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Record Information
Version1.0
Creation Date2016-09-30 22:20:19 UTC
Update Date2020-06-04 21:55:45 UTC
MCDB ID BMDB0000158
Secondary Accession Numbers
  • BMDB00158
Metabolite Identification
Common NameL-Tyrosine
DescriptionL-Tyrosine, also known as (S)-tyrosine or para tyrosine, 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Tyrosine exists in all living species, ranging from bacteria to humans. L-Tyrosine participates in a number of enzymatic reactions, within cattle. In particular, L-Tyrosine and oxoglutaric acid can be converted into 4-hydroxyphenylpyruvic acid and L-glutamic acid; which is mediated by the enzyme tyrosine aminotransferase. In addition, L-Tyrosine can be converted into tyramine through its interaction with the enzyme aromatic-L-amino-acid decarboxylase. In cattle, L-tyrosine is involved in a couple of metabolic pathways, which include thyroid hormone synthesis pathway and the tyrosine metabolism pathway. L-Tyrosine is a potentially toxic compound. L-Tyrosine has been found to be associated with several diseases known as irritable bowel syndrome, frontotemporal dementia, obesity, and leukemia; also l-tyrosine has been linked to the inborn metabolic disorders including hypermethioninemia.
Structure
Thumb
Synonyms
ValueSource
(-)-alpha-Amino-p-hydroxyhydrocinnamic acidChEBI
(2S)-2-Amino-3-(4-hydroxyphenyl)propanoic acidChEBI
(S)-(-)-TyrosineChEBI
(S)-2-Amino-3-(p-hydroxyphenyl)propionic acidChEBI
(S)-3-(p-Hydroxyphenyl)alanineChEBI
(S)-alpha-Amino-4-hydroxybenzenepropanoic acidChEBI
(S)-TyrosineChEBI
4-Hydroxy-L-phenylalanineChEBI
L-TyrosinChEBI
TyrChEBI
TYROSINEChEBI
YChEBI
(-)-a-Amino-p-hydroxyhydrocinnamateGenerator
(-)-a-Amino-p-hydroxyhydrocinnamic acidGenerator
(-)-alpha-Amino-p-hydroxyhydrocinnamateGenerator
(-)-Α-amino-p-hydroxyhydrocinnamateGenerator
(-)-Α-amino-p-hydroxyhydrocinnamic acidGenerator
(2S)-2-Amino-3-(4-hydroxyphenyl)propanoateGenerator
(S)-2-Amino-3-(p-hydroxyphenyl)propionateGenerator
(S)-a-Amino-4-hydroxybenzenepropanoateGenerator
(S)-a-Amino-4-hydroxybenzenepropanoic acidGenerator
(S)-alpha-Amino-4-hydroxybenzenepropanoateGenerator
(S)-Α-amino-4-hydroxybenzenepropanoateGenerator
(S)-Α-amino-4-hydroxybenzenepropanoic acidGenerator
(S)-a-Amino-4-hydroxy-benzenepropanoateHMDB
(S)-a-Amino-4-hydroxy-benzenepropanoic acidHMDB
(S)-alpha-Amino-4-hydroxy-benzenepropanoateHMDB
(S)-alpha-Amino-4-hydroxy-benzenepropanoic acidHMDB
2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoateHMDB
2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acidHMDB
3-(4-Hydroxyphenyl)-L-alanineHMDB
BenzenepropanoateHMDB
Benzenepropanoic acidHMDB
L-p-TyrosineHMDB
p-TyrosineHMDB
L TyrosineHMDB
Tyrosine, L-isomerHMDB
Tyrosine, L isomerHMDB
Para tyrosineHMDB
Para-tyrosineHMDB
Chemical FormulaC9H11NO3
Average Molecular Weight181.1885
Monoisotopic Molecular Weight181.073893223
IUPAC Name(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Traditional NameL-tyrosine
CAS Registry Number60-18-4
SMILES
N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
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)/t8-/m0/s1
InChI KeyOUYCCCASQSFEME-QMMMGPOBSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point343 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.48 mg/mLNot Available
LogP-2.26HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-1.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m³·mol⁻¹ChemAxon
Polarizability18.01 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-014i-0690000000-cbbf40bb26fc84f2aead2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-014i-0890000000-ca45f993f95c8b0cee442014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-014i-0890000000-5749069211ba15d713ef2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00xr-9240000000-2c87373c0d964e0edef52014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0890000000-848b2a4f247a0b3f14e82014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00xr-9450000000-6d4550940f4dde6f18ff2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-1910000000-5cc19cad5dc24b3b9b112014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1790000000-de22041357aadf60a06b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0690000000-cbbf40bb26fc84f2aead2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0890000000-ca45f993f95c8b0cee442017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0890000000-5749069211ba15d713ef2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-9240000000-2c87373c0d964e0edef52017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0890000000-848b2a4f247a0b3f14e82017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0udi-3319000000-1d3d28a67f82366fff222017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-9450000000-6d4550940f4dde6f18ff2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1910000000-5cc19cad5dc24b3b9b112017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1790000000-de22041357aadf60a06b2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-4900000000-9be1412408207db5df4e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-9750000000-937b6ee7a745865ee7ee2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01p9-0900000000-580de2c16cd24559cd5c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9400000000-f233fbc6c58236ee4aeb2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002f-9100000000-8b5e12eba034bcfdf8a12012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0920000000-b43356ad3da227b488cb2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-c04f0be6515621dda5ac2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-3ed8b68bfade9194763b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-fe6a1ce69851a8c5db002012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-aafdcea07be221817fd42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-66a5b9a0a48bdc0a2b472012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-13eb4252ca23455a58da2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-fb85798746829bac3f3d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03e9-0839226000-5504e667281c746669ec2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-f65cb3ad2fa730c922f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-a9276fe43ef61b4693e62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a59-0039210000-21b4bd9870bf4965a6d12012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0848491200-aae99eb0b66dd1c7036d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4104a2ca5d5ef5f22f6d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-f309996d57a95c719deb2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0013090000-112cd9c2eea42dbc079b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-c7f95918d936586f633d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03yi-1900000000-d1682546c1e0893c71e42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-2900000000-a0cc78ed35e56dd812a52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00kf-9500000000-d3f399f5dd10e338e25a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9200000000-8acd8d370f194bfe28ed2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-6b26ce2f5b326ace12a42012-08-31View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-7a26097fda66f2f445b52018-05-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified2 - 11 uM details
Detected and Quantified8278 uM details
Detected and Quantified8278 uM details
Detected and Quantified8278 uM details
Detected and Quantified8278 uM details
Detected and Quantified8278 uM details
Detected and Quantified8278 uM details
Detected and Quantified8278 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected and Quantified4 +/- 1 uM details
Detected and Quantified2.6 +/- 0.3 uM details
Detected and Quantified3 +/- 1 uM details
Detected and Quantified4 +/- 1 uM details
Detected and Quantified1.6 +/- 0.1 uM details
Detected and Quantified2.30 +/- 0.04 uM details
Detected and Quantified2.4 +/- 0.1 uM details
Detected and Quantified2.3 +/- 0.1 uM details
Detected and Quantified8 +/- 2 uM details
Detected and Quantified9 +/- 2.51 uM details
Detected and Quantified4 +/- 1 uM details
Detected and Quantified2.6 uM details
Detected and Quantified6 +/- 3 uM details
HMDB IDHMDB0000158
DrugBank IDDB00135
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000446
KNApSAcK IDC00001397
Chemspider ID5833
KEGG Compound IDC00082
BioCyc IDTYR
BiGG ID33785
Wikipedia LinkTyrosine
METLIN ID34
PubChem Compound6057
PDB IDNot Available
ChEBI ID17895
References
Synthesis ReferenceEnei, Hitoshi; Matsui, Hiroshi; Yamashita, Koichi; Okumura, Shinji; Yamada, Hideaki. Microbiological synthesis of L-tyrosine and 3,4-dihydroxyphenyl-L-alanine. I. Distribution of tyrosine phenol lyase in microorganisms. Agricultural and Biological Chemist 1972, 36:11, 1861-1868, DOI: 10.1080/00021369.1972.10860505
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  4. Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug 23. [PubMed:23931703 ]
  5. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  7. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  8. Fooddata+, The Technical University of Denmark (DTU) [Link]