Product distribution; slectivity of cleavge of allyl and allyloxycarbonyl groups; other amino acid derivatives; | 100% |
| With tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride In dichloromethane Ambient temperature; | 95% |
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N-tert-butoxycarbonyl-O-2,6-dichlorobenzyl-L-tyrosine
- 60-18-4
L-tyrosine
Conditions
| Conditions | Yield |
|---|---|
| With Nafion H; dimethylsulfide; 3-methyl-phenol; trifluoroacetic acid for 3h; | 100% |
| With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; | 100% |
| With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.; | 100% |
Conditions
| Conditions | Yield |
|---|---|
| With water at 170℃; for 0.05h; Microwave irradiation; | 100% |
| With sodium tetrahydroborate In methanol; aq. phosphate buffer at 20℃; for 1h; Cooling with ice; Sealed tube; | 87% |
| Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 72 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 24 h / 20 °C 3: acetonitrile / 2.6 h / pH 7.2 / Photolysis; HEPES buffer View Scheme |
Conditions
| Conditions | Yield |
|---|---|
| With formate dehydrogenase; NAD; ammonium formate at 30℃; for 24h; PheDH; | 99% |
| With L-phenylalanine; L-specific transaminase ywfG at 20℃; for 16h; pH=8; aq. potassium phosphate buffer; Enzymatic reaction; |
Conditions
| Conditions | Yield |
|---|---|
| With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; formate dehydrogenase; phenylalanine dehydrogenase In water at 30℃; for 24h; | 99% |
| With L-glutamic acid; pyridoxal 5'-phosphate In water at 40℃; for 4h; E.coli Aspartate transaminase, pH 8; | 80% |
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(RS)-tyrosinamide hydrochloride
- 60-18-4
L-tyrosine
Conditions
| Conditions | Yield |
|---|---|
| With pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride In aq. buffer at 40℃; for 6h; pH=7.0; Enzymatic reaction; | 99% |
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(Z)-2-benzamido-3-(p-hydroxyphenyl)-2-propenic acid
- 60-18-4
L-tyrosine
Conditions
| Conditions | Yield |
|---|---|
| With hydrogen; PF6 In tetrahydrofuran at 25℃; under 760 Torr; | 98% |
| With hydrogen; PF6 In tetrahydrofuran at 25℃; under 760 Torr; effects of solvents dependency of the optical yields; |
Raw Materials
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L-Tyrosine
Specification
1. Introduction of L-Tyrosine
L-Tyrosine, with the IUPAC Name of (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid, is one kind of white to off-white powder. For being stable in normal condition, it is incompatible with strong oxidizing agents, strong reducing agents. And it belongs to the Product Categories which include Food and Feed Additive;Tyrosine [Tyr, Y];Amino Acids;Amino Acids and Derivatives;alpha-Amino Acids;Biochemistry;Nutritional Supplements;L-Amino Acids;Amino Acids.
2. Properties of L-Tyrosine
L-Tyrosine has the following property datas: (1)Index of Refraction: 1.614; (2)Molar Refractivity: 47.37 cm3; (3)Molar Volume: 135.8 cm3; (4)Polarizability: 18.78×10-24cm3; (5)Surface Tension: 65.7 dyne/cm; (6)Density: 1.333 g/cm3; (7)Flash Point: 186.7 °C; (8)Enthalpy of Vaporization: 66.87 kJ/mol; (9)Melting Point: >300 °C (dec.)(lit.); (10)Boiling Point: 385.2 °C at 760 mmHg; (11)Vapour Pressure: 1.27E-06 mmHg at 25°C; (12)Water Solubility: 0.45 g/L (25 oC).
3. Structure Descriptors of L-Tyrosine
You could convert the following datas into the molecular structure:
(1).InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1
(2).InChIKey: InChIKey=OUYCCCASQSFEME-QMMMGPOBSA-N
(3).Smiles: C([C@H](Cc1ccc(O)cc1)N)(O)=O
4. Toxicity of L-Tyrosine
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | > 1450mg/kg (1450mg/kg) | Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 1117, 1977. |
5. Safety Information of L-Tyrosine
Hazard Codes:
Xi Risk Statements: 36/37/38-40
R36/37/38: Irritating to eyes, respiratory system and skin.
R40: Limited evidence of a carcinogenic effect.
Safety Statements: 26-36-37/39-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S37/39: Wear suitable gloves and eye/face protection.
S22: Do not breathe dust.
WGK Germany: 3
RTECS: YP2275600
HS Code: 29225000
6. Use and Preparation of L-Tyrosine
L-Tyrosine appears to be a successful addition to conventional treatment for COCAINE abuse and withdrawal. It may be used in conjunction with other amino acids such as tryptophan. It can be used as biochemical reagents. It is used for the treatment of THYROID hyperTHYROIDism. It can also be used as a nutrition agent for old and children.
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