| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-08-29 05:51:23 UTC |
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| Update Date | 2014-12-24 20:26:41 UTC |
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| Accession Number | T3D4189 |
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| Identification |
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| Common Name | 2-Hexenal |
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| Class | Small Molecule |
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| Description | 2-Hexenal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
2-Hexenal is found in allspice. 2-Hexenal is used in perfumery and flavourings. 2-Hexenal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms. |
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| Compound Type | - Aldehyde
- Ester
- Flavouring Agent
- Food Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Uremic Toxin
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| Chemical Structure | |
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| Synonyms | | Synonym | | 2-Hexen-1-al | | 3-Propyl acrolein | | 3-Propylacrolein | | beta-Propyl acrolein | | beta-Propylacrolein | | FEMA 2560 | | Hex-2-en-1-al | | Hex-2-enal | | Hexenal | | Hexylenic aldehyde |
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| Chemical Formula | C6H10O |
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| Average Molecular Mass | 98.143 g/mol |
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| Monoisotopic Mass | 98.073 g/mol |
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| CAS Registry Number | 505-57-7 |
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| IUPAC Name | hex-2-enal |
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| Traditional Name | hexenal |
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| SMILES | [H]\C(CCC)=C(\[H])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 | InChIKey=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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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05r0-9000000000-f80d6978daedea323aa6 | 2017-09-01 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-db77fc4d5edd7bdc3907 | 2015-05-27 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000t-9000000000-8c4cc267531a0c711b32 | 2015-05-27 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9000000000-1018f15c3b2d6e22c226 | 2015-05-27 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-9232ec723afab464ccc2 | 2015-05-27 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-a839e50ee7ad7503877e | 2015-05-27 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-4a1d88a16ebce778de70 | 2015-05-27 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0540-9000000000-6923af674dd120606957 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-9000000000-3ea4a5ca74032209afaf | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0573-9000000000-b0552bcc819f05df9c04 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-649f52184fb4997b20fb | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-3e77d5cdc17bcd3c255e | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0n2d-9000000000-022c1508f6a2751bcc39 | 2021-10-12 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Endogenous, Ingestion, Dermal (contact) |
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| Mechanism of Toxicity | Uremic toxins such as 2-Hexenal are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (2). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (3). |
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| Metabolism | Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Naturally produced by the body (endogenous). |
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| Minimum Risk Level | Not Available |
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| Health Effects | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
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| Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
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| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB31496 |
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| PubChem Compound ID | 5281168 |
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| ChEMBL ID | Not Available |
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| ChemSpider ID | 4444608 |
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| KEGG ID | C08497 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | Not Available |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | T3D4189.pdf |
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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. [22626821 ]
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. [22419041 ]
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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