Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:11 UTC |
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Update date | 2020-09-17 15:35:41 UTC |
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Primary ID | FDB010553 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3,4-Methylenedioxybenzaldehyde |
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Description | Piperonal or 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. Piperonal is an organic compound which is commonly found in fragrances and flavors. Piperonal occurs naturally in various plants including dill, vanilla, violet flowers, and black pepper. Piperonal has been detected, but not quantified, in several different foods, such as highbush blueberries, pepper (spice), rabbiteye blueberries, and vanilla. Piperonal has a floral odor which is commonly described as being similar to that of vanillin or cherry. For this reason, it is commonly used in fragrances and artificial flavors (https://doi.org/10.1002/14356007.a11_141). |
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CAS Number | 120-57-0 |
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Structure | |
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Synonyms | Synonym | 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 | 1,3-Benzodioxole-5-carboxaldehyde, 9CI | db_source | 3,4-METHYLEN-DIOXY-BENZALDEHYDE | biospider | Benzaldehyde, 3,4-(methylenedioxy)- | biospider | Blue p | biospider | Piperonal, 8CI | db_source |
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Predicted Properties | |
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Chemical Formula | C8H6O3 |
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IUPAC name | 2H-1,3-benzodioxole-5-carbaldehyde |
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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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Isomeric SMILES | [H]C(=O)C1=CC2=C(OCO2)C=C1 |
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Average Molecular Weight | 150.1314 |
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Monoisotopic Molecular Weight | 150.031694058 |
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Classification |
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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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 64.00%; H 4.03%; O 31.97% | DFC |
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Melting Point | Mp 37° | DFC |
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Boiling Point | Bp15 140° | DFC |
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Experimental Water Solubility | 3.5 mg/mL at 20 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 1.05 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0f6t-5900000000-deaf6988b3684d4c20e3 | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0udj-0900000000-b5bce0817d3b7da073b5 | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0udj-2900000000-dd3223a5400ccb92654c | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0f6t-5900000000-f62030c087954cb17793 | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0gvk-5900000000-8a0279ec82445d96e75a | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0f6t-5900000000-deaf6988b3684d4c20e3 | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0udj-0900000000-b5bce0817d3b7da073b5 | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0udj-2900000000-dd3223a5400ccb92654c | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0f6t-5900000000-f62030c087954cb17793 | Spectrum | GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-0gvk-5900000000-8a0279ec82445d96e75a | Spectrum | Predicted GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fk9-5900000000-18459b3a00c1178d35a1 | Spectrum | Predicted GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3,4-Methylenedioxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udi-0900000000-b5b6834400d9d6682544 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udi-0900000000-84dd85011e2ee53f2419 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-0udi-1900000000-62ac1d8f95baaaa86cdc | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-0udi-2900000000-845d915e801880fe515e | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-0ukc-4900000000-a2da771088f9bd903b28 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-0fdo-7900000000-6d6138acd0b07ffaf80f | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-0006-9600000000-50b7e072efe444eab046 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, positive | splash10-0006-9400000000-a00479fe5850665b281a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, positive | splash10-00kf-9100000000-d767f739422c110699e1 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-014i-9000000000-2c58ea01cf6deb1fd0cb | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, positive | splash10-014i-9000000000-e1b8a3928f36d4c767f0 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, positive | splash10-014i-9000000000-9a1a6e1587039d548c14 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, positive | splash10-014i-9000000000-8cba8d9c4f8d5695ce7f | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-00di-1900000000-54afeb3dfd71c9fcd607 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-014i-9000000000-02653bad35d931248654 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-004i-9000000000-791c4364189bf936d4c3 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-0006-9000000000-e67da0571423f0e6b4b8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-00di-1900000000-94cc28f3d5f593c40e43 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-00di-1900000000-64a29a0890bb37965f42 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900000000-e5e34bc7a3df137e69de | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-7dea1b5613bf810c5aa5 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0l90-7900000000-0505f5c9e1fbdc94057b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-b0c81ffa7cb223383909 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-7ff4ed41bbe2ad283eda | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-9700000000-abb6ae8bee74f8c6ae31 | 2016-09-12 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 13859497 |
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ChEMBL ID | CHEMBL271663 |
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KEGG Compound ID | C10812 |
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Pubchem Compound ID | 8438 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 8240 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB32612 |
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CRC / DFC (Dictionary of Food Compounds) ID | FCW86-Y:FCW86-Y |
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EAFUS ID | 3060 |
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Dr. Duke ID | PIPERONAL|HELIOTROPIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002666 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1005891 |
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SuperScent ID | 8438 |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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violet |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| heliotrope |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| flower |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| powdery |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| coconut |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| vanilla |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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