| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:31:24 UTC |
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| Update Date | 2020-06-04 21:59:04 UTC |
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| BMDB ID | BMDB0000482 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Caprylic acid |
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| Description | Caprylic acid, also known as 8:0 or octylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Caprylic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Caprylic acid exists in all living species, ranging from bacteria to humans. Caprylic acid participates in a number of enzymatic reactions, within cattle. In particular, Caprylic acid can be biosynthesized from trans-2-octenoic acid; which is mediated by the enzyme fatty acid synthase. enoyl reductase domain. In addition, Caprylic acid and malonic acid can be converted into 3-oxodecanoic acid through its interaction with the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, caprylic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Caprylic acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-Heptanecarboxylic acid | ChEBI | | 8:0 | ChEBI | | Acide octanoique | ChEBI | | Acido octanoico | ChEBI | | Acidum octanocium | ChEBI | | Acidum octanoicum | ChEBI | | C8:0 | ChEBI | | CH3-[CH2]6-COOH | ChEBI | | Kaprylsaeure | ChEBI | | N-Caprylic acid | ChEBI | | N-Octanoic acid | ChEBI | | N-Octoic acid | ChEBI | | N-Octylic acid | ChEBI | | OCTANOIC ACID (caprylIC ACID) | ChEBI | | Octansaeure | ChEBI | | Octoic acid | ChEBI | | Octylic acid | ChEBI | | Octanoate | Kegg | | 1-Heptanecarboxylate | Generator | | N-Caprylate | Generator | | N-Octanoate | Generator | | N-Octoate | Generator | | N-Octylate | Generator | | OCTANOate (caprylate) | Generator | | Octoate | Generator | | Octylate | Generator | | Octanoic acid | Generator | | Caprylate | Generator | | Emery 657 | HMDB | | Kortacid 0899 | HMDB | | Lunac 8-95 | HMDB | | Lunac 8-98 | HMDB | | Neo-fat 8 | HMDB | | Neo-fat 8S | HMDB | | Prifac 2901 | HMDB | | Caprylic acid, cadmium salt | HMDB | | Caprylic acid, cesium salt | HMDB | | Caprylic acid, manganese salt | HMDB | | Caprylic acid, nickel(+2) salt | HMDB | | Caprylic acid, zinc salt | HMDB | | Caprylic acid, aluminum salt | HMDB | | Caprylic acid, barium salt | HMDB | | Caprylic acid, chromium(+2) salt | HMDB | | Caprylic acid, lead(+2) salt | HMDB | | Caprylic acid, potassium salt | HMDB | | Caprylic acid, tin(+2) salt | HMDB | | Sodium octanoate | HMDB | | Caprylic acid, 14C-labeled | HMDB | | Caprylic acid, lithium salt | HMDB | | Caprylic acid, ruthenium(+3) salt | HMDB | | Caprylic acid, sodium salt | HMDB | | Caprylic acid, sodium salt, 11C-labeled | HMDB | | Caprylic acid, tin salt | HMDB | | Caprylic acid, zirconium salt | HMDB | | Sodium caprylate | HMDB | | Caprylic acid, ammonia salt | HMDB | | Caprylic acid, calcium salt | HMDB | | Caprylic acid, cobalt salt | HMDB | | Caprylic acid, copper salt | HMDB | | Caprylic acid, copper(+2) salt | HMDB | | Caprylic acid, iridum(+3) salt | HMDB | | Caprylic acid, iron(+3) salt | HMDB | | Caprylic acid, lanthanum(+3) salt | HMDB | | Caprylic acid, zirconium(+4) salt | HMDB | | FA(8:0) | HMDB | | Lithium octanoate | HMDB |
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| Chemical Formula | C8H16O2 |
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| Average Molecular Weight | 144.2114 |
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| Monoisotopic Molecular Weight | 144.115029756 |
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| IUPAC Name | octanoic acid |
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| Traditional Name | caprylic acid |
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| CAS Registry Number | 124-07-2 |
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| SMILES | CCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) |
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| InChI Key | WWZKQHOCKIZLMA-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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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 | Medium-chain fatty acids |
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| Alternative Parents | |
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| Substituents | - Medium-chain fatty acid
- 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
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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 | 16.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.789 mg/mL | Not Available | | LogP | 3.05 | HANSCH,C ET AL. (1995) |
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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 | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Biospecimen Locations | - Blood
- Epidermis
- Milk
- Placenta
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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 | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10.5 +/- 0.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12.92 +/- 6.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13.4 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1594.88 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1386.85 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 277.371 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1317.51 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10.2 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 277.371 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3397.79 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3328.45 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3120.42 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 8.8 +/- 0.1 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 | 16 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 11 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14.11 +/- 1.28 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12.83 +/- 2.57 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.85 +/- 0.77 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.11 +/- 1.026 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12.9 +/- 0.02 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4853.999 +/- 2080.285 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 17.682 +/- 0.42 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 | 23.01 +/- 8.03 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3536.485 +/- 832.114 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3397.799 +/- 693.428 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14.23 +/- 6.69 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.8 (0.6 - 1.6) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.8 (0.6 - 1.4) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.8 (0.6 - 1.7) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.6 (0.8 - 10.6) uM | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000482 |
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| DrugBank ID | DB04519 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB003336 |
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| KNApSAcK ID | C00001231 |
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| Chemspider ID | 370 |
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| KEGG Compound ID | C06423 |
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| BioCyc ID | CPD-195 |
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| BiGG ID | 48223 |
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| Wikipedia Link | Caprylic_acid |
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| METLIN ID | 5469 |
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| PubChem Compound | 379 |
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| PDB ID | Not Available |
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| ChEBI ID | 28837 |
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| References |
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| Synthesis Reference | Caprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp. |
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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 ]
- 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 ]
- GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
- 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 ]
- 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 ]
- 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.
- 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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