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60-18-4 molecular structure
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(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid

ChemBase ID: 21
Molecular Formular: C9H11NO3
Molecular Mass: 181.18854
Monoisotopic Mass: 181.07389322
SMILES and InChIs

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

Cite this record

CBID:21 http://www.chembase.cn/molecule-21.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
IUPAC Traditional name
L-tyrosine
Brand Name
Rxosine
Tyrosine
Tyrosine Power
Synonyms
2-Amino-3-(p-hydroxyphenyl)propionic acid
3-(p-Hydroxyphenyl)alanine
Free-Form L-Tyrosine
β-p-Hydroxyphenylalanine
L-2-Amino-3-(4-hydroxyphenyl)propionic acid
2-AMINO-3-HYDROXYBUTYRIC ACID
L-TYROSINE, U.S.P.
3-(4-Hydroxyphenyl)-L-alanine
L-2-Amino-3-(4-hydroxyphenyl)propanoic acid
POLY-L-TYROSINE
(S)-2-Amino-3-(4-hydroxyphenyl)propionic acid
L-Tyrosine
L-Tyrosine
(S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Tyrosine
H-Tyr-OH
(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
CAS Number
60-18-4
556-03-6
EC Number
200-460-4
MDL Number
MFCD00002606
Beilstein Number
392441
Merck Index
149839
PubChem SID
24901863
160963484
24889931
24900164
24900206
24900543
46507885
PubChem CID
6057
1153
CHEBI ID
58315
CHEMBL
925
Chemspider ID
5833
DrugBank ID
DB03839
FEMA ID
3736
Wikipedia Title
Tyrosine
Flavis Number
17.022

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.9998473  H Acceptors
H Donor LogD (pH = 5.5) -1.4884841 
LogD (pH = 7.4) -1.495157  Log P -1.488594 
Molar Refractivity 47.0972 cm3 Polarizability 18.512522 Å3
Polar Surface Area 83.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.39  LOG S -1.37 
Solubility (Water) 7.67e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble0.5 M, clear, colorless (hot) expand Show data source
1 M HCl: soluble25 mg/mL expand Show data source
Slightly soluble expand Show data source
Apperance
powder expand Show data source
Melting Point
>300 °C (dec.)(lit.) expand Show data source
>300°C expand Show data source
255-257°C expand Show data source
342-344°C expand Show data source
Density
1.4 g/ml expand Show data source
1.46 expand Show data source
Optical Rotation
[α]20/D -10.6°, c = 4 in 1 M HCl expand Show data source
[α]20/D -11.5±1.0°, c = 4% in 1 M HCl expand Show data source
-11 (c=4 in 1N HCl) expand Show data source
Hydrophobicity(logP)
-1.8 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
YP2275600 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
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German water hazard class
1 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
room temp expand Show data source
Purity
≥97% expand Show data source
≥98% (HPLC) expand Show data source
≥99% expand Show data source
≥99.0% expand Show data source
≥99.0% (NT) expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
NI expand Show data source
reagent grade expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Optical Purity
ee: 98% (GLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Packaging
pkg of 1 g expand Show data source
Suitability
meets EP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.1% expand Show data source
≤0.1% (as SO4) expand Show data source
Impurities
≤0.5% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Ca: ≤100 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤100 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤200 mg/kg expand Show data source
NH4+: ≤200 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤250 mg/kg expand Show data source
chloride (Cl-): ≤400 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤300 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Loss on Drying
≤0.2% loss on drying, 20 °C (HV) expand Show data source
≤0.5% loss on drying, 110 °C expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
Product Line
BioUltra expand Show data source
abs.
absorption0.5M/310 nm, 1 M HCl cut-off expand Show data source
Pharmacopeia Traceability
traceable to PhEur T2900000 expand Show data source
traceable to USP 1705006 expand Show data source
Linear Formula
4-(HO)C6H4CH2CH(NH2)CO2H expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia DrugBank DrugBank
MP Biomedicals - 02103183 external link
Crystalline
Free Base
MP Biomedicals - 02194759 external link
Cell Culture Reagent
Free Base
Crystalline
MP Biomedicals - 02199541 external link
Solid
MP Biomedicals - 05218193 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - 93829 external link
Other Notes
Amino acid precursor of dopamine and other catecholamines
Growth requirements of various microorganisms1
Sigma Aldrich - T4321 external link
Other Notes
Amino acid precursor of dopamine and other catecholamines
Packaging
Manufactured and packaged under cGMP
Sigma Aldrich - 30-5530 external link
Other Notes
Amino acid precursor of dopamine and other catecholamines
Sigma Aldrich - T90409 external link
Other Notes
Amino acid precursor of dopamine and other catecholamines
Sigma Aldrich - 93830 external link
Other Notes
Amino acid precursor of dopamine and other catecholamines
Sigma Aldrich - PHR1097 external link
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 external link
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 - W373605 external link
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 - T8566 external link
Other Notes
Amino acid precursor of dopamine and other catecholamines
Packaging
10 mg in autosmp vl
Sigma Aldrich - 91515 external link
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
DrugBank - DB00135 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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