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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-02-26 21:22:16 UTC |
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| HMDB ID | HMDB0000511 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Capric acid |
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| Description | Capric acid, also known as decanoate or 10:0, 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. Capric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Capric acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-Nonanecarboxylic acid | ChEBI | | 10:0 | ChEBI | | C10:0 | ChEBI | | Caprinic acid | ChEBI | | CH3-[CH2]8-COOH | ChEBI | | Decanoate | ChEBI | | Decoic acid | ChEBI | | Decylic acid | ChEBI | | Dekansaeure | ChEBI | | Kaprinsaeure | ChEBI | | N-Capric acid | ChEBI | | N-Decanoic acid | ChEBI | | N-Decoic acid | ChEBI | | N-Decylic acid | ChEBI | | 1-Nonanecarboxylate | Generator | | Caprinate | Generator | | Decanoic acid | Generator | | Decoate | Generator | | Decylate | Generator | | N-Caprate | Generator | | N-Decanoate | Generator | | N-Decoate | Generator | | N-Decylate | Generator | | Caprate | Generator | | Caprynate | HMDB | | Caprynic acid | HMDB | | Emery 659 | HMDB | | Lunac 10-95 | HMDB | | Lunac 10-98 | HMDB | | Prifac 2906 | HMDB | | Prifac 296 | HMDB | | Decanoic acid, sodium salt | HMDB | | Sodium caprate | HMDB | | Sodium decanoate | HMDB | | FA(10:0) | HMDB |
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| Chemical Formula | C10H20O2 |
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| Average Molecular Weight | 172.2646 |
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| Monoisotopic Molecular Weight | 172.146329884 |
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| IUPAC Name | decanoic acid |
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| Traditional Name | capric acid |
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| CAS Registry Number | 334-48-5 |
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| SMILES | CCCCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) |
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| InChI Key | GHVNFZFCNZKVNT-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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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Biological role: Industrial application: |
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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 | 31.9 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.062 mg/mL | Not Available | | LogP | 4.09 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-017i-2920000000-7f6721f01b80a790d544 | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-076u-9000000000-96a2e9e00e464db3c086 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-017i-2920000000-7f6721f01b80a790d544 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-016r-1910000000-1cc1026f6f325d994ab4 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-052g-9200000000-71a57b0e200e46fb66ed | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00g0-9300000000-c615f39c0b907a00f67c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-0900000000-771e7907916bf05e6b10 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00di-0900000000-f1e000384728ee06f802 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-1900000000-42a901bb54546da030da | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-9000000000-83e77de04461ded1c4bc | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9000000000-f3190b828218d04d3cc7 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-014i-0000000910-e82208ed71b4a3735258 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-00di-0900000000-6ec01ce9b8fdc68d94a9 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-00di-0900000000-6ec01ce9b8fdc68d94a9 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-00di-0900000000-8c6cdf0491f51ba6ef26 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-00di-0900000000-6ec01ce9b8fdc68d94a9 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-00di-0900000000-3afa642872e4450f0c49 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-0900000000-771e7907916bf05e6b10 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-0900000000-f1e000384728ee06f802 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-1900000000-d5dbc60c65c1a7d34e2f | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-83e77de04461ded1c4bc | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-f3190b828218d04d3cc7 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-00di-0900000000-53ea38eb25eaea66d22a | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00di-0900000000-8c6cdf0491f51ba6ef26 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00di-0900000000-3afa642872e4450f0c49 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-0900000000-0a7f944302bce161f7e5 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00b9-1900000000-b68efbceecf3433a9995 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-005a-9600000000-f2a54ed1a56ee9b7af77 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-076u-9000000000-96a2e9e00e464db3c086 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-00kf-0900100000-28cc3e7dc24d4208e159 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-0900000000-3eb3455ff5fbfa8a3a2c | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-074l-9100000000-bf788cb34c09c6af56bf | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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| Biospecimen Locations | - Blood
- Breast Milk
- Feces
- Saliva
- Sweat
- Urine
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 11.0 (5.0-17.0) uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected but not Quantified | | Adult (>18 years old) | Female | Normal | | details | | Breast Milk | Detected and Quantified | 53.7 +/- 19.3 uM | Adult (>18 years old) | Female | Normal | | details | | Feces | Detected but not Quantified | | Infant (0-1 year old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Infant (0-1 year old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Infant (0-1 year old) | Not Available | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Sweat | Detected but not Quantified | | Adult | Both | Normal | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 10.607 +/- 3.815 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Metastatic melanoma | | details | | Sweat | Detected but not Quantified | | Infant (0-1 year old) | Not Specified | screen-positive CF | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Breast cancer | | details | | Urine | Detected and Quantified | 9.517 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| | Metastatic melanoma |
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- Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
| | Cystic fibrosis |
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- Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
| | Perillyl alcohol administration for cancer treatment |
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- Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
| | Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | DB03600 |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB012027 |
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| KNApSAcK ID | C00001213 |
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| Chemspider ID | 2863 |
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| KEGG Compound ID | C01571 |
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| BioCyc ID | CPD-3617 |
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| BiGG ID | Not Available |
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| Wikipedia Link | Decanoic acid |
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| METLIN ID | 336 |
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| PubChem Compound | 2969 |
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| PDB ID | Not Available |
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| ChEBI ID | 30813 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | DCA |
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| References |
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| Synthesis Reference | Wang, Qin; Ni, Xindi; Shi, Jianying. Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil. Huaxue Shijie (1993), 34(2), 84-7. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Farrington CJ, Chalmers AH: Gas-chromatographic estimation of urinary oxalate and its comparison with a colorimetric method. Clin Chem. 1979 Dec;25(12):1993-6. [PubMed:509698 ]
- Lima TM, Kanunfre CC, Pompeia C, Verlengia R, Curi R: Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis. Toxicol In Vitro. 2002 Dec;16(6):741-7. [PubMed:12423658 ]
- Wanten GJ, Janssen FP, Naber AH: Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length. Eur J Clin Invest. 2002 Apr;32(4):285-9. [PubMed:11952815 ]
- Lindmark T, Kimura Y, Artursson P: Absorption enhancement through intracellular regulation of tight junction permeability by medium chain fatty acids in Caco-2 cells. J Pharmacol Exp Ther. 1998 Jan;284(1):362-9. [PubMed:9435199 ]
- Kaiya H, Van Der Geyten S, Kojima M, Hosoda H, Kitajima Y, Matsumoto M, Geelissen S, Darras VM, Kangawa K: Chicken ghrelin: purification, cDNA cloning, and biological activity. Endocrinology. 2002 Sep;143(9):3454-63. [PubMed:12193558 ]
- Eriksson T, Bjorkman S, Roth B, Fyge A, Hoglund P: Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis. Chirality. 1998;10(3):223-8. [PubMed:9499573 ]
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Da Silva MA, Medeiros VC, Langone MA, Freire DM: Synthesis of monocaprin catalyzed by lipase. Appl Biochem Biotechnol. 2003 Spring;105 -108:757-67. [PubMed:12721413 ]
- Imai T, Sakai M, Ohtake H, Azuma H, Otagiri M: Absorption-enhancing effect of glycyrrhizin induced in the presence of capric acid. Int J Pharm. 2005 Apr 27;294(1-2):11-21. [PubMed:15814227 ]
- Leopold CS, Lippold BC: An attempt to clarify the mechanism of the penetration enhancing effects of lipophilic vehicles with differential scanning calorimetry (DSC). J Pharm Pharmacol. 1995 Apr;47(4):276-81. [PubMed:7791023 ]
- Saso L, Valentini G, Grippa E, Leone MG, Silvestrini B: Effect of selected substances on heat-induced aggregation of albumin, IgG and lysozyme. Res Commun Mol Pathol Pharmacol. 1998 Oct;102(1):15-28. [PubMed:9920343 ]
- Kaiya H, Kojima M, Hosoda H, Riley LG, Hirano T, Grau EG, Kangawa K: Identification of tilapia ghrelin and its effects on growth hormone and prolactin release in the tilapia, Oreochromis mossambicus. Comp Biochem Physiol B Biochem Mol Biol. 2003 Jul;135(3):421-9. [PubMed:12831762 ]
- Coyne CB, Ribeiro CM, Boucher RC, Johnson LG: Acute mechanism of medium chain fatty acid-induced enhancement of airway epithelial permeability. J Pharmacol Exp Ther. 2003 May;305(2):440-50. Epub 2003 Feb 11. [PubMed:12606647 ]
- Tanaka S, Saitoh O, Tabata K, Matsuse R, Kojima K, Sugi K, Nakagawa K, Kayazawa M, Teranishi T, Uchida K, Hirata I, Katsu K: Medium-chain fatty acids stimulate interleukin-8 production in Caco-2 cells with different mechanisms from long-chain fatty acids. J Gastroenterol Hepatol. 2001 Jul;16(7):748-54. [PubMed:11446882 ]
- Duran M, Mitchell G, de Klerk JB, de Jager JP, Hofkamp M, Bruinvis L, Ketting D, Saudubray JM, Wadman SK: Octanoic acidemia and octanoylcarnitine excretion with dicarboxylic aciduria due to defective oxidation of medium-chain fatty acids. J Pediatr. 1985 Sep;107(3):397-404. [PubMed:4032135 ]
- Wallon C, Braaf Y, Wolving M, Olaison G, Soderholm JD: Endoscopic biopsies in Ussing chambers evaluated for studies of macromolecular permeability in the human colon. Scand J Gastroenterol. 2005 May;40(5):586-95. [PubMed:16036512 ]
- Van Immerseel F, De Buck J, Boyen F, Bohez L, Pasmans F, Volf J, Sevcik M, Rychlik I, Haesebrouck F, Ducatelle R: Medium-chain fatty acids decrease colonization and invasion through hilA suppression shortly after infection of chickens with Salmonella enterica serovar Enteritidis. Appl Environ Microbiol. 2004 Jun;70(6):3582-7. [PubMed:15184160 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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