Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:34 UTC |
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Update date | 2019-11-26 02:54:49 UTC |
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Primary ID | FDB000446 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Tyrosine |
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Description | L-Tyrosine, also known as Tyr or tirosina, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Tyrosine is an odorless tasting compound. L-Tyrosine is found, on average, in the highest concentration within a few different foods, such as casein, milk (cow), and other soy product and in a lower concentration in waffle, cracker, and garden tomato (var.). L-Tyrosine has also been detected, but not quantified in, several different foods, such as hawthorns (Crataegus), sourdough, root vegetables, ohelo berries (Vaccinium reticulatum), and black raisin. This could make L-tyrosine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on L-Tyrosine. |
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CAS Number | 60-18-4 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Amino-3-(4-hydroxyphenyl)propanoic acid | ChEBI | 2-Amino-3-(p-hydroxyphenyl)propionic acid | ChEBI | 3-(p-Hydroxyphenyl)alanine | ChEBI | Tirosina | ChEBI | Tyr | ChEBI | Tyrosin | ChEBI | Y | ChEBI | 2-Amino-3-(4-hydroxyphenyl)propanoate | Generator | 2-Amino-3-(p-hydroxyphenyl)propionate | Generator | (-)-α-amino-p-hydroxyhydrocinnamic acid | biospider | (-)-a-amino-p-hydroxyhydrocinnamate | biospider | (-)-a-amino-p-hydroxyhydrocinnamic acid | biospider | (-)-alpha-amino-p-hydroxyhydrocinnamate | biospider | (-)-alpha-amino-p-hydroxyhydrocinnamic acid | biospider | (-)-α-amino-P-hydroxyhydrocinnamate | Generator | (-)-α-amino-P-hydroxyhydrocinnamic acid | Generator | (2S)-2-amino-3-(4-Hydroxyphenyl)propanoate | Generator | (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid | biospider | (s)-(-)-tyrosine | biospider | (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid | biospider | (S)-2-Amino-3-(p-hydroxyphenyl)propionate | biospider | (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid | biospider | (S)-3-(p-Hydroxyphenyl)alanine | biospider | (S)-a-amino-4-hydroxy-Benzenepropanoate | biospider | (S)-a-amino-4-hydroxy-Benzenepropanoic acid | biospider | (S)-a-Amino-4-hydroxybenzenepropanoate | biospider | (S)-a-Amino-4-hydroxybenzenepropanoic acid | biospider | (S)-alpha-amino-4-hydroxy-Benzenepropanoate | biospider | (S)-alpha-amino-4-hydroxy-Benzenepropanoic acid | biospider | (S)-alpha-Amino-4-hydroxybenzenepropanoate | biospider | (S)-alpha-Amino-4-hydroxybenzenepropanoic acid | biospider | (s)-tyrosine | biospider | (S)-α-amino-4-hydroxybenzenepropanoate | Generator | (S)-α-amino-4-hydroxybenzenepropanoic acid | Generator | α-amino-α-amino-p-hydroxyhydrocinnamic acid | biospider | α-Amino-β-(4-hydroxyphenyl)propionic acid | biospider | 2-amino-3-(4-Hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoate | HMDB | 2-amino-3-(4-Hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acid | HMDB | 2-Amino-3-(4-hydroxyphenyl)propanoic acid-(S)- | biospider | 2-Amino-3-(4-hydroxyphenyl)propanoic acid, (S)- | biospider | 3-(4-Hydroxyphenyl)-L-alanine | biospider | 4-Hydroxy-L-phenylalanine | ChEBI | alpha-Amino-4-hydroxybenzenepropanoic acid, (S)- | biospider | Alpha-amino-p-hydroxyhydrocinnamic acid, (-)- | biospider | Benzenepropanoate | HMDB | Benzenepropanoic acid, α-amino-4-hydroxy-, (S)- | biospider | Benzenepropanoic acid, alpha-amino-4-hydroxy-, (S)- | biospider | FEMA 3736 | db_source | L-2-Amino-3-p-hydroxyphenylpropanoic acid | biospider | L-p-tyrosine | biospider | L-Phenylalanine-4-hydroxy- | biospider | L-Phenylalanine, 4-hydroxy- | biospider | L-Tyrosin | ChEBI | L-Tyrosine | manual | L-Tyrosine (9CI) | biospider | P-Tyrosine | HMDB | Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)- | biospider | TYR | biospider | TYROSINE | ChEBI | Tyrosine, 9CI, 8CI; L-form | db_source | Tyrosine, L- (8CI) | biospider |
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Predicted Properties | |
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Chemical Formula | C9H11NO3 |
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IUPAC name | 2-amino-3-(4-hydroxyphenyl)propanoic acid |
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InChI Identifier | 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) |
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InChI Key | OUYCCCASQSFEME-UHFFFAOYSA-N |
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Isomeric SMILES | NC(CC1=CC=C(O)C=C1)C(O)=O |
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Average Molecular Weight | 181.1885 |
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Monoisotopic Molecular Weight | 181.073893223 |
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Classification |
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Description | Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Tyrosine and derivatives |
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Alternative Parents | |
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Substituents | - Tyrosine or derivatives
- Phenylalanine or derivatives
- 3-phenylpropanoic-acid
- Amphetamine or derivatives
- Alpha-amino acid
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic nitrogen compound
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Foods | Dairy productsEggsMeats Grains: Nuts and legumes: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 59.66%; H 6.12%; N 7.73%; O 26.49% | DFC |
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Melting Point | Mp 314-318 dec. approx. (rapid heat) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.479 mg/mL at 25 oC | SEIDELL,A (1941) |
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Experimental logP | -2.26 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa3 10.07 (phenolic OH) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -9.01 (11.6% KOH) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-3900000000-7a26097fda66f2f445b5 | 2014-09-20 | View Spectrum | Predicted GC-MS | L-Tyrosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4r-4900000000-fb040ac104208d200d8c | Spectrum | Predicted GC-MS | L-Tyrosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Tyrosine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9200000000-2547dae1665803f38bd1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00rf-6900000000-b2b0f8f68423fbfd602c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Negative | splash10-001i-0900000000-3a614a31d778b5df1dc5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-014r-0900000000-e0fcbbd1a3428bca9ec3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-000i-0900000000-68cd9dcfb64ff4fab197 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00kr-0900000000-03fe77841e11d74f5df7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0900000000-4a714f9a050c975b9c94 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-014i-0900000000-dceaa0a6a4997d0a9e6d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 25V, Positive | splash10-014r-0900000000-4c7edd239a412ca97d14 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-2c0f9a585c243ecc645f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-ecbde0599ce71965579a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-014i-0900000000-39abc09c5fc3d275d44b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-00kr-0900000000-00cb1ae859c330a9a3be | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-0900000000-4902904e7400106e84d5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9200000000-290ac7df2e0f388c56ae | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9700000000-194f27fb6aa928ff0650 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-002f-9000000000-d55fb2db34d35408a084 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00rf-6900000000-f692bfce6e48ce195419 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 25V, Positive | splash10-00kr-0900000000-87801ed16c51bc9eea00 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q0-0900000000-64b5df3e494e5df5c1be | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-c38735d64e2a16bd0c68 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-6900000000-6696908ff67c37922f99 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-941af648c85b3f0f7c66 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01q9-1900000000-b7d3075f2496303aeb37 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fr-9700000000-c242deae91617b5e8735 | 2015-05-27 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 5833 |
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ChEMBL ID | CHEMBL925 |
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KEGG Compound ID | C00082 |
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Pubchem Compound ID | 6057 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17895 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03839 |
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HMDB ID | HMDB00158 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCN92-M:BCK50-J |
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EAFUS ID | 3789 |
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Dr. Duke ID | TYROSINE|L-(-)-TYROSINE |
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BIGG ID | 33785 |
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KNApSAcK ID | C00001397 |
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HET ID | TYR |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1037771 |
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SuperScent ID | Not Available |
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Wikipedia ID | L-Tyrosine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Aromatic-L-amino-acid decarboxylase | DDC | P20711 | Tyrosine 3-monooxygenase | TH | P07101 | Tyrosine aminotransferase | TAT | P17735 | Phenylalanine-4-hydroxylase | PAH | P00439 | Aspartate aminotransferase, cytoplasmic | GOT1 | P17174 | Aspartate aminotransferase, mitochondrial | GOT2 | P00505 | Tyrosine--tRNA ligase, cytoplasmic | YARS | P54577 | Tyrosine--tRNA ligase, mitochondrial | YARS2 | Q9Y2Z4 | Basic fibroblast growth factor receptor 1 | FGFR1 | P11362 | Epidermal growth factor receptor | EGFR | P00533 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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odorless |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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