(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid

• ChemBase ID: 21
• Molecular Formular: C9H11NO3
• Molecular Mass: 181.18854
• Monoisotopic Mass: 181.07389322
• SMILES: OC(=O)[C@@H](N)Cc1ccc(O)cc1
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(cc1)O)N
• 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
• InChIKey: OUYCCCASQSFEME-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: L-tyrosine
• Brand Name: Rxosine; Tyrosine; Tyrosine Power
• Synonyms: H-Tyr-OH; 2-Amino-3-(p-hydroxyphenyl)propionic acid; 3-(p-Hydroxyphenyl)alanine; Free-Form L-Tyrosine; L-Tyrosine; β-p-Hydroxyphenylalanine; L-2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)-L-alanine; 2-AMINO-3-HYDROXYBUTYRIC ACID; L-TYROSINE, U.S.P.; POLY-L-TYROSINE; L-2-Amino-3-(4-hydroxyphenyl)propanoic acid; Tyrosine; (S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid; L-Tyrosine; (S)-2-氨基-3-对羟苯基丙酸; 3-(4-对羟苯基)-L-丙氨酸; L-酪氨酸

Database IDs

• CAS Number: 60-18-4; 556-03-6
• EC Number: 200-460-4
• MDL Number: MFCD00002606
• Beilstein Number: 392441
• Merck Index: 149839
• PubChem SID: 24900543; 24889931; 160963484; 24900206; 24901863; 24900164; 46507885
• PubChem CID: 1153; 6057
• CHEBI ID: 58315
• CHEMBL: 925
• Chemspider ID: 5833
• DrugBank ID: DB03839
• FEMA ID: 3736
• Wikipedia Title: Tyrosine
• Flavis Number: 17.022

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9998473
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.4884841
• LogD (pH = 7.4): -1.495157
• Log P: -1.488594
• Molar Refractivity: 47.0972 cm^3
• Polarizability: 18.512522 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.39
• LOG S: -1.37
• Solubility (Water): 7.67e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble0.5 M, clear, colorless (hot); 1 M HCl: soluble25 mg/mL; Slightly soluble
• Apperance: powder
• Melting Point: >300 °C (dec.)(lit.); >300°C; 255-257°C; 342-344°C
• Density: 1.4 g/ml; 1.46
• Optical Rotation: [α]20/D -10.6°, c = 4 in 1 M HCl; [α]20/D -11.5±1.0°, c = 4% in 1 M HCl; -11 (c=4 in 1N HCl)
• Hydrophobicity(logP): -1.8

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: YP2275600
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Product Information

• Purity: ≥97%; ≥98% (HPLC); ≥99%; ≥99.0%; ≥99.0% (NT); 97%; 98%; 99%
• Grade: certified reference material; EP; NI; reagent grade; SAJ special grade; TraceCERT®; USP
• Optical Purity: ee: 98% (GLC)
• Packaging: pkg of 1 g
• Suitability: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.1%; ≤0.1% (as SO4)
• Impurities: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Ca: ≤100 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤100 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤200 mg/kg; NH4+: ≤200 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤250 mg/kg; chloride (Cl-): ≤400 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤300 mg/kg
• Biological Source: from non-animal source
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤0.2% loss on drying, 20 °C (HV); ≤0.5% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• Product Line: BioUltra
• abs.: absorption0.5M/310 nm, 1 M HCl cut-off
• Pharmacopeia Traceability: traceable to PhEur T2900000; traceable to USP 1705006
• Linear Formula: 4-(HO)C6H4CH2CH(NH2)CO2H
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05218193

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02199541

Solid

MP Biomedicals - 02194759

Cell Culture Reagent
Free Base
Crystalline

MP Biomedicals - 02103183

Crystalline
Free Base

DrugBank - DB00135

• Drug Groups: approved; nutraceutical
• Description: A non-essential amino acid. In animals it is synthesized from phenylalanine. It is also the precursor of epinephrine; thyroid hormones; and melanin. [PubChem]
• 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.
• 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.
• Toxicity: L-Tyrosine has very low toxicity. There have been very few reports of toxicity. LD₅₀ (oral, rat) > 5110 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: L-tyrosine is absorbed from the small intestine by a sodium-dependent active transport process.
• References: Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL: Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem. 2006 Dec 8;281(49):37877-87. Epub 2006 Oct 17. [Pubmed] ; Molnar GA, Wagner Z, Marko L, Ko Szegi T, Mohas M, Kocsis B, Matus Z, Wagner L, Tamasko M, Mazak I, Laczy B, Nagy J, Wittmann I: Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005 Nov;68(5):2281-7. [Pubmed] ; Molnar GA, Nemes V, Biro Z, Ludany A, Wagner Z, Wittmann I: Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic Res. 2005 Dec;39(12):1359-66. [Pubmed]
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - T8566

Other Notes
Amino acid precursor of dopamine and other catecholamines
Packaging
10 mg in autosmp vl

Sigma Aldrich - 93829

Other Notes
Amino acid precursor of dopamine and other catecholamines
Growth requirements of various microorganisms1

Sigma Aldrich - T4321

Other Notes
Amino acid precursor of dopamine and other catecholamines
Packaging
Manufactured and packaged under cGMP

Sigma Aldrich - W373605

Other Notes
Amino acid precursor of dopamine and other catecholamines
Packaging
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum

Sigma Aldrich - T90409

Other Notes
Amino acid precursor of dopamine and other catecholamines

Sigma Aldrich - 91515

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Other Notes
Amino acid precursor of dopamine and other catecholamines
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 93830

Other Notes
Amino acid precursor of dopamine and other catecholamines

Sigma Aldrich - PHR1097

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Amino acid precursor of dopamine and other catecholamines
Values of analytes vary lot to lot.

Sigma Aldrich - T3754

Other Notes
Amino acid precursor of dopamine and other catecholamines
Packaging
1 kg in poly bottle
50, 100, 500 g in poly bottle

Sigma Aldrich - 30-5530

Other Notes
Amino acid precursor of dopamine and other catecholamines

REFERENCES

• Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL: Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem. 2006 Dec 8;281(49):37877-87. Epub 2006 Oct 17. Pubmed
• Molnar GA, Wagner Z, Marko L, Ko Szegi T, Mohas M, Kocsis B, Matus Z, Wagner L, Tamasko M, Mazak I, Laczy B, Nagy J, Wittmann I: Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005 Nov;68(5):2281-7. Pubmed
• Molnar GA, Nemes V, Biro Z, Ludany A, Wagner Z, Wittmann I: Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic Res. 2005 Dec;39(12):1359-66. Pubmed