Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2012-09-11 17:43:40 UTC |
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Update Date | 2022-03-07 02:53:00 UTC |
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HMDB ID | HMDB0031496 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Hexenal |
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Description | 2-Hexenal (CAS: 505-57-7), also known as 2-hexenaldehyde or 3-propylacrolein, belongs to the class of organic compounds known as medium-chain aldehydes. These are aldehydes with a chain length containing between 6 and 12 carbon atoms. Thus, 2-hexenal is considered to be a fatty aldehyde lipid molecule. Outside of the human body, 2-hexenal is found, on average, in the highest concentration within a few different foods, such as corn, tea, and bilberries. 2-Hexenal has also been detected, but not quantified in, several different foods, such as common wheat, ginkgo nuts, spearmints, sunflowers, and watermelons. This could make 2-hexenal a potential biomarker for the consumption of these foods. (E)-2-Hexenal is found in allspice. It is used in perfumery and flavouring. (E)-2-Hexenal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). |
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Structure | InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+ |
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Synonyms | Value | Source |
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(e)-2-Hexenal | ChEBI | (e)-Hex--2-enal | ChEBI | (e)-Hex-2-enal | ChEBI | 2-trans-Hexenal | ChEBI | 3-Propylacrolein | ChEBI | beta-Propyl acrolein | ChEBI | beta-Propylacrolein | ChEBI | Leaf aldehyde | ChEBI | trans-2-Hexenal | ChEBI | b-Propyl acrolein | Generator | Β-propyl acrolein | Generator | b-Propylacrolein | Generator | Β-propylacrolein | Generator | Hex-2-en-1-al | HMDB | 2-Hexenal, e | HMDB | (2E)-2-Hexenal | HMDB | (2E)-Hexenal | HMDB | (e)-2-Hexen-1-al | HMDB | 2-Hexen-1-al | HMDB | Hex-2-enal | HMDB | trans-2-Hexen-1-al | HMDB | 2-Hexenaldehyde | HMDB | 3-Propyl-acrolein | HMDB | Hexen-2-al | HMDB | Hexen-2-en-1-al | HMDB | Hexylenic aldehyde | HMDB | alpha,beta-Hexylenaldehyde | HMDB | Α,β-hexylenaldehyde | HMDB | Green leaf aldehyde | HMDB | 2-Hexenal | MeSH |
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Chemical Formula | C6H10O |
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Average Molecular Weight | 98.145 |
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Monoisotopic Molecular Weight | 98.073164942 |
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IUPAC Name | (2E)-hex-2-enal |
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Traditional Name | (E)-2-hexenal |
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CAS Registry Number | 6728-26-3 |
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SMILES | CCC\C=C\C=O |
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InChI Identifier | InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+ |
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InChI Key | MBDOYVRWFFCFHM-SNAWJCMRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Medium-chain aldehydes |
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Alternative Parents | |
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Substituents | - Medium-chain aldehyde
- Enal
- Alpha,beta-unsaturated aldehyde
- Organic oxide
- Hydrocarbon derivative
- 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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Not Available | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | |
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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 IndicesUnderivatized |
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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 - 2-Hexenal GC-MS (Non-derivatized) - 70eV, Positive | splash10-00or-9000000000-ef8fb4a16f9e47588e24 | 2018-04-09 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hexenal GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hexenal LC-ESI-QTOF 32V, positive-QTOF | splash10-0002-9000000000-ea4667e9ee10cccddb24 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hexenal LC-ESI-QFT , positive-QTOF | splash10-0a4j-9000000000-13fcd86dcfc328ec27a6 | 2020-07-21 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 10V, Negative-QTOF | splash10-0002-9000000000-9232ec723afab464ccc2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 20V, Negative-QTOF | splash10-0002-9000000000-a839e50ee7ad7503877e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 40V, Negative-QTOF | splash10-0006-9000000000-4a1d88a16ebce778de70 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 10V, Negative-QTOF | splash10-0002-9000000000-649f52184fb4997b20fb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 20V, Negative-QTOF | splash10-004i-9000000000-3e77d5cdc17bcd3c255e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 40V, Negative-QTOF | splash10-0n2d-9000000000-022c1508f6a2751bcc39 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 10V, Positive-QTOF | splash10-0002-9000000000-db77fc4d5edd7bdc3907 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 20V, Positive-QTOF | splash10-000t-9000000000-8c4cc267531a0c711b32 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 40V, Positive-QTOF | splash10-0a4l-9000000000-1018f15c3b2d6e22c226 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 10V, Positive-QTOF | splash10-0540-9000000000-6923af674dd120606957 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 20V, Positive-QTOF | splash10-052r-9000000000-3ea4a5ca74032209afaf | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hexenal 40V, Positive-QTOF | splash10-0573-9000000000-b0552bcc819f05df9c04 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | 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 | 0.23 +/- 0.07 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.63 +/- 0.21 uM | Adult (>18 years old) | Both | uremia | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Clostridium difficile infection | | details |
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Associated Disorders and Diseases |
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Disease References | Uremia |
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- Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
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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 | FDB004502 |
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KNApSAcK ID | C00000351 |
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Chemspider ID | 4444608 |
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KEGG Compound ID | C08497 |
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BioCyc ID | TRANS-2-HEXENAL |
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BiGG ID | Not Available |
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Wikipedia Link | Cis-3-Hexenal |
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METLIN ID | Not Available |
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PubChem Compound | 5281168 |
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PDB ID | Not Available |
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ChEBI ID | 28913 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00029832 |
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Good Scents ID | rw1013831 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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