Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:58 UTC |
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Update date | 2019-11-26 03:06:06 UTC |
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Primary ID | FDB012060 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3,4-Dihydroxybenzaldehyde |
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Description | Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus . |
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CAS Number | 139-85-5 |
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Structure | |
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Synonyms | Synonym | Source |
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1,2-Dihydroxy-4-formylbenzene | ChEBI | 3,4-Dihydroxybenzenecarbonal | ChEBI | 4-Formyl-1,2-benzenediol | ChEBI | 4-Formyl-1,2-dihydroxybenzene | ChEBI | Protocatechualdehyde | ChEBI | Protocatechuic aldehyde | ChEBI | Protocatechualdehyde, 3H-labeled | MeSH | Rancinamycin IV | MeSH | Protocatechualdehyde, formyl-14C-labeled | MeSH | 3,4-Dihydroxybenzaldehyde | HMDB | Protocatechualdehyde, 8CI | db_source |
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Predicted Properties | |
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Chemical Formula | C7H6O3 |
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IUPAC name | 3,4-dihydroxybenzaldehyde |
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InChI Identifier | InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H |
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InChI Key | IBGBGRVKPALMCQ-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=C(C=O)C=C1O |
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Average Molecular Weight | 138.1207 |
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Monoisotopic Molecular Weight | 138.031694058 |
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Classification |
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Description | Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl 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 | Hydroxybenzaldehydes |
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Alternative Parents | |
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Substituents | - Hydroxybenzaldehyde
- Catechol
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Organic oxide
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Role | Industrial application: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
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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 60.87%; H 4.38%; O 34.75% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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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 | [neutral] lmax 220 (e 9500) (95% EtOH) (Derep) | DFC |
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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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Predicted GC-MS | 3,4-Dihydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052r-2900000000-fd0d28650a72226166e6 | Spectrum | Predicted GC-MS | 3,4-Dihydroxybenzaldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00yi-8690000000-16ccc54dcf22361cffb1 | Spectrum | Predicted GC-MS | 3,4-Dihydroxybenzaldehyde, 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 - ESI-TOF 10V, Negative | splash10-0002-0040900010-522c055741661bbc5ba8 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0002-0040900010-522c055741661bbc5ba8 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0002-0040900010-522c055741661bbc5ba8 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-002r-0905000000-7987816fb8648b0eea18 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-000i-0900000000-aa91c9c469ec39450435 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-000i-0900000000-25b5b2bc87af9df04e91 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-000i-0900000000-03d9e2dbe57c9bcfb9ab | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-002r-0905000000-7987816fb8648b0eea18 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-000i-0900000000-aa91c9c469ec39450435 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-000i-0900000000-25b5b2bc87af9df04e91 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-aa91c9c469ec39450435 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-25b5b2bc87af9df04e91 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-db13978cfcbc33c6da32 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-1900000000-ed3a0258f14e4361b25c | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-9200000000-cdb54c91531419396213 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-db13978cfcbc33c6da32 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-1900000000-ed3a0258f14e4361b25c | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-9200000000-cdb54c91531419396213 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-882b8375384be94a3491 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1900000000-25b2a170eaf9dd74c4a0 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0kw4-9300000000-e349b638bc98dcdf0ade | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-882b8375384be94a3491 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1900000000-25b2a170eaf9dd74c4a0 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0kw4-9300000000-e349b638bc98dcdf0ade | 2015-05-27 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 723 |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | HCW75-Q:HCW75-Q |
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EAFUS ID | Not Available |
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Dr. Duke ID | PROTOCATECHUIC-ALDEHYDE|3,4-DIHYDROXYBENZALDEHYDE|PROTOCATECHUALDEHYDE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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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 | rw1040061 |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | 723 |
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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 | Descriptor | ID | Definition | Reference |
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anti aggregant | | | DUKE | anti coagulant | 50249 | An agent that prevents blood clotting. | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE |
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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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dry |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| medical |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| almond |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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). — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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