Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:40:15 UTC |
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Updated at | 2021-08-19 23:59:22 UTC |
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NP-MRD ID | NP0002780 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 2-Hexenal |
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Provided By | BMRB |
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Description | 2-Hexenal, also known as (e)-hex-2-enal or b-propyl acrolein, 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. Thus, 2-hexenal is considered to be a fatty aldehyde. 2-Hexenal is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2-Hexenal is found in Aethus indicus, Ageratum conyzoides, Aloe arborescens, Aristolochia debilis, Basella alba, Thea sinensis , Capillipedium parviflorum, Capparis spinosa, Citrus limon, Citrus sinensis, Clinopodium serpyllifolium, Dianthus caryophyllus L. , Echinophora tenuifolia, Euploea sylvester, Farfugium japonicum, Gonioctena viminalis, Lonicera japonica, Micromeria maderensis, Nelumbo nucifera, Nepeta racemosa, Origanum sipyleum, Origanum vulgare, Peristeria elata, Petasites albus , Pimenta racemosa, Quercus agrifolia, Riptortus clavatus, Robinia pseudoacacia, Salvia sclarea, Brassica hirta and Thymus longicaulis. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on 2-Hexenal (PMID: 22626821) (PMID: 21548650) (PMID: 22177713) (PMID: 22417509). |
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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 Mass | 98.1450 Da |
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Monoisotopic Mass | 98.07316 Da |
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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 | Not Available |
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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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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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 | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- 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 ]
- Sakamaki K, Ishizaki S, Ohkubo Y, Tateno Y, Fujita A: Identification of the medicinal off-flavor compound formed from ascorbic acid and (E)-hex-2-enal. J Agric Food Chem. 2011 Jun 22;59(12):6667-71. doi: 10.1021/jf200846h. Epub 2011 May 23. [PubMed:21548650 ]
- Joo MJ, Merkel C, Auras R, Almenar E: Development and characterization of antimicrobial poly(l-lactic acid) containing trans-2-hexenal trapped in cyclodextrins. Int J Food Microbiol. 2012 Feb 15;153(3):297-305. doi: 10.1016/j.ijfoodmicro.2011.11.015. Epub 2011 Nov 29. [PubMed:22177713 ]
- De Lucca AJ, Carter-Wientjes CH, Boue S, Bhatnagar D: Volatile trans-2-hexenal, a soybean aldehyde, inhibits Aspergillus flavus growth and aflatoxin production in corn. J Food Sci. 2011 Aug;76(6):M381-6. doi: 10.1111/j.1750-3841.2011.02250.x. [PubMed:22417509 ]
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