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Chemistry

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Also known as: L-tyrosine, 60-18-4, (s)-tyrosine, P-tyrosine, L-p-tyrosine, (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Molecular Formula
C9H11NO3
Molecular Weight
181.19  g/mol
InChI Key
OUYCCCASQSFEME-QMMMGPOBSA-N
FDA UNII
42HK56048U

L-Tyrosine API
A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.
1 2D Structure

L-Tyrosine API

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
2.1.2 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
2.1.3 InChI Key
OUYCCCASQSFEME-QMMMGPOBSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1CC(C(=O)O)N)O
2.1.5 Isomeric SMILES
C1=CC(=CC=C1C[C@@H](C(=O)O)N)O
2.2 Other Identifiers
2.2.1 UNII
42HK56048U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. L Tyrosine

2. L-tyrosine

3. Para Tyrosine

4. Para-tyrosine

5. Tyrosine, L Isomer

6. Tyrosine, L-isomer

2.3.2 Depositor-Supplied Synonyms

1. L-tyrosine

2. 60-18-4

3. (s)-tyrosine

4. P-tyrosine

5. L-p-tyrosine

6. (2s)-2-amino-3-(4-hydroxyphenyl)propanoic Acid

7. H-tyr-oh

8. 4-hydroxy-l-phenylalanine

9. Tyrosine, L-

10. Tyrosinum [latin]

11. Tyrosine (van)

12. Tirosina [spanish]

13. L-(-)-tyrosine

14. (-)-alpha-amino-p-hydroxyhydrocinnamic Acid

15. L-phenylalanine, 4-hydroxy-

16. Beta-(p-hydroxyphenyl)alanine

17. Tyrosine [usan:inn]

18. Fema No. 3736

19. (s)-alpha-amino-4-hydroxybenzenepropanoic Acid

20. L-2-amino-3-p-hydroxyphenylpropanoic Acid

21. 3-(4-hydroxyphenyl)-l-alanine

22. (s)-3-(p-hydroxyphenyl)alanine

23. (s)-(-)-tyrosine

24. Hsdb 2003

25. Alpha-amino-beta-(4-hydroxyphenyl)propionic Acid

26. Ai3-09055

27. Tirosina

28. Propanoic Acid, 2-amino-3-(4-hydroxyphenyl)-, (s)-

29. Nsc 82624

30. Alpha-amino-p-hydroxyhydrocinnamic Acid, (-)-

31. L-tyr

32. (s)-2-amino-3-(4-hydroxyphenyl)propanoic Acid

33. (s)-2-amino-3-(p-hydroxyphenyl)propionic Acid

34. L-tyrosine, Monomer

35. Alpha-amino-4-hydroxybenzenepropanoic Acid, (s)-

36. 2-amino-3-(4-hydroxyphenyl)propanoic Acid, (s)-

37. Benzenepropanoic Acid, Alpha-amino-4-hydroxy-, (s)-

38. Mfcd00002606

39. Tyr

40. 25619-78-7

41. Chebi:17895

42. Nsc-82624

43. 42hk56048u

44. Ncgc00159350-02

45. Tyrosine (l-tyrosine)

46. Tyrosinum

47. Dsstox_cid_3730

48. L-tyrosin

49. (-)-.alpha.-amino-p-hydroxyhydrocinnamic Acid

50. Dsstox_rid_77170

51. Dsstox_gsid_23730

52. L-tyrosine, Homopolymer

53. Cas-60-18-4

54. L-tyrosine (9ci)

55. 4ts1

56. Tyrosine (usp/inn)

57. Einecs 200-460-4

58. Plovamer-acetate

59. Benzenepropanoate

60. Unii-42hk56048u

61. 2csm

62. (s)-2-amino-3-(4-hydroxyphenyl)propionic Acid

63. (l)-tyrosine

64. (-) Tyrosine

65. H-tyr

66. L-tyrosine,(s)

67. L-tyrosine (jp17)

68. Tyrosine [hsdb]

69. Tyrosine [inci]

70. Tyrosine [usan]

71. Tyrosine [inn]

72. Tyrosine [ii]

73. Tyrosine [mi]

74. L-tyr-oh

75. Tyrosine [vandf]

76. Tyrosine, L- (8ci)

77. .alpha.-amino-.beta.-(4-hydroxyphenyl)propionic Acid

78. L-tyrosine [fcc]

79. L-tyrosine [jan]

80. Melanin Synthesized From Tyr Substrate Catalyzed By Tyrosinase For 6 Hrs

81. Tyrosine [mart.]

82. Bmse000051

83. Chembl925

84. L-tyrosine [fhfi]

85. Tyrosine [who-dd]

86. Schembl1581

87. L-[u-14c]tyr

88. L-phenylalanine-4-hydroxy-

89. L-tyrosine Non-animal Source

90. L-tyrosine [usp-rs]

91. Levodopa Impurity, L-tyrosine-

92. Tyrosine [orange Book]

93. Gtpl4791

94. L-tyrosine, >=97%, Fg

95. Tyrosine [ep Monograph]

96. Dd69927c-c6a8-4bc6-8e9a-0ab423b176e7

97. Dtxsid1023730

98. Tyrosine [usp Monograph]

99. Bdbm18129

100. Zinc266964

101. N-acetyl-o-(dihydroxymethylsilyl)-

102. Hy-n0473

103. L-tyrosine, Vetec(tm), 98.5%

104. Levodopa Related Compound L-tyrosine

105. Tox21_111594

106. (-)-a-amino-p-hydroxyhydrocinnamate

107. Ac2634

108. S4608

109. Akos010400205

110. Tox21_111594_1

111. (s)-a-amino-4-hydroxybenzenepropanoate

112. Am82304

113. Cs-8013

114. Db00135

115. (-)-alpha-amino-p-hydroxyhydrocinnamate

116. (-)-a-amino-p-hydroxyhydrocinnamic Acid

117. (s)-3-(4-hydroxyphenyl)alanine

118. (s)-a-amino-4-hydroxy-benzenepropanoate

119. Ncgc00159350-03

120. Ncgc00344525-01

121. Ac-11295

122. As-11772

123. Bp-13285

124. Levodopa Impurity B [ep Impurity]

125. Melanin Synthesized From Tyr Substrate Catalyzed By Tyrosinase For 6 Hrs, Oxidized With Hydrogen Peroxide

126. Melanin Synthesized From Tyr Substrate Catalyzed By Tyrosinase For 6 Hrs, Oxidized With Hydrogen Peroxide, <3 Kd Fraction

127. Melanin Synthesized From Tyr Substrate Catalyzed By Tyrosinase, Brominated With N-bromosuccinimide

128. Melanin Synthesized From Tyr Substrate Catalyzed By Tyrosinase, Sulfonated Using Sulfur Trioxide/dmf Complex For 1.5-7 Hours

129. (s)-alpha-amino-4-hydroxybenzenepropanoate

130. Diethyl1,3,5-benzenetricarboxylate

131. L-tyrosine, Bioultra, >=99.0% (nt)

132. (s)-2-amino-3-(p-hydroxyphenyl)propionate

133. (s)-a-amino-4-hydroxybenzenepropanoic Acid

134. Db-029987

135. L-tyrosine, Free Base - Cas 60-18-4

136. (s)-a-amino-4-hydroxy-benzenepropanoic Acid

137. (s)-alpha-amino-4-hydroxy-benzenepropanoate

138. L-tyrosine, Reagent Grade, >=98% (hplc)

139. L-tyrosine, Saj Special Grade, >=99.0%

140. T0550

141. C00082

142. D00022

143. D70837

144. L-tyrosine, Vetec(tm) Reagent Grade, >=98%

145. M02963

146. (2s)-2-amino-3-(4-hydroxyphenyl)propanoicacid

147. (s)-alpha-amino-4-hydroxy-benzenepropanoic Acid

148. L-tyrosine, Cell Culture Reagent (h-l-tyr-oh)

149. (s)-.alpha.-amino-4-hydroxybenzenepropanoic Acid

150. 002t606

151. 2-amino-3-(4-hydroxyphenyl)propanoic Acid-(s)-

152. A832631

153. N-acetyltyrosine Impurity A [ep Impurity]

154. Q188017

155. J-521656

156. Propanoic Acid, 2-amino-3-(4-hydroxyphenyl)-(s)-

157. Levodopa Impurity, L-tyrosine- [usp Impurity]

158. Q27115106

159. Benzenepropanoic Acid, .alpha.-amino-4-hydroxy-, (s)-

160. F8889-8713

161. L-tyrosine, Certified Reference Material, Tracecert(r)

162. Tyrosine, European Pharmacopoeia (ep) Reference Standard

163. Z1250208672

164. L-tyrosine, United States Pharmacopeia (usp) Reference Standard

165. 2-amino-3-(4-hydroxyphen Yl)-2-amino-3-(4-hydroxyphenyl)-propanoate

166. 2-amino-3-(4-hydroxyphen Yl)-2-amino-3-(4-hydroxyphenyl)-propanoic Acid

167. Benzeneethanaminium,a-carboxy-4-hydroxy-n,n,n-trimethyl-,inner Salt,(as)-

168. Benzeneethanaminium, A-carboxy-4-hydroxy-n,n,n-trimethyl-,inner Salt, (as)-

169. 1189756-47-5

170. L-tyrosine, From Non-animal Source, Meets Ep, Usp Testing Specifications, Suitable For Cell Culture, >=99.0%

171. L-tyrosine, Pharmagrade, Ajinomoto, Ep, Jp, Usp, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 181.19 g/mol
Molecular Formula C9H11NO3
XLogP3-2.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass181.07389321 g/mol
Monoisotopic Mass181.07389321 g/mol
Topological Polar Surface Area83.6 Ų
Heavy Atom Count13
Formal Charge0
Complexity176
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Tyrosine is claimed to act as an effective antidepressant, however results are mixed. Tyrosine has also been claimed to reduce stress and combat narcolepsy and chronic fatigue, however these claims have been refuted by some studies.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tyrosine is a nonessential amino acid synthesized in the body from phenylalanine. Tyrosine is critical for the production of the body's proteins, enzymes and muscle tissue. Tyrosine is a precursor to the neurotransmitters norepinephrine and dopamine. It can act as a mood elevator and an anti-depressant. It may improve memory and increase mental alertness. Tyrosine aids in the production of melanin and plays a critical role in the production of thyroxin (thyroid hormones). Tyrosine deficiencies are manifested by hypothyroidism, low blood pressure and low body temperature. Supplemental tyrosine has been used to reduce stress and combat narcolepsy and chronic fatigue.


5.2 Absorption, Distribution and Excretion

Absorption

L-tyrosine is absorbed from the small intestine by a sodium-dependent active transport process.


Semi-chronic exposure of ICR male Mice to Aflatoxin B1 in non-toxic doses results in elevated lung tryptophan levels without change in serotonin or 5-hydroxyindole-3-acetic acid levels. This change is organ specific in that tryptophan levels are not altered in spleen, duodenum, heart or central nervous system. Acute (48 hr) flunixin treatment decreases lung tryptophan levels and reverses the Aflatoxin B1 mediated increase in lung tryptophan levels. On the other hand, flunixin treatment decreases central nervous system tryptophan levels in control mice but not in Aflatoxin B1 treated mice. Aflatoxin B1 treated mice have an increase in splenic serotonin content. Acute (48 hr) treatment of mice with E. coli lipopolysaccharide also increases splenic serotonin, and Aflatoxin B1 treatment followed by lipopolysaccharide have a slightly additive effect on spleen serotonin content. Treatment of mice with lipopolysaccharide increases heart serotonin, an effect which is not altered in Aflatoxin B1 pretreated mice. Both lipopolysaccharide and Aflatoxin B1 per se increases lung tyrosine levels although the combination of treatments is not significantly different from the control value. Flunixin treatment increases lung tyrosine levels, an effect which is not altered by Aflatoxin B1 pretreatment. Acute treatment with either lipopolysaccharide or flunixin decreases the central nervous system tryptophan/tyrosine ratio; pretreatment with Aflatoxin B1 prevents those changes in the central nervous system tryptophan/tyrosine ratio. Central nervous system catecholamines are reduced in Aflatoxin B1 pretreated mice. However, central nervous system catecholamine changes in Aflatoxin B1 treated mice are normalized by vitamin E supplementation during the treatment period.

PMID:1906975 Weekley LB; Metab Brain Dis 6 (1): 19-32 (1991)


Male Wistar rats were divided in free choice conditions into heavy-drinkers consuming greater than 3.5 g/kg of ethanol daily, and light-drinkers consuming less than 2.0 g/kg/day. Subsequent 30 day intragastric administration of 25% ethanol (8-11 g/kg/day) caused an increase in permeability of the blood brain barrier to 14(C)-tyrosine, 14(C)-tryptophan and 14(C)-DOPA at all the stages of alcoholization. All the changes were more pronounced in light-drinkers than in heavy- drinker rats. Disulfiram, and to a lesser extent phenazepam and diazepam, when repeatedly injected (for 16-30 days) together with ethanol aggravated its effects.

PMID:2118321 Borisenko SA; Ann Ist Super Sanita 26 (1): 39-42 (1990)


Effects of mercury chloride (100 uM) para-chloromercuribenzene sulfonate (1 uM), and oxophenylarsine (250 uM) were determined on (a) the rate of sodium pump activity in intact winter flounder intestine; (b) activity of sodium potassium ATPase in tissue homogenates; and (c) sodium-dependent and sodium independent uptake of tyrosine in brush border membrane vesicles. All three agents decreased cell potassium, although effects on cell potassium lagged behind those for inhibition of the ATPase. At the concentrations used in the Ussing chamber (or at one-tenth concentration), all agents completely inhibited sodium potassium ATPase activity in enzyme assays performed with tissue homogenates. In contrast, only mercury chloride decreased sodium dependent uptake of tyrosine by brush border membrane vesicles. These results suggest that mercurial and arsenical effects on tyrosine absorption are due to inhibition of the sodium potassium ATPase thus decreasing the driving force for the cellular uptake by the sodium tyrosine cotransport system. Direct effects on sodium tyrosine cotransport may play a role in the inhibition observed with mercury chloride, but not for para-chloromercuribenzene sulfonate or oxophenylarsine.

PMID:2163123 Musch MW et al; Toxicol Appl Pharmacol 104 (1): 59-66 (1990)


Female Sprague-Dawley rats were treated acutely (12-hr) with aflatoxin B1 (100 ug/kg ip) or vehicle (10% acetone in 0.9% sodium chloride) and regional brain levels of tryptophan, serotonin and tyrosine were assayed. Brainstem but not cerebellar or cortical tyrosine levels were decreased in aflatoxin B1-treated rats. Brain tryptophan was increased in all 3 brain regions by acute aflatoxin B1 treatment, while serotonin levels were unaltered in the cerebellum and cortex and decreased in the brainstem. These experiments indicate that acute aflatoxin B1 treatment differentially alters brain amino acids and serotonin and that changes in brain tryptophan, the serotonin precursor, do not parallel changes in brain serotonin.

PMID:2500755 Weekley LB et al; Toxicol Lett 47 (2): 173-7 (1989)


For more Absorption, Distribution and Excretion (Complete) data for L-TYROSINE (10 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

In the liver, L-tyrosine is involved in a number of biochemical reactions, including protein synthesis and oxidative catabolic reactions. L-tyrosine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body.


/METABOLIC PATHWAY FOR L-TYROSINE:/ /TYROSINE GIVES/ P-HYDROXYPHENYLPYRUVIC ACID GIVES CO2 + HOMOGENTISIC ACID GIVES MALEYLACETOACETIC ACID GIVES FUMARYLACETOACETIC ACID GIVES FUMARATE + ACETOACETATE; TYROSINE GIVES 3,4-DIHYDROXYPHENYLALANINE GIVES CO2 + 3,4-DIHYDROXYPHENYLETHYLAMINE GIVES NORADRENALIN GIVES ADRENALIN.

Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 832


L-TYROSINE GIVES N-ACETYL-L-TYROSINE IN MAN; GIVES 3-CARBOXY-L-TYROSINE IN RESEDA; GIVES P-COUMARIC ACID IN SUGAR CANE, L-TYROSINE GIVES PARA-CRESOL IN PROTEUS; GIVES 3,4-DIHYDROXY-L-PHENYLALANINE IN HAMSTER; GIVES 3,4-DIHYDROXYSTILBENE-2-CARBOXYLIC ACID IN HYDRANGEA, L-TYROSINE GIVES 2,7-DIMETHYLNAPHTHOQUINONE IN CHIMAPHILA; GIVES L-DITYROSINE IN BEEF; GIVES PARA-HYDROXYMANDELONITRILE IN SORGHUM, L-TYROSINE GIVES PARA-HYDROXYPHENYLACETALDOXIME IN AUBRETIA; GIVES PARA-HYDROXYPHENYLPYRUVIC ACID IN RAT; GIVES 3-IODO-L-TYROSINE IN BEEF; L-TYROSINE GIVES LACHNANTHOSIDE IN LACHNANTHES; LOPHOCERINE IN LOPHOCERUS; MESEMBRINE IN SCELETIUM; NARWEDINE IN DAFFODIL, L-TYROSINE GIVES NOVOBIOCIN IN STREPTOMYCES; PHENOL IN RAT; BETA-TOCOPHEROL IN ANABAENA; TYLOPHORINE IN TYLOPHORA, L-TYROSINE GIVES TYRAMINE IN RAT; GIVES BETA-TYROSINE IN BACILLUS; GIVES L-TYROSINE HYDROXAMATE IN BEEF. L-TYROSINE GIVES L-TYROSINE-4-PHOSPHATE IN FLY; GIVES XANTHOCILLIN IN PENICILLIUM. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. T-47


Metabolism of tyrosine was impaired after chronic alcoholization of rats with 10% ethanol within 10 months. Within the first 3-4 months activation of tyrosine aminotransferase and a decrease in phenylalanine hydroxylase activity were found in liver tissue. Activity of tyrosine aminotransferase was not increased during the long term alcohol intoxication. At the same time, activity of tyrosine aminotransferase was decreased within 5-6 months simultaneously with activation of phenylalanine hydroxylase. An increase in the alcohol dehydrogenase activity was also observed in rat liver tissue during the initial period of intoxication. The enzymatic activity was decreased beginning from the 3-4 months of the alcoholization and maintained at the low level. Hyperthermia augmented these alterations observed in chronic alcoholization of rats.

Kurbanov KhK, Romakh ON; Vopr Med Khim 35 (4): 102-5 (1989)


Spontaneous behavior subsequent to acute oral administration of high doses of aspartame, phenylalanine, or tyrosine was analyzed using a computer pattern recognition system. Spraque Dawley male rats (250-300 g) were dosed orally with aspartame (500 or 100 mg/kg), phenylalanine (281 or 562 mg/kg), or tyrosine (309 or 618 mg/kg), and their behavior was analyzed 1 hr after dosing. The computer pattern recognition system recorded and classifed 13 different behavioral acts performed by the animals during the first 15-min exploration of a novel environment. These doses of aspartame, phenylalanine, and tyrosine did not induce any significant changes in spontaneous behavior. Unlike low doses of amphetamine and despite high plasma concentrations of phenylalanine and tyrosine, no behavioral alteration was detected by the computer pattern recognition system.

PMID:1677339 Mullenix PJ et al; Fundam Appl Toxicol 16 (3): 495-505 (1991)


For more Metabolism/Metabolites (Complete) data for L-TYROSINE (7 total), please visit the HSDB record page.


5.4 Mechanism of Action

Tyrosine is produced in cells by hydroxylating the essential amino acid phenylalanine. This relationship is much like that between cysteine and methionine. Half of the phenylalanine required goes into the production of tyrosine; if the diet is rich in tyrosine itself, the requirements for phenylalanine are reduced by about 50%. The mechanism of L-tyrosine's antidepressant activity can be accounted for by the precursor role of L-tyrosine in the synthesis of the neurotransmitters norepinephrine and dopamine. Elevated brain norepinephrine and dopamine levels are thought to be associated with antidepressant effects.


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