Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:58 UTC |
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Update date | 2020-04-21 18:03:35 UTC |
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Primary ID | FDB012062 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Butanoic acid |
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Description | Found in fresh and cooked apples, banana, sour cherry, papaya, strawberries, wheat bread, cheeses, butter and coffee. Flavouring agent
Butyric acid (from Greek ???????? = butter), also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH. Salts and esters of butyric acid are known as butyrates or butanoates. Butyric acid is found in rancid butter, parmesan cheese, vomit, and body odor and has an unpleasant smell and acrid taste, with a sweetish aftertaste (similar to ether). It can be detected by mammals with good scent detection abilities (such as dogs) at 10 ppb, whereas humans can detect it in concentrations above 10 ppm.; Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. The triglyceride of butyric acid makes up 3% to 4% of butter. When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis leading to the unpleasant odor. It is an important member of the fatty acid sub-group called short chain fatty acids. Butyric acid is a weak acid with a pKa of 4.82, similar to acetic acid which has pKa 4.76. The similar strength of these acids results from their common -CH2COOH terminal structure. Pure butyric acid is 10.9 molar.; Butyric acid, a four-carbon fatty acid, is formed in the human colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC). Butyrate has diverse and apparently paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate and the intracellular milieu. In humans, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis. Perhaps not surprisingly, results of these investigations have been mutually contradictory. The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results. In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon. (PMID: 16460475) Butyric acid is a carboxylic acid found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.; The acid is an oily colorless liquid that is easily soluble in water, ethanol, and ether, and can be separated from an aqueous phase by saturation with salts such as calcium chloride. Potassium dichromate and sulfuric acid oxidize it to carbon dioxide and acetic acid, while alkaline potassium permanganate oxidizes it to carbon dioxide. The calcium salt, Ca(C4H7O2)2·H2O, is less soluble in hot water than in cold. |
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CAS Number | 107-92-6 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Butanoic acid | ChEBI | 1-Butyric acid | ChEBI | 1-Propanecarboxylic acid | ChEBI | 4:0 | ChEBI | Acide butanoique | ChEBI | Acide butyrique | ChEBI | Butanic acid | ChEBI | Butanoate | ChEBI | Butanoic acid | ChEBI | Butoic acid | ChEBI | Buttersaeure | ChEBI | C4:0 | ChEBI | CH3-[CH2]2-COOH | ChEBI | Ethylacetic acid | ChEBI | N-Butanoic acid | ChEBI | N-Butyric acid | ChEBI | Propanecarboxylic acid | ChEBI | Propylformic acid | ChEBI | Butyrate | Kegg | 1-Butanoate | Generator | 1-Butyrate | Generator | 1-Propanecarboxylate | Generator | Butanate | Generator | Butoate | Generator | Ethylacetate | Generator | N-Butanoate | Generator | N-Butyrate | Generator | Propanecarboxylate | Generator | Propylformate | Generator | Honey robber | HMDB | Kyselina maselna | HMDB | Butyrate, magnesium | HMDB | Magnesium butyrate | HMDB | Acid, butyric | HMDB | Butyrate, sodium | HMDB | Dibutyrate, magnesium | HMDB | Magnesium dibutyrate | HMDB | Sodium butyrate | HMDB | Acid, butanoic | HMDB | Butyric acid magnesium salt | HMDB | Butyric acid, sodium salt | HMDB | FA(4:0) | HMDB | Butyric acid | KEGG | 1-butanoate | biospider | 1-butanoic acid | biospider | 1ugp | biospider | 2-butanoate | biospider | BEO | biospider | BUA | biospider | butanoic acid, 4 | biospider | Butyrate (n-C4:0) | biospider | Butyrate, sodium salt | biospider | Butyric acid [UN2820] [Corrosive] | biospider | Butyric_acid | biospider | Ethyacetic acid | biospider | FEMA 2221 | db_source | N-butanoate | biospider | N-butanoic acid | biospider | N-butyrate | biospider | N-butyric acid | biospider | n-C3H7COOH | biospider |
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Predicted Properties | |
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Chemical Formula | C4H8O2 |
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IUPAC name | butanoic acid |
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InChI Identifier | InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) |
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InChI Key | FERIUCNNQQJTOY-UHFFFAOYSA-N |
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Isomeric SMILES | CCCC(O)=O |
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Average Molecular Weight | 88.1051 |
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Monoisotopic Molecular Weight | 88.0524295 |
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Classification |
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Description | Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. |
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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 | Straight chain fatty acids |
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Alternative Parents | |
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Substituents | - 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 | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 54.53%; H 9.15%; O 36.32% | DFC |
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Melting Point | Mp -8° | DFC |
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Boiling Point | Bp 163.5° | DFC |
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Experimental Water Solubility | 60 mg/mL at 25 oC | HEMPHILL,L & SWANSON,WS (1964) |
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Experimental logP | 0.79 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 4.82 (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 | d204 0.96 | DFC |
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Refractive Index | Not Available | |
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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-9000000000-5338ff8a9c4e59150aba | 2014-09-20 | View Spectrum | GC-MS | Butanoic acid, non-derivatized, GC-MS Spectrum | splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1 | Spectrum | GC-MS | Butanoic acid, non-derivatized, GC-MS Spectrum | splash10-03dl-9000000000-032fc35b394786b5896a | Spectrum | GC-MS | Butanoic acid, non-derivatized, GC-MS Spectrum | splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1 | Spectrum | GC-MS | Butanoic acid, non-derivatized, GC-MS Spectrum | splash10-03dl-9000000000-032fc35b394786b5896a | Spectrum | Predicted GC-MS | Butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002f-9000000000-a7792b54320e7c859731 | Spectrum | Predicted GC-MS | Butanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00fr-9100000000-d125b331c4a6d37648a1 | Spectrum | Predicted GC-MS | Butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Butanoic 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) | splash10-000i-9000000000-7f461db56bfd8568ec71 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-000i-9000000000-66f857fa612f773837bc | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-000i-9000000000-e6689b2e6bf21570b934 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-03dl-9000000000-b2ffa7d67b2466dea94f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-03dl-9000000000-7467bf19c64fd3f51105 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-9000000000-9ae015043b014b3c93d9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9000000000-e30b3c6bd6218b9b49e1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-efbb0e35a19a1713240b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-9ae015043b014b3c93d9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-e30b3c6bd6218b9b49e1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-efbb0e35a19a1713240b | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-9000000000-acb5cf0017a9ee680dd8 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-9000000000-812e24462a71dccb0fec | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-f9d30338ca1ee9409964 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-9d749b6b6cf2f93a8f85 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00ku-9000000000-ee742730266fb4997777 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-88fc445cddcb726e93d8 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-4b3590a18d40d4d58a01 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014r-9000000000-140190568a3f2b3c6f01 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9000000000-1f7dab1fbd0179ef6d17 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-9000000000-020fcfb652dc5a6f3036 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-3e4b1bc1291a3fbf86c9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-1f57e9adb6de1499caf5 | 2021-09-22 | 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 | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | 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 | 259 |
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ChEMBL ID | CHEMBL14227 |
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KEGG Compound ID | C00246 |
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Pubchem Compound ID | 264 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 30772 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03568 |
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HMDB ID | HMDB00039 |
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CRC / DFC (Dictionary of Food Compounds) ID | HCX15-D:HCX15-D |
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EAFUS ID | 438 |
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Dr. Duke ID | 1-BUTYRIC-ACID|BUTYRIC-ACID|BUTANOIC-ACID|N-BUTYRIC-ACID |
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BIGG ID | 34376 |
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KNApSAcK ID | C00001180 |
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HET ID | BUA |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 107-92-6 |
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GoodScent ID | rw1003411 |
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SuperScent ID | 264 |
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Wikipedia ID | Butyric 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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anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | apoptotic | | | DUKE | bruchifuge | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | nematistat | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Cholinesterase | BCHE | P06276 | Peroxisome proliferator-activated receptor gamma | PPARG | P37231 | Tumor necrosis factor | TNF | P01375 | Histone deacetylase 4 | HDAC4 | P56524 | Histone deacetylase 9 | HDAC9 | Q9UKV0 |
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Pathways | |
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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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rancid |
- 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
| cheese |
- 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
- 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.
| 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
| sharp |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| acetic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| butter |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fruit |
- 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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