| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:33:00 UTC |
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| Update Date | 2020-06-04 22:28:40 UTC |
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| BMDB ID | BMDB0000573 |
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| Secondary Accession Numbers | - BMDB00573
- BMDB0063575
- BMDB63575
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| Metabolite Identification |
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| Common Name | Elaidic acid |
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| Description | Elaidic acid, also known as (9E)-octadecenoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Elaidic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % of the fatty acids) and some meats. It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid. Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol (Wikipedia). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (9E)-Octadecenoic acid | ChEBI | | (e)-Oleic acid | ChEBI | | 9-OCTADECENOIC ACID | ChEBI | | 9-trans-Octadecenoic acid | ChEBI | | Acide elaidique | ChEBI | | D9-trans-Octadecenoic acid | ChEBI | | Elaidinsaure | ChEBI | | Elaidinsaeure | ChEBI | | trans-9-Octadecenoic acid | ChEBI | | trans-D9-Octadecenoic acid | ChEBI | | trans-Delta(9)-Octadecenoic acid | ChEBI | | trans-Elaidic acid | ChEBI | | trans-Oleic acid | ChEBI | | (9E)-Octadecenoate | Generator | | (e)-Oleate | Generator | | 9-OCTADECENOate | Generator | | 9-trans-Octadecenoate | Generator | | D9-trans-Octadecenoate | Generator | | trans-9-Octadecenoate | Generator | | trans-D9-Octadecenoate | Generator | | trans-delta(9)-Octadecenoate | Generator | | trans-Δ(9)-octadecenoate | Generator | | trans-Δ(9)-octadecenoic acid | Generator | | trans-Elaidate | Generator | | trans-Oleate | Generator | | Elaidate | Generator | | FA(18:1(9E)) | HMDB | | 9-Elaidate | HMDB | | 18:1 N-9 | HMDB | | C18:1 N-9 | HMDB | | Octadec-9-enoic acid | HMDB | | Octadec-9-enoate | HMDB | | 9,10-Octadecenoate | HMDB | | 9,10-Octadecenoic acid | HMDB | | Acid, 9-octadecenoic | HMDB | | 9 Octadecenoic acid | HMDB | | (9E)-9-Octadecenoic acid | HMDB | | (e)-9-Octadecenoic acid | HMDB | | 9-trans-Oleic acid | HMDB | | Elaidinic acid | HMDB | | delta9-trans-Octadecenoic acid | HMDB | | trans-delta9-Octadecenoic acid | HMDB | | trans-Δ9-octadecenoic acid | HMDB | | Δ9-trans-octadecenoic acid | HMDB | | Elaidic acid | KEGG |
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| Chemical Formula | C18H34O2 |
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| Average Molecular Weight | 282.4614 |
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| Monoisotopic Molecular Weight | 282.255880332 |
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| IUPAC Name | (9E)-octadec-9-enoic acid |
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| Traditional Name | elaidic acid |
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| CAS Registry Number | 112-79-8 |
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| SMILES | [H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+ |
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| InChI Key | ZQPPMHVWECSIRJ-MDZDMXLPSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 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 | Long-chain fatty acids |
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| Alternative Parents | |
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| Substituents | - Long-chain 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 | - 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 | 42 - 44 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | 6.78 | Extrapolated |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | |
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| GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00mk-3900000000-26468e9cc1331164ac25 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f6x-9640000000-29b5681d79890854ef2b | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0fe0-9431000000-1879934642ac672cb401 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-001m-9570000000-3794dff1c5c1baa2e7a1 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-4690000000-393df6433d9c0c1e4357 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-07vi-9660000000-38c5c2044b6ae347c0b7 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-0090000000-755e8d1537818580a2fd | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00y0-4690000000-ca39c5846217fe093227 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0596-9830000000-fcb2923d448d11c54559 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-e809fd7222cf63431b77 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001r-1090000000-9c340e3d19cbe7013ccd | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9230000000-6e517cda629fcd4df07d | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-8b8562cadde7e7a8ba4f | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01q9-1090000000-827ccf4b0fb321cd543d | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9220000000-1a90bd2c4041fc8d39eb | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-3290000000-e57551fac255cafaf4fd | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-067j-9410000000-40bef334a898843c3baf | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a5c-9000000000-96ff3dec9c358c726e35 | View in MoNA |
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| MS | Mass Spectrum (Electron Ionization) | splash10-052f-9100000000-350dc6d7ac541a3c5b67 | View in MoNA |
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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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| 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Not Available | View in JSpectraViewer |
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| Biological Properties |
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| Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Biospecimen Locations | - Adipose Tissue
- Blood
- Fibroblasts
- Milk
- Muscle
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected and Quantified | 933.22 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 368.62 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 17763.52 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 6465.31 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 14110.42 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 5799.73 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 8602.95 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 8921.57 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 8468.41 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 8889.71 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 | | Fibroblasts | Expected 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 | 10691.726 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10691.726 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2372.00552 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3681.919 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2372.00552 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 27224.959 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 26198.27 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 26198.27 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | 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 |
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| External Links |
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| HMDB ID | HMDB0000573 |
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| DrugBank ID | DB04224 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB002951 |
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| KNApSAcK ID | C00052377 |
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| Chemspider ID | 553123 |
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| KEGG Compound ID | C01712 |
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| BioCyc ID | Not Available |
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| BiGG ID | 38213 |
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| Wikipedia Link | Elaidic_acid |
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| METLIN ID | 3406 |
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| PubChem Compound | 637517 |
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| PDB ID | Not Available |
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| ChEBI ID | 27997 |
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| References |
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| Synthesis Reference | Vitagliano, Michele. Formation of elaidic acid. Oli, Grassi, Derivati (1967), 111(12), 77-8. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- Lopez C, Briard-Bion V, Menard O, Rousseau F, Pradel P, Besle JM: Phospholipid, sphingolipid, and fatty acid compositions of the milk fat globule membrane are modified by diet. J Agric Food Chem. 2008 Jul 9;56(13):5226-36. doi: 10.1021/jf7036104. Epub 2008 Jun 4. [PubMed:18522410 ]
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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