Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:58 UTC |
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Update date | 2019-11-26 03:09:15 UTC |
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Primary ID | FDB013897 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Hexanoic acid |
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Description | Present in apple, wine grapes, butter, licorice and cheeses, e.g. blue cheeses, Cheddar cheese, Swiss cheese, feta cheese, gruyere de comte cheese, etcand is) also present in a few essential oils and fruital aromas. Secondary product of butyric acid fermentation. Flavouring ingredient
Hexanoic acid (common name caproic acid), is the carboxylic acid derived from hexane with the general formula C5H11COOH. It is a colorless oily liquid with an odor reminiscent of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. Hexanoic acid is found in many foods, some of which are tapioca pearl, meat bouillon, pecan nut, and oval-leaf huckleberry. |
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CAS Number | 142-62-1 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Hexanoic acid | ChEBI | 1-Pentanecarboxylic acid | ChEBI | 6:0 | ChEBI | Butylacetic acid | ChEBI | C6:0 | ChEBI | Capronic acid | ChEBI | CH3-[CH2]4-COOH | ChEBI | Hexanoate | ChEBI | Hexoic acid | ChEBI | Hexylic acid | ChEBI | N-Caproic acid | ChEBI | N-Hexanoic acid | ChEBI | N-Hexoic acid | ChEBI | N-Hexylic acid | ChEBI | Pentanecarboxylic acid | ChEBI | Pentiformic acid | ChEBI | Pentylformic acid | ChEBI | 1-Hexanoate | Generator | 1-Pentanecarboxylate | Generator | Butylacetate | Generator | Capronate | Generator | Hexanoic acid | Generator | Hexoate | Generator | Hexylate | Generator | N-Caproate | Generator | N-Hexanoate | Generator | N-Hexoate | Generator | N-Hexylate | Generator | Pentanecarboxylate | Generator | Pentiformate | Generator | Pentylformate | Generator | Caproate | Generator | Hexanoic acid, calcium salt | MeSH, HMDB | Hexanoic acid, sodium salt, 1-(11)C-labeled | MeSH, HMDB | Hexanoic acid, nickel (2+) salt | MeSH, HMDB | Hexanoic acid, sodium salt | MeSH, HMDB | Bismuth(III)hexanoate | MeSH, HMDB | Hexanoic acid, copper (2+) salt | MeSH, HMDB | Hexanoic acid, manganese (2+) salt | MeSH, HMDB | Bi(ohex)3 | MeSH, HMDB | Hexanoic acid, barium salt | MeSH, HMDB | Hexanoic acid, potassium salt | MeSH, HMDB | Hexanoic acid, rhodium (2+) salt | MeSH, HMDB | FA(6:0) | HMDB | Calcium N-hexanoate | MeSH, HMDB | Hexanoic acid, sodium salt (1:1) | MeSH, HMDB | Sodium capronate | MeSH, HMDB | Calcium hexanoate | MeSH, HMDB | Caproic acid sodium salt | MeSH, HMDB | Sodium caproate | MeSH, HMDB | Sodium hexanoate | MeSH, HMDB | Caproic acid | db_source | FEMA 2559 | db_source | Pentane-1-carboxylic acid | db_source |
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Predicted Properties | |
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Chemical Formula | C6H12O2 |
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IUPAC name | hexanoic acid |
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InChI Identifier | InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) |
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InChI Key | FUZZWVXGSFPDMH-UHFFFAOYSA-N |
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Isomeric SMILES | CCCCCC(O)=O |
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Average Molecular Weight | 116.1583 |
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Monoisotopic Molecular Weight | 116.083729628 |
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Classification |
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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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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 62.04%; H 10.41%; O 27.55% | DFC |
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Melting Point | Fp -1.5° | DFC |
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Boiling Point | Bp 205° | DFC |
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Experimental Water Solubility | 10.3 mg/mL at 25 oC | YALKOWSKY,SH & HE,Y (2003) |
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Experimental logP | 1.92 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa1 4.8 (25°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d154 0.93 | DFC |
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Refractive Index | n20D 1.4164 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-03di-9000000000-fe3fab44832ddab1082e | 2014-09-20 | View Spectrum | GC-MS | Sedanoic acid, 1 TMS, GC-MS Spectrum | splash10-00yi-3900000000-8d7942410dfae70c7c9d | Spectrum | GC-MS | Sedanoic acid, non-derivatized, GC-MS Spectrum | splash10-03di-9000000000-f4bf00b677d90d54ba69 | Spectrum | GC-MS | Sedanoic acid, non-derivatized, GC-MS Spectrum | splash10-00yi-3900000000-8d7942410dfae70c7c9d | Spectrum | Predicted GC-MS | Sedanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9000000000-9ee618fa3c0bd9d56748 | Spectrum | Predicted GC-MS | Sedanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00fr-9200000000-be939d8c0455d1af93a6 | Spectrum | Predicted GC-MS | Sedanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sedanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Sedanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-014i-0900000000-ba8c7078846c268d61a6 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-03di-0900000000-151d5971be58b6799d2e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-02t9-1900000000-36096ef7dfebaa193910 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-03di-9000000000-f4bf00b677d90d54ba69 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-f5b00c5e9d90d801ab16 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-014i-0900000000-5013166dd3b692762812 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-014i-5900000000-52b3e7f8b01498621772 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-e3af905666760ff49069 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-f5b00c5e9d90d801ab16 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-5013166dd3b692762812 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-5900000000-52b3e7f8b01498621772 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-e3af905666760ff49069 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-01b9-6900000000-763e9a8e0f15e13fae3c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0002-9000000000-df670aaa002d77689cc7 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-9700000000-5489131065e0934751a7 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fs-9100000000-68f7c2883fb339578ace | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9000000000-8e5e925d60baa2f176c2 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-e877f22e42e8323f59e3 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01b9-9800000000-b5d583466919719819a1 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-791ecce51d7cdde8f0f5 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05tg-9000000000-b176d73a7b4fabde1ad4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006x-9000000000-08e066ae069da04a8689 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-808b7302aa744c7a1c20 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-21c5ae8d52f2e0f4cd33 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-9000000000-3e67c250e6a67f63a0dd | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 8552 |
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ChEMBL ID | CHEMBL14184 |
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KEGG Compound ID | C01585 |
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Pubchem Compound ID | 8892 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 30776 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00535 |
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CRC / DFC (Dictionary of Food Compounds) ID | JJQ79-J:JJQ79-J |
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EAFUS ID | 1629 |
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Dr. Duke ID | CAPRONIC-ACID|CAPROIC-ACID|HEXOIC-ACID|HEXANOIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001218 |
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HET ID | 6NA |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 142-62-1 |
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GoodScent ID | rw1008541 |
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SuperScent ID | 8892 |
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Wikipedia ID | Hexanoic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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acidulant | 64047 | Any substance which is added to food to preserve or enhance its flavour and/or appearance. | DUKE | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | irritant | | | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Peroxisomal carnitine O-octanoyltransferase | CROT | Q9UKG9 | Carnitine O-palmitoyltransferase 2, mitochondrial | CPT2 | P23786 | Mitochondrial carnitine/acylcarnitine carrier protein | SLC25A20 | O43772 |
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Pathways | Name | SMPDB Link | KEGG Link |
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Beta Oxidation of Very Long Chain Fatty Acids | SMP00052 | map01040 | Fatty Acid Biosynthesis | SMP00456 | Not Available | Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids | SMP00480 | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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sweat |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| cheese |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sour |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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