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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 | 2020-04-22 23:33:53 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 is a member of the series of fatty acids found in oils and animal fats. The names of caproic, caprylic, and capric acids are all derived from the word caper (Latin for goat). These fatty acids are light yellowish transparent oily liquids with uncomfortable smells. They are used in organic synthesis, perfume manufacturing, medicine, lubricating grease, rubber, and dye (Chemicalland21). |
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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 | 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 | Not Quantified | Infant (0-1 year old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Available | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Sweat | Detected but not Quantified | Not Quantified | Adult | Both | Normal | | details | | Urine | Detected but not Quantified | 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 | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Metastatic melanoma | | details | | Sweat | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Specified | screen-positive CF | | details | | Urine | Detected but not Quantified | 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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| FooDB 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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| MarkerDB ID | |
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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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