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 17:50:47 UTC |
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Update Date | 2023-02-21 17:22:29 UTC |
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HMDB ID | HMDB0032612 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3,4-Methylenedioxybenzaldehyde |
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Description | 3,4-Methylenedioxybenzaldehyde, also known as heliotropin or piperonyl aldehyde, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. 3,4-Methylenedioxybenzaldehyde is a sweet, bitter, and coconut tasting compound. 3,4-Methylenedioxybenzaldehyde has been detected, but not quantified in, several different foods, such as highbush blueberries (Vaccinium corymbosum), pepper (spice), rabbiteye blueberries (Vaccinium virgatum), and vanillas (Vanilla). This could make 3,4-methylenedioxybenzaldehyde a potential biomarker for the consumption of these foods. 3,4-Methylenedioxybenzaldehyde 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. Based on a literature review a significant number of articles have been published on 3,4-Methylenedioxybenzaldehyde. |
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Structure | [H]C(=O)C1=CC2=C(OCO2)C=C1 InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2 |
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Synonyms | Value | Source |
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1,3-Benzodioxole-5-carboxaldehyde | ChEBI | 3,4-(Methylenedioxy)benzaldehyde | ChEBI | 3,4-Dihydroxybenzaldehyde methylene ketal | ChEBI | 5-Formyl-1,3-benzodioxole | ChEBI | Heliotropin | ChEBI | Heliotropine | ChEBI | Piperonaldehyde | ChEBI | Piperonyl aldehyde | ChEBI | Piperonylaldehyde | ChEBI | Protocatechuic aldehyde methylene ether | ChEBI | 1,3-Benzodioxole-5-carbaldehyde | HMDB | 1,3-Benzodioxole-5-carboxaldehyde, 9ci | HMDB | 3, 4-(Methylenedioxy)benzaldehyde | HMDB | 3, 4-Bis(methylenedioxy)benzaldehyde | HMDB | 3,4-(Methylenedioxy)-benzaldehyde | HMDB | 3,4-Bis(methylenedioxy)benzaldehyde | HMDB | 3,4-Dimethylenedioxybenzaldehyde | HMDB | 3,4-METHYLEN-dioxy-benzaldehyde | HMDB | 3,4-Methylene-dihydroxybenzaldehyde | HMDB | Blue P | HMDB | Dioxymethylene protocatechuic aldehyde | HMDB | Dioxymethylene-protocatechuic aldehyde | HMDB | FEMA 2911 | HMDB | Geliotropin | HMDB | Heliotropine (piperonal) | HMDB | Piperanal | HMDB | Piperonal | HMDB | Piperonal, 8ci | HMDB | 3,4-Methylenedioxybenzaldehyde | ChEBI | Heliotrin | MeSH |
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Chemical Formula | C8H6O3 |
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Average Molecular Weight | 150.1314 |
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Monoisotopic Molecular Weight | 150.031694058 |
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IUPAC Name | 2H-1,3-benzodioxole-5-carbaldehyde |
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Traditional Name | piperonal |
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CAS Registry Number | 120-57-0 |
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SMILES | [H]C(=O)C1=CC2=C(OCO2)C=C1 |
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InChI Identifier | InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2 |
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InChI Key | SATCULPHIDQDRE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzodioxoles |
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Sub Class | Not Available |
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Direct Parent | Benzodioxoles |
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Alternative Parents | |
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Substituents | - Benzodioxole
- Aryl-aldehyde
- Benzenoid
- Oxacycle
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aldehyde
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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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 | Property | Value | Reference |
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Melting Point | 37 °C | Not Available | Boiling Point | 263.00 to 265.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 3.5 mg/mL at 20 °C | Not Available | LogP | 1.05 | Not Available |
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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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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0f6t-5900000000-deaf6988b3684d4c20e3 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde CI-B (Non-derivatized) | splash10-0udj-0900000000-b5bce0817d3b7da073b5 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0udj-2900000000-dd3223a5400ccb92654c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0f6t-5900000000-f62030c087954cb17793 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0gvk-5900000000-8a0279ec82445d96e75a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0f6t-5900000000-deaf6988b3684d4c20e3 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde CI-B (Non-derivatized) | splash10-0udj-0900000000-b5bce0817d3b7da073b5 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0udj-2900000000-dd3223a5400ccb92654c | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0f6t-5900000000-f62030c087954cb17793 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized) | splash10-0gvk-5900000000-8a0279ec82445d96e75a | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fk9-5900000000-18459b3a00c1178d35a1 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde 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 - 3,4-Methylenedioxybenzaldehyde Orbitrap 1V, positive-QTOF | splash10-0udi-0900000000-b5b6834400d9d6682544 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 1V, positive-QTOF | splash10-0udi-0900000000-84dd85011e2ee53f2419 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 2V, positive-QTOF | splash10-0udi-1900000000-62ac1d8f95baaaa86cdc | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 2V, positive-QTOF | splash10-0udi-2900000000-845d915e801880fe515e | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 3V, positive-QTOF | splash10-0ukc-4900000000-a2da771088f9bd903b28 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 3V, positive-QTOF | splash10-0fdo-7900000000-6d6138acd0b07ffaf80f | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 3V, positive-QTOF | splash10-0006-9600000000-50b7e072efe444eab046 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 4V, positive-QTOF | splash10-0006-9400000000-a00479fe5850665b281a | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 5V, positive-QTOF | splash10-00kf-9100000000-d767f739422c110699e1 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 6V, positive-QTOF | splash10-014i-9000000000-2c58ea01cf6deb1fd0cb | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 8V, positive-QTOF | splash10-014i-9000000000-e1b8a3928f36d4c767f0 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 9V, positive-QTOF | splash10-014i-9000000000-9a1a6e1587039d548c14 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 11V, positive-QTOF | splash10-014i-9000000000-8cba8d9c4f8d5695ce7f | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOF | splash10-00di-1900000000-54afeb3dfd71c9fcd607 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOF | splash10-014i-9000000000-02653bad35d931248654 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOF | splash10-004i-9000000000-791c4364189bf936d4c3 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOF | splash10-0006-9000000000-e67da0571423f0e6b4b8 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 0V, positive-QTOF | splash10-00di-1900000000-94cc28f3d5f593c40e43 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 1V, positive-QTOF | splash10-00di-1900000000-64a29a0890bb37965f42 | 2020-07-22 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 10V, Positive-QTOF | splash10-0udi-0900000000-e5e34bc7a3df137e69de | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 20V, Positive-QTOF | splash10-0udi-0900000000-7dea1b5613bf810c5aa5 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 40V, Positive-QTOF | splash10-0l90-7900000000-0505f5c9e1fbdc94057b | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 10V, Negative-QTOF | splash10-0002-0900000000-b0c81ffa7cb223383909 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 20V, Negative-QTOF | splash10-0002-0900000000-7ff4ed41bbe2ad283eda | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 40V, Negative-QTOF | splash10-0002-9700000000-abb6ae8bee74f8c6ae31 | 2016-09-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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