Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:01 UTC |
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Update date | 2019-11-26 03:02:26 UTC |
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Primary ID | FDB008305 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (E)-Aconitic acid |
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Description | Isolated from Asarum europaeum, from cane-sugar molasses, roasted chicory root, roasted malt barley, passion fruit, sorghum root and sugar beet. Flavouring agent used in fruit flavours and alcoholic beverages. Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerisation of citrate to isocitrate in the citric acid cycle. It is acted upon by aconitase. Trans-aconitate in the urine is a biomarker for the consumption of soy products. (E)-Aconitic acid is found in many foods, some of which are cereals and cereal products, rice, garden tomato (variety), and root vegetables. |
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CAS Number | 4023-65-8 |
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Structure | |
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Synonyms | Synonym | Source |
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(1E)-1-Propene-1,2,3-tricarboxylic acid | ChEBI | (e)-1-Propene-1,2,3-tricarboxylic acid | ChEBI | (1E)-1-Propene-1,2,3-tricarboxylate | Generator | (e)-1-Propene-1,2,3-tricarboxylate | Generator | trans-Aconitate | Generator | (1E)-Prop-1-ene-1,2,3-tricarboxylic | HMDB | (1E)1-Propene-1,2,3-tricarboxylate | HMDB | (1E)1-Propene-1,2,3-tricarboxylic acid | HMDB | (e)-Aconitic acid | HMDB | 1-Propene-1-trans-2,3-tricarboxylic acid | HMDB | 1-trans-Propene-1,2,3-tricarboxylic acid | HMDB | Acid | HMDB | TRA | HMDB | trans-1-Propene-1,2,3-tricarboxylic acid | HMDB | trans-Propene-1,2,3-tricarboxylic acid | HMDB | Acid, aconitic | HMDB | Acid, adonic | HMDB | Acid, carboxyglutaconic | HMDB | Acid, citridic | HMDB | Adonic acid | HMDB | Achilleic acid | HMDB | Acid, acontic | HMDB | Acid, pyrocitric | HMDB | Carboxyglutaconic acid | HMDB | Equisetic acid | HMDB | Pyrocitric acid | HMDB | Acid, achilleic | HMDB | Acid, equisetic | HMDB | Aconitate | HMDB | Citridic acid | HMDB | Citridinic acid | HMDB | Acid, citridinic | HMDB | Aconitic acid | HMDB | Acontic acid | HMDB | (1e)-1-Propene-1,2,3-tricarboxylate | Generator | (1e)-Prop-1-ene-1,2,3-tricarboxylic | HMDB | (1E)-Prop-1-ene-1,2,3-tricarboxylic acid | biospider | (1e)1-Propene-1,2,3-tricarboxylate | HMDB | (1e)1-Propene-1,2,3-tricarboxylic acid | HMDB | (E)-1-Propene-1,2,3-tricarboxylic acid | biospider | (E)-Aconitic acid | biospider | 1-Propene-1,2,3-tricarboxylic acid, (1E)- | biospider | 1-Propene-1,2,3-tricarboxylic acid, (E)- (8CI)(9CI) | biospider | Aconitic acid, trans | biospider | trans-Aconitic acid | biospider |
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Predicted Properties | |
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Chemical Formula | C6H6O6 |
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IUPAC name | (1E)-prop-1-ene-1,2,3-tricarboxylic acid |
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InChI Identifier | InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+ |
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InChI Key | GTZCVFVGUGFEME-HNQUOIGGSA-N |
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Isomeric SMILES | OC(=O)C\C(=C/C(O)=O)C(O)=O |
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Average Molecular Weight | 174.1082 |
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Monoisotopic Molecular Weight | 174.016437924 |
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Classification |
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Description | Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Tricarboxylic acids and derivatives |
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Direct Parent | Tricarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Tricarboxylic acid or derivatives
- Carboxylic acid
- 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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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 41.39%; H 3.47%; O 55.14% | DFC |
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Melting Point | Mp 194-195° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | pKa2 4.46 (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 | Not Available | |
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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) | splash10-000f-9100000000-814aded0eac117ddb550 | 2015-03-01 | View Spectrum | GC-MS | (E)-Aconitic acid, 3 TMS, GC-MS Spectrum | splash10-003s-3971000000-d4adfdbddf5dc3badb47 | Spectrum | GC-MS | (E)-Aconitic acid, non-derivatized, GC-MS Spectrum | splash10-003s-3971000000-d4adfdbddf5dc3badb47 | Spectrum | GC-MS | (E)-Aconitic acid, non-derivatized, GC-MS Spectrum | splash10-0002-1930000000-1043e640a069e4ed3c64 | Spectrum | Predicted GC-MS | (E)-Aconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-06w9-4900000000-38239492ad0e66d6533b | Spectrum | Predicted GC-MS | (E)-Aconitic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9167000000-07ccdac5775cc3e75c95 | Spectrum | Predicted GC-MS | (E)-Aconitic acid, non-derivatized, 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, Positive (Annotated) | splash10-000i-9300000000-1f04239a9a7133f89d08 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000f-9000000000-49f5c2a7959cfbbbe09f | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000f-9100000000-d4857c30b96cf4786dbe | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00b9-1900000000-51343d1269f884535cca | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9100000000-b3ebe9a6fedcb9608872 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-2d6b96d6e5ed92f0fdee | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-000l-9000000000-d36114a1c7a0318b1f7a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-f4ae4a72d5f2beed9106 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-000i-9200000000-49eaf4d6558839930e52 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00b9-1900000000-51343d1269f884535cca | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9100000000-b3ebe9a6fedcb9608872 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-4f60fbd245c1d58cd7d5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000l-9000000000-d36114a1c7a0318b1f7a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-f4ae4a72d5f2beed9106 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-9200000000-49eaf4d6558839930e52 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9100000000-a70cb799a63ff364ca21 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000f-9000000000-eabb8ab38f98bb81b1ee | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000i-9200000000-2d22108854c0dad1b598 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000i-9300000000-3cf209c9f766f6c0efe8 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-8e26562af9ae45eb3303 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02di-1900000000-7fec32a5e34c3b55d683 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01w0-9600000000-ee172c3013370ab0da31 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00fr-1900000000-18635ce5a20ce1b78139 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00b9-2900000000-58bb75a2a1b28dbffd73 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06rf-9300000000-19df730d01f07fcf6573 | 2016-09-12 | 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, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C 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 | 392201 |
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ChEMBL ID | CHEMBL153658 |
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KEGG Compound ID | C02341 |
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Pubchem Compound ID | 444212 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 32806 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00958 |
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CRC / DFC (Dictionary of Food Compounds) ID | DFV04-S:DFV05-T |
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EAFUS ID | Not Available |
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Dr. Duke ID | TRANS-ACONITIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1001681 |
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SuperScent ID | Not Available |
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Wikipedia ID | Aconitic_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 feedant | | | 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 | Not Available |
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Pathways | 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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vegetable |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| musty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| nut |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| dry |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| toasted |
- 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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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