| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:45:14 UTC |
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| Update Date | 2020-06-04 22:39:53 UTC |
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| BMDB ID | BMDB0001388 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Alpha-Linolenic acid |
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| Description | Alpha-Linolenic acid, also known as A-linolenate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Alpha-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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| Structure | |
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| Synonyms | | Value | Source |
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| a-Linolenate | Generator | | a-Linolenic acid | Generator | | alpha-Linolenate | Generator | | Α-linolenate | Generator | | Α-linolenic acid | Generator | | Elaidolinolenate | Generator |
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| Chemical Formula | C18H30O2 |
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| Average Molecular Weight | 278.436 |
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| Monoisotopic Molecular Weight | 278.224580206 |
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| IUPAC Name | (9E,12E,15E)-octadeca-9,12,15-trienoic acid |
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| Traditional Name | elaidolinoleic acid |
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| CAS Registry Number | Not Available |
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| SMILES | [H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+ |
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| InChI Key | DTOSIQBPPRVQHS-IUQGRGSQSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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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 | Lineolic acids and derivatives |
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| Direct Parent | Lineolic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Octadecanoid
- Long-chain fatty acid
- Fatty acid
- Unsaturated 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 | - 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 | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | 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 | - Cell membrane
- Cytoplasm
- Membrane
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| Biospecimen Locations | - Adipose Tissue
- Epidermis
- Fibroblasts
- Intestine
- Liver
- Milk
- Muscle
- Oocyte
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected and Quantified | 3763.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1338.33 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 40120.75 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 0 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 34354.61 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 16474.0192 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 7434.38 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 8404.09 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 8260.43 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 9018.23 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | 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 | | 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 | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3591.49 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3950.639 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4668.936 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.78 +/- 0.22 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 71.83 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 71.83 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 71.83 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 933.787 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.8 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 6.01 +/- 0.03 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 6.4 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 7.44 +/- 0.53 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.52 +/- 0.53 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.39 +/- 0.53 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 6.36 +/- 0.09 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1077.470 +/- 359.157 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 | 1221.133 +/- 502.819 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 933.807 +/- 466.904 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1041.554 +/- 359.157 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 790.145 +/- 323.241 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Oocyte | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | 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 | 0.5 +/- 0.4 uM | 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 | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Alpha-Linolenic acid |
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| METLIN ID | Not Available |
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| PubChem Compound | 5282822 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| Synthesis Reference | Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15. |
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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 ]
- 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 ]
- Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
- 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 ]
- Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
- 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.
- M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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