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| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:18:50 UTC |
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| Update Date | 2020-06-04 22:16:22 UTC |
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| BMDB ID | BMDB0000039 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Butyric acid |
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| Description | Butyric acid, also known as butyrate or butanoic acid, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Butyric acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Butyric acid exists in all living species, ranging from bacteria to humans. Butyric acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-Butanoic acid | ChEBI | | 1-Butyric acid | ChEBI | | 1-Propanecarboxylic acid | ChEBI | | 4:0 | ChEBI | | Acide butanoique | ChEBI | | Acide butyrique | ChEBI | | Butanic acid | ChEBI | | Butanoate | ChEBI | | Butanoic acid | ChEBI | | Butoic acid | ChEBI | | Buttersaeure | ChEBI | | C4:0 | ChEBI | | CH3-[CH2]2-COOH | ChEBI | | Ethylacetic acid | ChEBI | | N-Butanoic acid | ChEBI | | N-Butyric acid | ChEBI | | Propanecarboxylic acid | ChEBI | | Propylformic acid | ChEBI | | Butyrate | Kegg | | 1-Butanoate | Generator | | 1-Butyrate | Generator | | 1-Propanecarboxylate | Generator | | Butanate | Generator | | Butoate | Generator | | Ethylacetate | Generator | | N-Butanoate | Generator | | N-Butyrate | Generator | | Propanecarboxylate | Generator | | Propylformate | Generator | | Honey robber | HMDB | | Kyselina maselna | HMDB | | Butyrate, magnesium | HMDB | | Magnesium butyrate | HMDB | | Acid, butyric | HMDB | | Butyrate, sodium | HMDB | | Dibutyrate, magnesium | HMDB | | Magnesium dibutyrate | HMDB | | Sodium butyrate | HMDB | | Acid, butanoic | HMDB | | Butyric acid magnesium salt | HMDB | | Butyric acid, sodium salt | HMDB | | FA(4:0) | HMDB | | Butyric acid | KEGG |
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| Chemical Formula | C4H8O2 |
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| Average Molecular Weight | 88.1051 |
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| Monoisotopic Molecular Weight | 88.0524295 |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 107-92-6 |
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| SMILES | Not Available |
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| InChI Identifier | InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) |
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| InChI Key | FERIUCNNQQJTOY-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acids and conjugates |
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| Direct Parent | Straight chain fatty acids |
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| Alternative Parents | |
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| Substituents | - Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -5.7 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 60.0 mg/mL | Not Available | | LogP | 0.79 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | Not Available |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
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| Biospecimen Locations | - Colostrum
- Fibroblasts
- Intestine
- Kidney
- Milk
- Muscle
- Neuron
- Prostate Tissue
- Ruminal Fluid
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| Pathways | |
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| Normal Concentrations |
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| Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 37 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 34.9 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 24 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 27 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 33 +/- 5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 37 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 41 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 52.55 +/- 6.31 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 42 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 56.75 +/- 5.46 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 21.84 +/- 3.36 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 20.16 +/- 5.04 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 46.08 +/- 0.72 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 31780.262 +/- 12485.103 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 44.606 +/- 0.76 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 43.93 +/- 16.09 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 6923.55 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5675.04 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 35.91 +/- 16.47 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1135.00808 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2724.0194 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 17138.641 +/- 2724.0225 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1135.00808 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 16798.139 +/- 2837.523 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13393.0953 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14641.6 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12485.09 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.9 (0.7 - 1.2) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.8 (0.6 - 1.1) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 29.22 +/- 5.72 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.2 (0.8 - 2.4) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.6 (2.4 - 9.6) uM | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 7000-13000 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 10519-17242 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 689 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 642 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 19300 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 7970 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 25848 +/- 9273 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 9386.24 +/- 1366.99 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8100 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8030 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 15130 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 9380 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8100 +/- 1350 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8103 +/- 1631 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 15131 +/- 2957 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 9386 +/- 1367 uM | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Ruminal Fluid | Detected and Quantified | 15131.93 +/- 2863.24 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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| External Links |
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| HMDB ID | HMDB0000039 |
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| DrugBank ID | DB03568 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB031031 |
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| KNApSAcK ID | C00001180 |
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| Chemspider ID | 259 |
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| KEGG Compound ID | C00246 |
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| BioCyc ID | BUTYRIC_ACID |
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| BiGG ID | 34376 |
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| Wikipedia Link | Butyric_acid |
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| METLIN ID | 107 |
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| PubChem Compound | 264 |
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| PDB ID | Not Available |
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| ChEBI ID | 30772 |
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| References |
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| Synthesis Reference | Shan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
- Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
- Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
- Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
- Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
- Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
- 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 ]
- Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]
- van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
- M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
- Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
- 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.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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