Record Information |
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Version | 5.0 |
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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 | 2022-03-07 02:49:01 UTC |
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HMDB ID | HMDB0000394 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Hydroxytetradecanedioic acid |
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Description | 3-Hydroxytetradecanedioic acid is an unusual 3-hydroxydicarboxylic acid human metabolite found occasionally in urine. (PMID 2925825 ) High levels of 3-Hydroxytetradecanedioic acid (and other 3-hydroxydicarboxylic acids) were detected in the urine of a patient with 3-hydroxydicarboxylic aciduria (PMID 1507493 ), due to acute intoxication associated with hopantenate occurs owing to pantothenic acid deficiency or the inhibition of CoA-requiring reactions during stress, i.e., infection, prolonged fasting, or malnutrition (PMID 2026687 ), and in a patient with thanatophoric dysplasia due to enhanced but incomplete oxidation of fatty acid, a consequence of a heterozygous point mutation, S249C in the fibroblast growth factor receptor 3 gene. (PMID 11879084 ). |
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Structure | OC(CCCCCCCCCCC(O)=O)CC(O)=O InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19) |
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Synonyms | Value | Source |
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3-Hydroxytetradecanedioate | Generator | 3-Hydroxy-tetradecanedioate | HMDB |
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Chemical Formula | C14H26O5 |
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Average Molecular Weight | 274.3532 |
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Monoisotopic Molecular Weight | 274.178023942 |
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IUPAC Name | 3-hydroxytetradecanedioic acid |
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Traditional Name | 3-hydroxytetradecanedioic acid |
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CAS Registry Number | 73179-89-2 |
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SMILES | OC(CCCCCCCCCCC(O)=O)CC(O)=O |
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InChI Identifier | InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19) |
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InChI Key | CEDZIURHISELSQ-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
- Hydroxy fatty acid
- Beta-hydroxy acid
- Hydroxy acid
- Dicarboxylic acid or derivatives
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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3-Hydroxytetradecanedioic acid,1TMS,isomer #1 | C[Si](C)(C)OC(CCCCCCCCCCC(=O)O)CC(=O)O | 2345.1 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O | 2373.1 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,1TMS,isomer #3 | C[Si](C)(C)OC(=O)CC(O)CCCCCCCCCCC(=O)O | 2360.1 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C | 2384.0 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)CC(CCCCCCCCCCC(=O)O)O[Si](C)(C)C | 2370.6 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,2TMS,isomer #3 | C[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C | 2431.6 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2445.5 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(CCCCCCCCCCC(=O)O)CC(=O)O | 2604.5 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O | 2629.9 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CC(O)CCCCCCCCCCC(=O)O | 2616.5 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C(C)(C)C | 2921.0 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CC(CCCCCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2881.2 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C(C)(C)C | 2912.3 | Semi standard non polar | 33892256 | 3-Hydroxytetradecanedioic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3153.1 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9670000000-59c708cd80a1a877c79d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (3 TMS) - 70eV, Positive | splash10-004i-9367800000-47e5a2287d205a6fa02b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxytetradecanedioic acid GC-MS (TBDMS_3_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 10V, Positive-QTOF | splash10-0a70-0090000000-d1bf3dd36ae3dbdb5185 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Positive-QTOF | splash10-08i9-0490000000-31021daf233368701f5c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Positive-QTOF | splash10-040d-4910000000-e13f32a9e5177e2e956f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 10V, Negative-QTOF | splash10-00di-0090000000-a11f84f48743557a02ab | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Negative-QTOF | splash10-0729-1190000000-d4f10462ec57b05c5171 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Negative-QTOF | splash10-0a4l-9330000000-d55db446d3aebb26fa93 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 10V, Negative-QTOF | splash10-00di-0090000000-265d760b412867c1fc5b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Negative-QTOF | splash10-0ab9-4290000000-e6a2a92e8d6e8157fb33 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Negative-QTOF | splash10-0a4i-9230000000-71bfc30db58564285713 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 10V, Positive-QTOF | splash10-056r-1290000000-112d6e8e034b7c4a28a8 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 20V, Positive-QTOF | splash10-0avi-9520000000-49001720daac9e4dd43a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanedioic acid 40V, Positive-QTOF | splash10-0a59-9000000000-01b43981d92af775a9ff | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.21(0.068-0.54) uM | Infant (0-1 year old) | Not Specified | Normal | | details | Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.90-17.6 uM uM | Infant (0-1 year old) | Female | 3-Hydroxydicarboxylic aciduria | | details | Urine | Detected but not Quantified | Not Quantified | Not Available | Not Available | Ketosis | | details | Urine | Detected but not Quantified | Not Quantified | Not Available | Not Available | CHAD/TFP deficiency | | details | Urine | Detected but not Quantified | Not Quantified | Not Available | Not Available | Hepatocellular disease | | details |
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Associated Disorders and Diseases |
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Disease References | Ketosis |
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- Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022012 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 13628077 |
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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 | Not Available |
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METLIN ID | 5383 |
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PubChem Compound | 20848956 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Hill, Frank Friedrich. Manufacture of 3-hydroxydicarboxylic acids. Ger. Offen. (1986), 14 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Lefevere MF, Verhaeghe BJ, Declerck DH, Van Bocxlaer JF, De Leenheer AP, De Sagher RM: Metabolic profiling of urinary organic acids by single and multicolumn capillary gas chromatography. J Chromatogr Sci. 1989 Jan;27(1):23-9. [PubMed:2925825 ]
- Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I: Abnormal fatty acid metabolism in patients in hopantenate therapy during clinical episodes. J Chromatogr. 1991 Jan 2;562(1-2):139-45. [PubMed:2026687 ]
- Okajima K, Asai K, Niwa T, Ohki S, Sobajima H, Tyson J, Malcolm S, Wada Y: Clinical and biochemical findings of a patient with thanatophoric dysplasia type I: additional finding of dicarboxylic aciduria. Cleft Palate Craniofac J. 2002 Mar;39(2):246-8. [PubMed:11879084 ]
- Shimizu A, Nakanishi T: [Quantitative analysis of urinary organic acid]. Rinsho Byori. 1992 Jul;40(7):743-50. [PubMed:1507493 ]
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