Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 21:47:07 UTC |
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Update Date | 2022-03-07 02:55:00 UTC |
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HMDB ID | HMDB0036623 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Deoxycohumulone |
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Description | 4-Deoxycohumulone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-Deoxycohumulone has been detected, but not quantified in, alcoholic beverages. This could make 4-deoxycohumulone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Deoxycohumulone. |
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Structure | CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O InChI=1S/C20H28O4/c1-11(2)7-9-14-18(22)15(10-8-12(3)4)20(24)16(19(14)23)17(21)13(5)6/h7-8,13,22-24H,9-10H2,1-6H3 |
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Synonyms | Value | Source |
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3,5-Bis(3-methyl-2-butenyl)phlorisobutyrophenone | ChEBI | 3,5-Diprenylphlorisobutyrophenone | ChEBI | Diprenylphlorisobutyrophenone | ChEBI | 2',4',6'-Trihydroxy-2-methyl-3',5'-bis(3-methyl-2-butenyl)propiophenone, 8ci | HMDB | 2,4-Bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-1,3,5-cyclohexanetrione, 9ci | HMDB | Deoxycohumulone | MeSH |
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Chemical Formula | C20H28O4 |
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Average Molecular Weight | 332.4339 |
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Monoisotopic Molecular Weight | 332.198759384 |
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IUPAC Name | 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]propan-1-one |
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Traditional Name | 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]propan-1-one |
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CAS Registry Number | 5880-42-2 |
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SMILES | CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O |
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InChI Identifier | InChI=1S/C20H28O4/c1-11(2)7-9-14-18(22)15(10-8-12(3)4)20(24)16(19(14)23)17(21)13(5)6/h7-8,13,22-24H,9-10H2,1-6H3 |
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InChI Key | KKFIZYKKQLWBKH-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. |
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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 | Alkyl-phenylketones |
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Alternative Parents | |
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Substituents | - Alkyl-phenylketone
- Acylphloroglucinol derivative
- Phloroglucinol derivative
- Phenylpropane
- Benzenetriol
- Aryl alkyl ketone
- Benzoyl
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Polyol
- Organic oxide
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-Deoxycohumulone,1TMS,isomer #1 | CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O | 2463.4 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,1TMS,isomer #2 | CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C | 2461.0 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,2TMS,isomer #1 | CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C | 2489.9 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,2TMS,isomer #2 | CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C | 2474.0 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,3TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C | 2568.6 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,1TBDMS,isomer #1 | CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O | 2677.5 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,1TBDMS,isomer #2 | CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C | 2679.1 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,2TBDMS,isomer #1 | CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C | 2943.4 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,2TBDMS,isomer #2 | CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C | 2940.3 | Semi standard non polar | 33892256 | 4-Deoxycohumulone,3TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C | 3190.0 | Semi standard non polar | 33892256 |
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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 - 4-Deoxycohumulone GC-MS (Non-derivatized) - 70eV, Positive | splash10-000f-4193000000-41b8d6cdc2cbf9ee766f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Deoxycohumulone GC-MS (3 TMS) - 70eV, Positive | splash10-053r-2101290000-879af4d98c4d42b0352b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Deoxycohumulone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Deoxycohumulone 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Positive-QTOF | splash10-001i-1049000000-fa9e67c269612fcf3a89 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Positive-QTOF | splash10-01c0-8095000000-bd6c7081797f5e97a560 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Positive-QTOF | splash10-06dl-9140000000-5e23e20c4035a4e3aae3 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Negative-QTOF | splash10-001i-0019000000-5b760f22b28210196ced | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Negative-QTOF | splash10-03di-3093000000-3a4ad204f16782971540 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Negative-QTOF | splash10-00di-9771000000-83e53b35e9c6c2f16f11 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Positive-QTOF | splash10-001i-0039000000-ea2f4fd713f4676e050a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Positive-QTOF | splash10-00li-0090000000-cf43683013a9a540b3b7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Positive-QTOF | splash10-0fyo-1090000000-5fea635e9161c6141e04 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Negative-QTOF | splash10-001i-0009000000-bd69facddc36af19b908 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Negative-QTOF | splash10-001i-0039000000-3840b37c3d39866bcf88 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Negative-QTOF | splash10-0a4m-3390000000-18b240fc25783028d6e0 | 2021-09-22 | Wishart Lab | View Spectrum |
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