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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 | 2020-11-09 23:14:45 UTC |
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HMDB ID | HMDB0000827 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Stearic acid |
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Description | Stearic acid, also known as stearate or 18:0, 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. Stearic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Stearic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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18:0 | ChEBI | Acide octadecanoique | ChEBI | Acide stearique | ChEBI | C18:0 | ChEBI | CH3-[CH2]16-COOH | ChEBI | N-Octadecanoic acid | ChEBI | Octadecansaeure | ChEBI | Octadecoic acid | ChEBI | Oktadekansaeure | ChEBI | Stearinsaeure | ChEBI | Stearate | Kegg | N-Octadecanoate | Generator | Octadecoate | Generator | Octadecanoic acid | HMDB | Octadecanoate | HMDB | 1-Heptadecanecarboxylate | HMDB | 1-Heptadecanecarboxylic acid | HMDB | Stearex beads | HMDB | Stearic acid cherry | HMDB | Stearophanate | HMDB | Stearophanic acid | HMDB | Calcium stearate | HMDB | Aluminum tristearate | HMDB | Ammonium stearate | HMDB | Zinc stearate | HMDB | Magnesium stearate | HMDB | Sodium stearate | HMDB | Aluminum monostearate | HMDB | FA(18:0) | HMDB |
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Chemical Formula | C18H36O2 |
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Average Molecular Weight | 284.4772 |
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Monoisotopic Molecular Weight | 284.271530396 |
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IUPAC Name | octadecanoic acid |
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Traditional Name | stearic acid |
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CAS Registry Number | 57-11-4 |
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SMILES | CCCCCCCCCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) |
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InChI Key | QIQXTHQIDYTFRH-UHFFFAOYSA-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
- 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 | 68.8 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0006 mg/mL | Not Available | LogP | 8.23 | SANGSTER (1993) |
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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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-0159-1900000000-9cc966384906cd35537d | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0159-0900000000-b87a9955374d11966ba6 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-0100-9700000000-979da356343fa0697993 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0159-2901000000-16194c704b7abd193647 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-06yo-9110000000-6f345827577cdc861aca | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-075c-9220000000-207b53a511763954eb66 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-1900000000-9cc966384906cd35537d | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0900000000-b87a9955374d11966ba6 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0100-9700000000-979da356343fa0697993 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0159-2901000000-16194c704b7abd193647 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-1900000000-d34fc01a79cc27a32080 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9540000000-c6c002443ac3a40dabdb | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-009l-9551000000-b9a196da32e6273fad4f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-001i-0090000000-1368043827a20e28c172 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-001i-0090000000-5c3fa1d38cf3d0a38d74 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004r-0791000000-10ab351997f48e512657 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-004r-0791000000-10ab351997f48e512657 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004r-0791000000-10ab351997f48e512657 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-001i-0090000000-55efcdc9c7bfd521ef5a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-001i-0090000000-9441e6362046ae198384 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-001i-0090000000-f629b105972a0728beb6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-001i-0090000000-fbf3f8e91badb0ec251d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-001i-0090000000-55efcdc9c7bfd521ef5a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-00lr-0090000000-a702a9f469dbb513856a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-001i-0090000000-9441e6362046ae198384 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-001i-0090000000-fbf3f8e91badb0ec251d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0090000000-34a309d09cb2def46a19 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-4690000000-f68e827f7ebccd80d5bf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-8920000000-2e865f09d760af582c07 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0090000000-34a309d09cb2def46a19 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-4690000000-f68e827f7ebccd80d5bf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-8920000000-2e865f09d760af582c07 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-b3ce35f839a30b41c718 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9240000000-1b84b49819fa37fce1ae | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-b3ce35f839a30b41c718 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9240000000-1b84b49819fa37fce1ae | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0c03-9200000000-5dd52f837d56d80fa968 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | 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 | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Sweat
- Urine
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Tissue Locations | - Adipose Tissue
- Brain
- Epidermis
- Erythrocyte
- Fibroblasts
- Intestine
- Neuron
- Placenta
- Platelet
- Prostate
- Skeletal Muscle
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 85 (31-470) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 48.8 +/- 21 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 41.119 +/- 5.521 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 7.90-13.5 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 8.70-13.3 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 467.524 +/- 38.667 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 460.494 +/- 31.637 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 460.494 +/- 35.152 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 464.00907 +/- 35.152 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 57 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 60 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 73 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 78 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 232 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 261 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 707.790 +/- 164.407 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 585.741 +/- 101.871 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 830 +/- 160 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 770 +/- 110 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 22.1 +/- 0.035 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 10.0 +/- 10.0 uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | 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 | Children (1-13 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 | Not Specified | Not Specified | Normal | | details | Feces | Detected and Quantified | 71.429 +/- 129.114 nmol/g wet feces | Not Specified | 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 and Quantified | 44.995 +/- 75.226 nmol/g wet feces | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 6.88 +/- 1.23 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | 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) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Sweat | Detected but not Quantified | Not Quantified | Adult | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 3.36 +/- 2.82 umol/mmol creatinine | Adult (>18 years old) | Both | Not Available | | details | Urine | Detected and Quantified | 18.703 +/- 7.698 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 | Urine | Detected and Quantified | 0.32-0.82 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 2.9 (1.6-6.6) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.10 +/- 0.03 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0-4.1 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | Urine | Detected and Quantified | 0-6.5 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | Urine | Detected and Quantified | 0-6.61 umol/mmol creatinine | Infant (0-1 year old) | Female | Normal | | details | Urine | Detected and Quantified | 0-9.75 umol/mmol creatinine | Infant (0-1 year old) | Female | Normal | | details | Urine | Detected and Quantified | 0.35-0.50 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 3.9(2.3-7.7) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Schizophrenia | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Schizophrenia | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Breast 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 | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Iron deficiency | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | CCD | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ileal Crohn's disease | | 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 | Urine | Detected and Quantified | 26.428 +/- 22.351 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 33.059 +/- 25.405 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Perillyl alcohol administration for cancer treatment |
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- Lv W, Yang T: Identification of possible biomarkers for breast cancer from free fatty acid profiles determined by GC-MS and multivariate statistical analysis. Clin Biochem. 2012 Jan;45(1-2):127-33. doi: 10.1016/j.clinbiochem.2011.10.011. Epub 2011 Oct 26. [PubMed:22061338 ]
| Schizophrenia |
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- Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
- Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
| Crohn's disease |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
| Iron deficiency |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
| 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 ]
| 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 | DB03193 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031183 |
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KNApSAcK ID | C00001238 |
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Chemspider ID | 5091 |
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KEGG Compound ID | C01530 |
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BioCyc ID | STEARIC_ACID |
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BiGG ID | 37799 |
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Wikipedia Link | Stearic_acid |
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METLIN ID | 189 |
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PubChem Compound | 5281 |
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PDB ID | Not Available |
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ChEBI ID | 28842 |
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Food Biomarker Ontology | Not Available |
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VMH ID | OCDCA |
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MarkerDB ID | MDB00000263 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. [PubMed:15854043 ]
- Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. [PubMed:10391868 ]
- Sanjurjo P, Rodriguez-Alarcon J, Rodriguez-Soriano J: Plasma fatty acid composition during the first week of life following feeding with human milk or formula. Acta Paediatr Scand. 1988 Mar;77(2):202-6. [PubMed:3354331 ]
- Neoptolemos JP, Thomas BS: Erythrocyte membrane stearic acid: oleic acid ratios in colorectal cancer using tube capillary column gas liquid chromatography. Ann Clin Biochem. 1990 Jan;27 ( Pt 1):38-43. [PubMed:2310156 ]
- Turpeinen AM, Wubert J, Aro A, Lorenz R, Mutanen M: Similar effects of diets rich in stearic acid or trans-fatty acids on platelet function and endothelial prostacyclin production in humans. Arterioscler Thromb Vasc Biol. 1998 Feb;18(2):316-22. [PubMed:9484999 ]
- Daubresse JC: [Atherosclerosis and nutrition]. Rev Med Brux. 2000 Sep;21(4):A359-62. [PubMed:11068494 ]
- Hoppu U, Rinne M, Lampi AM, Isolauri E: Breast milk fatty acid composition is associated with development of atopic dermatitis in the infant. J Pediatr Gastroenterol Nutr. 2005 Sep;41(3):335-8. [PubMed:16131990 ]
- Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
- Musial W, Kubis A: Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum. Eur J Pharm Biopharm. 2003 Mar;55(2):237-40. [PubMed:12637103 ]
- Doran TA, Ford JA, Allen LC, Wong PY, Benzie RJ: Amniotic fluid lecithin/sphingomyelin ratio, palmitic acid, palmitic acid/stearic acid ratio, total cortisol, creatinine, and percentage of lipid-positive cells in assessment of fetal maturity and fetal pulmonary maturity: a comparison. Am J Obstet Gynecol. 1979 Feb 1;133(3):302-7. [PubMed:433991 ]
- Kazmierczak SC, Gurachevsky A, Matthes G, Muravsky V: Electron spin resonance spectroscopy of serum albumin: a novel new test for cancer diagnosis and monitoring. Clin Chem. 2006 Nov;52(11):2129-34. Epub 2006 Sep 21. [PubMed:16990414 ]
- Kelly FD, Sinclair AJ, Mann NJ, Turner AH, Abedin L, Li D: A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. Eur J Clin Nutr. 2001 Feb;55(2):88-96. [PubMed:11305631 ]
- Diani F, Cacco M, Molinaroli A, Cerruti G, Meloncelli C, Turinetto A: [Fatty acid composition of the cervical mucus obtained during ovulation and at the term of pregnancy]. Minerva Ginecol. 1998 Oct;50(10):405-10. [PubMed:9866950 ]
- 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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