ChemSpider 2D Image | L-(-)-Tyrosine | C9H11NO3

L-(-)-Tyrosine

  • Molecular FormulaC9H11NO3
  • Average mass181.189 Da
  • Monoisotopic mass181.073898 Da
  • ChemSpider ID5833
  • defined stereocentres - 1 of 1 defined stereocentres


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L-(-)-Tyrosine
(S)-(-)-Tyrosine
(S)-2-Amino-3-(4-hydroxyphenyl)propionic acid
(S)-a-amino-4-hydroxy-Benzenepropanoic acid
(S)-a-Amino-4-hydroxybenzenepropanoic acid
(S)-tyrosine
(S)-α-amino-4-hydroxy-Benzenepropanoic acid
3-(4-Hydroxyphenyl)-L-alanine
60-18-4 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

3736 [DBID]
42HK56048U [DBID]
MFCD00002606 [DBID]
855456_ALDRICH [DBID]
93829_FLUKA [DBID]
93840_FLUKA [DBID]
AI3-09055 [DBID]
AIDS018692 [DBID]
AIDS-018692 [DBID]
AIDS192301 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Colourless silky needles or white crystalline powder; odourless Food and Agriculture Organization of the United Nations L-Tyrosine
      white crystals or powder OU Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong oxidizing agents, strong reducing agents. OU Chemical Safety Data (No longer updated) More details
    • Toxicity:

      Organic Compound; Amine; Drug; Food Toxin; Dietary Supplement; Micronutrient; Metabolite; Nutraceutical; Animal Toxin; Natural Compound; Supplement; Non-Essential Amino Acid Toxin, Toxin-Target Database T3D4371
      ORL-RAT LD50 > 5110 mg kg-1 OU Chemical Safety Data (No longer updated) More details
    • Safety:

      26-37 Alfa Aesar [A13740] , A11141
      36/37/38 Alfa Aesar [A13740] , A11141
      H315-H319-H335 Alfa Aesar A11141
      Irritant SynQuest 4757-1-X2, 63281
      Minimize exposure. OU Chemical Safety Data (No longer updated) More details
      P261-P305+P351+P338-P302+P352-P321-P405-P501a Alfa Aesar A11141
      Warning Alfa Aesar A11141
      WARNING: Not for human consumption, may irriate skin & eyes. Alfa Aesar A11141
      WARNING: Not sold for human treatment, trials or use Alfa Aesar A11141
      Xi Abblis Chemicals AB1002647
    • Chemical Class:

      An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of <stereo>L</stereo>-tyrosine; major species at pH 7.3. ChEBI CHEBI:17895, CHEBI:32759, CHEBI:58315
      An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of L-tyrosine; major species at pH 7.3. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:58315
      An optically active form of tyrosine having <stereo>L</stereo>-configuration. ChEBI CHEBI:17895, CHEBI:32759, CHEBI:58315
      An optically active form of tyrosine having L-configuration. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17895
    • Compound Source:

      (S)-reticuline biosynthesis I PlantCyc TYR
      4-hydroxybenzoate biosynthesis I (eukaryotes) PlantCyc TYR
      4-hydroxyphenylpyruvate biosynthesis PlantCyc TYR
      Aegilops tauschii PlantCyc TYR
      Amaranthus hypochondriacus PlantCyc TYR
      Amaryllidacea alkaloids biosynthesis PlantCyc TYR
      Amborella trichopoda PlantCyc TYR
      Anacardium occidentale PlantCyc TYR
      Ananas comosus PlantCyc TYR
      Aquilegia coerulea PlantCyc TYR
      Arabidopsis halleri PlantCyc TYR
      Arabidopsis lyrata PlantCyc TYR
      Arabidopsis thaliana col PlantCyc TYR
      Asparagus officinalis PlantCyc TYR
      Beta vulgaris subsp. vulgaris PlantCyc TYR
      betacyanin biosynthesis PlantCyc TYR
      betalamic acid biosynthesis PlantCyc TYR
      betaxanthin biosynthesis (via dopaxanthin) PlantCyc TYR
      Boechera stricta PlantCyc TYR
      Brachypodium distachyon PlantCyc TYR
      Brassica napus PlantCyc TYR
      Brassica oleracea var. capitata PlantCyc TYR
      Brassica oleracea var. oleracea PlantCyc TYR
      Brassica rapa FPsc PlantCyc TYR
      Brassica rapa subsp. pekinensis PlantCyc TYR
      Calotropis gigantea PlantCyc TYR
      Camptotheca acuminata PlantCyc TYR
      Cannabis sativa PlantCyc TYR
      Capsella grandiflora PlantCyc TYR
      Capsella rubella PlantCyc TYR
      Capsicum annuum PlantCyc TYR
      Carica papaya PlantCyc TYR
      Catharanthus roseus PlantCyc TYR
      Chenopodium quinoa PlantCyc TYR
      Chlamydomonas reinhardtii PlantCyc TYR
      Chromochloris zofingiensis PlantCyc TYR
      Cicer arietinum PlantCyc TYR
      Citrus clementina PlantCyc TYR
      Citrus sinensis PlantCyc TYR
      Coccomyxa subellipsoidea C-169 PlantCyc TYR
      Corchorus capsularis PlantCyc TYR
      coumarins biosynthesis (engineered) PlantCyc TYR
      Cucumis sativus PlantCyc TYR
      Daucus carota subsp. sativus PlantCyc TYR
      dhurrin biosynthesis PlantCyc TYR
      Dianthus caryophyllus PlantCyc TYR
      Dioscorea rotundata PlantCyc TYR
      Eucalyptus grandis PlantCyc TYR
      Eutrema salsugineum PlantCyc TYR
      Fragaria vesca subsp. vesca PlantCyc TYR
      Glycine max PlantCyc TYR
      Gossypium raimondii PlantCyc TYR
      Helianthus annuus PlantCyc TYR
      Hordeum vulgare subsp. vulgare PlantCyc TYR
      Humulus lupulus var. lupulus PlantCyc TYR
      hydroxycinnamic acid tyramine amides biosynthesis PlantCyc TYR
      Kalanchoe fedtschenkoi PlantCyc TYR
      Kalanchoe laxiflora PlantCyc TYR
      L-dopa and L-dopachrome biosynthesis PlantCyc TYR
      Leersia perrieri PlantCyc TYR
      Linum usitatissimum PlantCyc TYR
      Lotus japonicus PlantCyc TYR
      L-phenylalanine biosynthesis III (cytosolic, plants) PlantCyc TYR
      L-phenylalanine degradation V PlantCyc TYR
      L-tyrosine + 2 a reduced [NADPH-hemoprotein reductase] + 2 oxygen -> (E)-(4-hydroxyphenyl)acetaldehyde oxime + 2 an oxidized [NADPH-hemoprotein reductase] + CO2 + 3 H2O PlantCyc TYR
      L-tyrosine + oxygen -> dopaquinone + H2O PlantCyc TYR
      L-tyrosine biosynthesis I PlantCyc TYR
      L-tyrosine biosynthesis II PlantCyc TYR
      L-tyrosine biosynthesis III PlantCyc TYR
      L-tyrosine degradation I PlantCyc TYR
      Malus domestica PlantCyc TYR
      Manihot esculenta PlantCyc TYR
      Marchantia polymorpha PlantCyc TYR
      Medicago truncatula PlantCyc TYR
      Micromonas commoda RCC299 PlantCyc TYR
      Micromonas pusilla CCMP1545 PlantCyc TYR
      Mimulus guttatus PlantCyc TYR
      Miscanthus sinensis PlantCyc TYR
      Musa acuminata PlantCyc TYR
      naringenin biosynthesis (engineered) PlantCyc TYR
      Nicotiana tabacum PlantCyc TYR
      Olea europaea var. sylvestris PlantCyc TYR
      Oropetium thomaeum PlantCyc TYR
      Oryza brachyantha PlantCyc TYR
      Oryza glaberrima PlantCyc TYR
      Oryza punctata PlantCyc TYR
      Oryza rufipogon PlantCyc TYR
      Oryza sativa Japonica Group PlantCyc TYR
      Ostreococcus lucimarinus PlantCyc TYR
      Panicum hallii PlantCyc TYR
      Panicum virgatum PlantCyc TYR
      Petunia axillaris PlantCyc TYR
      Phaseolus vulgaris PlantCyc TYR
      Physcomitrella patens PlantCyc TYR
      Populus trichocarpa PlantCyc TYR
      Prunus persica PlantCyc TYR
      Ricinus communis PlantCyc TYR
      Rosa chinensis PlantCyc TYR
      Rosa multiflora PlantCyc TYR
      rosmarinic acid biosynthesis I PlantCyc TYR
      rosmarinic acid biosynthesis II PlantCyc TYR
      salidroside biosynthesis PlantCyc TYR
      Salvia miltiorrhiza PlantCyc TYR
      Selaginella moellendorffii PlantCyc TYR
      Setaria italica PlantCyc TYR
      Setaria viridis PlantCyc TYR
      Solanum lycopersicum PlantCyc TYR
      Solanum melongena PlantCyc TYR
      Solanum pennellii PlantCyc TYR
      Solanum tuberosum PlantCyc TYR
      Sorghum bicolor PlantCyc TYR
      Sphagnum fallax PlantCyc TYR
      Spinacia oleracea PlantCyc TYR
      Spirodela polyrhiza PlantCyc TYR
      taxiphyllin biosynthesis PlantCyc TYR
      Thellungiella parvula PlantCyc TYR
      Theobroma cacao PlantCyc TYR
      Trifolium pratense PlantCyc TYR
      Triticum aestivum PlantCyc TYR
      Triticum urartu PlantCyc TYR
      Vitis vinifera PlantCyc TYR
      Volvox carteri PlantCyc TYR
      Zea mays subsp. mays PlantCyc TYR
      Zostera marina PlantCyc TYR
    • Bio Activity:

      2 L-tyrosine + oxygen -> 2 L-dopa PlantCyc TYR
      an N10-formyl-tetrahydrofolate + L-phenylalanine + L-phenylalanine + an N10-formyl-tetrahydrofolate + oxygen + oxygen -> L-tyrosine + a 10-formyltetrahydrofolate-4a-carbinolamine + a 10-formyltetrahydrofolate-4a-carbinolamine + L-tyrosine PlantCyc TYR
      keto-phenylpyruvate + L-tyrosine <--> L-phenylalanine + 4-hydroxyphenylpyruvate PlantCyc TYR
      L-arogenate + NAD+ -> L-tyrosine + CO2 + NADH PlantCyc TYR
      L-arogenate + NADP+ -> L-tyrosine + CO2 + NADPH PlantCyc TYR
      L-phenylalanine + an N10-formyl-tetrahydrofolate + oxygen -> a 10-formyltetrahydrofolate-4a-carbinolamine + L-tyrosine PlantCyc TYR
      L-tyrosine -> 4-coumarate + ammonium PlantCyc TYR
      L-tyrosine + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + oxygen -> L-dopa + (6R)-4a-hydroxy-tetrahydrobiopterin PlantCyc TYR
      L-tyrosine + 2-oxoglutarate <--> 4-hydroxyphenylpyruvate + L-glutamate PlantCyc TYR
      L-tyrosine + 2-oxoglutarate <--> L-glutamate + 4-hydroxyphenylpyruvate PlantCyc TYR
      L-tyrosine + a reduced [NADPH-hemoprotein reductase] + oxygen -> N-hydroxy-L-tyrosine + an oxidized [NADPH-hemoprotein reductase] + H2O + H+ PlantCyc TYR
      L-tyrosine + betalamate -> portulacaxanthin II + H+ + H2O PlantCyc TYR
      L-tyrosine + FADH2 + oxygen -> L-dopa + FAD + H2O + H+ PlantCyc TYR
      L-tyrosine + H+ -> CO2 + tyramine PlantCyc TYR
      L-tyrosine + keto-phenylpyruvate + keto-phenylpyruvate + L-tyrosine <--> 4-hydroxyphenylpyruvate + L-phenylalanine + L-phenylalanine + 4-hydroxyphenylpyruvate PlantCyc TYR
      L-tyrosine + oxygen -> dopaquinone + H2O PlantCyc TYR

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.3±0.1 g/cm3
Boiling Point: 385.2±32.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 66.9±3.0 kJ/mol
Flash Point: 186.7±25.1 °C
Index of Refraction: 1.614
Molar Refractivity: 47.4±0.3 cm3
#H bond acceptors: 4
#H bond donors: 4
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.38
ACD/LogD (pH 5.5): -2.23
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.24
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 84 Å2
Polarizability: 18.8±0.5 10-24cm3
Surface Tension: 65.7±3.0 dyne/cm
Molar Volume: 135.9±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -1.76
    Log Kow (Exper. database match) =  -2.26
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  -2.04
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  384.29  (Adapted Stein & Brown method)
    Melting Pt (deg C):  248.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.85E-009  (Modified Grain method)
    MP  (exp database):  325 dec deg C
    Subcooled liquid VP: 4.54E-006 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  9.71e+004
       log Kow used: -2.04 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  479 mg/L (25 deg C)
        Exper. Ref:  SEIDELL,A (1941)
     Water Sol (Exper. database match) =  453 mg/L (25 deg C)
        Exper. Ref:  CRC HANDBOOK
     Water Sol (Exper. database match) =  400 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  94372 mg/L
    Wat Sol (Exper. database match) =  479.00
       Exper. Ref:  SEIDELL,A (1941)
    Wat Sol (Exper. database match) =  453.00
       Exper. Ref:  CRC HANDBOOK
    Wat Sol (Exper. database match) =  400.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines-acid
       Phenols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.25E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.542E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.04  (exp database)
  Log Kaw used:  -12.292  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.252
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0583
   Biowin2 (Non-Linear Model)     :   0.9753
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1693  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9863  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3783
   Biowin6 (MITI Non-Linear Model):   0.2478
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6115
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.000605 Pa (4.54E-006 mm Hg)
  Log Koa (Koawin est  ): 10.252
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00496 
       Octanol/air (Koa) model:  0.00439 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.152 
       Mackay model           :  0.284 
       Octanol/air (Koa) model:  0.26 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  80.0557 E-12 cm3/molecule-sec
      Half-Life =     0.134 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.603 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.218 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  97.15
      Log Koc:  1.987 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -2.04 (expkow database)

 Volatilization from Water:
    Henry LC:  1.25E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.305E+010  hours   (2.627E+009 days)
    Half-Life from Model Lake : 6.878E+011  hours   (2.866E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       1.17e-006       3.21         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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