| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:29:14 UTC |
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| Update Date | 2020-06-04 20:35:41 UTC |
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| BMDB ID | BMDB0000357 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 3-Hydroxybutyric acid |
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| Description | 3-Hydroxybutyric acid, also known as 3-hydroxybutyrate or 3-hydroxybuttersaeure, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 3-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 3-Hydroxybutyric acid is a potentially toxic compound. 3-Hydroxybutyric acid has been found to be associated with several diseases known as pyruvate dehydrogenase phosphatase deficiency, schizophrenia, adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency, and colorectal cancer; also 3-hydroxybutyric acid has been linked to the inborn metabolic disorders including medium chain acyl-coa dehydrogenase deficiency. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (1)-3-Hydroxybutyric acid | ChEBI | | 3 HBA | ChEBI | | 3-Hydroxybuttersaeure | ChEBI | | 3-OH-Butyric acid | ChEBI | | beta-Hydroxy-N-butyric acid | ChEBI | | beta-Hydroxybutanoic acid | ChEBI | | beta-Hydroxybuttersaeure | ChEBI | | beta-Hydroxybutyric acid | ChEBI | | BHBA | ChEBI | | DL-beta-Hydroxybutyric acid | ChEBI | | (1)-3-Hydroxybutyrate | Generator | | 3-OH-Butyrate | Generator | | b-Hydroxy-N-butyrate | Generator | | b-Hydroxy-N-butyric acid | Generator | | beta-Hydroxy-N-butyrate | Generator | | Β-hydroxy-N-butyrate | Generator | | Β-hydroxy-N-butyric acid | Generator | | b-Hydroxybutanoate | Generator | | b-Hydroxybutanoic acid | Generator | | beta-Hydroxybutanoate | Generator | | Β-hydroxybutanoate | Generator | | Β-hydroxybutanoic acid | Generator | | b-Hydroxybuttersaeure | Generator | | Β-hydroxybuttersaeure | Generator | | b-Hydroxybutyrate | Generator | | b-Hydroxybutyric acid | Generator | | beta-Hydroxybutyrate | Generator | | Β-hydroxybutyrate | Generator | | Β-hydroxybutyric acid | Generator | | DL-b-Hydroxybutyrate | Generator | | DL-b-Hydroxybutyric acid | Generator | | DL-beta-Hydroxybutyrate | Generator | | DL-Β-hydroxybutyrate | Generator | | DL-Β-hydroxybutyric acid | Generator | | 3-Hydroxybutyrate | Generator | | 3-Hydroxy-butanoate | HMDB | | 3-Hydroxy-butanoic acid | HMDB | | 3-Hydroxy-butyrate | HMDB | | 3-Hydroxy-butyric acid | HMDB | | 3-Hydroxybutanoate | HMDB | | 3-Hydroxybutanoic acid | HMDB | | Biopol | HMDB | | DL-3-Hydroxybutyrate | HMDB | | DL-3-Hydroxybutyric acid | HMDB | | beta Hydroxybutyric acid | HMDB | | 3 Hydroxybutyric acid | HMDB | | beta Hydroxybutyrate | HMDB | | (+ -)-3-Hydroxybutyric acid | HMDB | | 3 Hydroxybutyrate | HMDB |
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| Chemical Formula | C4H8O3 |
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| Average Molecular Weight | 104.1045 |
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| Monoisotopic Molecular Weight | 104.047344122 |
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| IUPAC Name | 3-hydroxybutanoic acid |
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| Traditional Name | 3 hydroxybutyrate |
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| CAS Registry Number | 300-85-6 |
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| SMILES | CC(O)CC(O)=O |
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| InChI Identifier | InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) |
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| InChI Key | WHBMMWSBFZVSSR-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Hydroxy acids and derivatives |
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| Sub Class | Beta hydroxy acids and derivatives |
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| Direct Parent | Beta hydroxy acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Short-chain hydroxy acid
- Beta-hydroxy acid
- Fatty acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 46 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 444 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Blood
- Brain
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Neuron
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 500 +/- 30 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 4547 +/- 1058 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 340 +/- 145 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 660-950 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 600-740 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 250-2110 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 355 +/- 89 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 97 +/- 27 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 34.06 +/- 10.63 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 110 +/- 20 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10 - 631 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 26 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 29 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 26 +/- 5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 30 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10 - 531 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12 - 121 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 and Quantified | 69 +/- 7 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 | 28.18 +/- 2.92 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 24.63 +/- 4.75 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 114-242 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1260 +/- 420 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1470 +/- 390 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 860 +/- 180 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 940 +/- 260 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | Expected 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 | | Semimembranosus Muscle | Detected and Quantified | 88 +/- 33 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 101 +/- 23 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | | Blood | Detected and Quantified | 1550 +/- 170 uM | Not Specified | Not Specified | Left displaced abomasum (LDA) | | details | | Blood | Detected and Quantified | 640 +/- 90 uM | Not Specified | Not Specified | Right displaced abomasum (RDA) | | details | | Blood | Detected and Quantified | 8042 +/- 1256 uM | Not Specified | Not Specified | Left displaced abomasum (LDA) | | details | | Blood | Detected and Quantified | 2970 +/- 784 uM | Not Specified | Not Specified | Right displaced abomasum (RDA) | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details |
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| External Links |
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| HMDB ID | HMDB0000357 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB021797 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 428 |
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| KEGG Compound ID | C01089 |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | 3-hydroxybutyrate |
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| METLIN ID | 125 |
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| PubChem Compound | 441 |
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| PDB ID | Not Available |
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| ChEBI ID | 20067 |
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| References |
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| Synthesis Reference | Yang, Wenling; Ma, Peisheng; Wang, Jianing; Wang, Chunfang; Li, Haixia. Study on the process of chemical synthesis of 3-hydroxybutyric acid. Huaxue Gongcheng (Xi'an, China) (2002), 30(5), 74-78. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0. [PubMed:11286410 ]
- Nielsen NI, Ingvartsen KL, Larsen T: Diurnal variation and the effect of feed restriction on plasma and milk metabolites in TMR-fed dairy cows. J Vet Med A Physiol Pathol Clin Med. 2003 Mar;50(2):88-97. [PubMed:12667199 ]
- Larsen T, Nielsen NI: Fluorometric determination of beta-hydroxybutyrate in milk and blood plasma. J Dairy Sci. 2005 Jun;88(6):2004-9. doi: 10.3168/jds.S0022-0302(05)72876-9. [PubMed:15905430 ]
- 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 ]
- Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- 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 ]
- 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 ]
- Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
- Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
- 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 ]
- 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.
- 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.
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