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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:31:54 UTC |
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Update Date | 2020-02-26 21:44:08 UTC |
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HMDB ID | HMDB0029665 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ethyl vanillin |
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Description | Ethyl vanillin, also known as ethyl protal or bourbonal, 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. Ethyl vanillin is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl vanillin is a sweet, caramel, and creamy tasting compound. Outside of the human body,. |
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Structure | |
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Synonyms | Value | Source |
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2-Ethoxy-4-formylphenol | ChEBI | 3-Ethoxyprotocatechualdehyde | ChEBI | 4-Hydroxy-3-ethoxybenzaldehyde | ChEBI | Bourbonal | ChEBI | Ethyl protal | ChEBI | Vanilal | ChEBI | 3-ETHOXY-4-hydroxy-benzaldehyde | HMDB | 3-Ethoxy-4-hydroxybenzaldehyde | HMDB | Aethylvanillin | HMDB | Ethavan | HMDB | Ethovan | HMDB | Ethyl proto-catechualdehyde-3-ethyl ether | HMDB | Ethyl protocatechualdehyde | HMDB | Ethyl vanillin (NF) | HMDB | Ethyl vanillin, usan? | HMDB | Ethyl-vanillin | HMDB | Ethylprotal | HMDB | Ethylprotocatechualdehyde-3-ethyl ether | HMDB | Ethylprotocatechuic aldehyde | HMDB | Ethylvanillin | HMDB | FEMA 2464 | HMDB | Protocatechuic aldehyde 3-ethyl ether | HMDB | Protocatechuic aldehyde ethyl ether | HMDB | Quantrovanil | HMDB | Quantrovanil, vanillal | HMDB | Rhodiarome | HMDB | Vanbeenol | HMDB | Vanillal | HMDB | Vanirom | HMDB | Vanirome | HMDB |
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Chemical Formula | C9H10O3 |
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Average Molecular Weight | 166.1739 |
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Monoisotopic Molecular Weight | 166.062994186 |
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IUPAC Name | 3-ethoxy-4-hydroxybenzaldehyde |
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Traditional Name | ethyl vanillin |
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CAS Registry Number | 121-32-4 |
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SMILES | CCOC1=C(O)C=CC(C=O)=C1 |
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InChI Identifier | InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 |
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InChI Key | CBOQJANXLMLOSS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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
- Phenoxy compound
- Phenol ether
- Benzoyl
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Benzenoid
- Monocyclic benzene moiety
- Ether
- 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 | Source: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 76 - 78 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 2.82 mg/mL at 25 °C | Not Available | LogP | 1.58 | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-7900000000-82021b1b58fb03cd9cc6 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-8900000000-120b162ff2c185f413bb | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-4900000000-5cc4d780ed9e9279561d | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-7900000000-82021b1b58fb03cd9cc6 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-8900000000-120b162ff2c185f413bb | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-4900000000-5cc4d780ed9e9279561d | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-0900000000-afc9dd7ed64604d0102f | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-4950000000-a33f56f4bc60325bef65 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-89239990c4a10955d988 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014r-1900000000-5c128876e8bad02cc839 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fu-9700000000-bf41857855baca586fed | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-6b1cd6daa42968b433bc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014r-1900000000-270e0adeb0ef058d650d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052s-9700000000-34282a16d387610767af | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | 728 |
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FooDB ID | FDB000841 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8154 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Ethylvanillin |
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METLIN ID | Not Available |
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PubChem Compound | 8467 |
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PDB ID | Not Available |
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ChEBI ID | 48408 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - CAUJOLLE F, MEYNIER D: [Effects of vanillin, orthovanillin, ethylvanillin and their corresponding dialdehydes on smooth muscle fibers]. Ann Pharm Fr. 1954 Jun;12(6):448-58. [PubMed:13229068 ]
- Shimada M, Habe T, Umezawa T, Higuchi T, Okamoto T: The C-C bond cleavage of a lignin model compound, 1,2-diarylpropane-1,3-diol, with a heme-enzyme model catalyst tetraphenylporphyrinatoiron(III)chloride in the presence of tert-butylhydroperoxide. Biochem Biophys Res Commun. 1984 Aug 16;122(3):1247-52. [PubMed:6477560 ]
- DESHUSSES J, DESBAUMES P: [Paper chromatography of vanillin and ethylvanillin in food stuffs]. Mitt Geb Lebensmittelunters Hyg. 1957;48(2):49-58. [PubMed:13464725 ]
- Sasaki YuF, Imanishi H, Ohta T, Shirasu Y: Effects of antimutagenic flavourings on SCEs induced by chemical mutagens in cultured Chinese hamster cells. Mutat Res. 1987 Nov;189(3):313-8. [PubMed:3670335 ]
- Jansson T, Curvall M, Hedin A, Enzell CR: In vitro studies of the biological effects of cigarette smoke condensate. III. Induction of SCE by some phenolic and related constituents derived from cigarette smoke. A study of structure-activity relationships. Mutat Res. 1988 Sep;206(1):17-24. [PubMed:3412370 ]
- CAUJOLLE F, MEYNIER D: [Toxicity of vanillin, o-vanillin, ethylvanillin and the corresponding isophthalaldehydes]. Ann Pharm Fr. 1954 Jan;12(1):42-9. [PubMed:13171720 ]
- Fujioka K, Shibamoto T: Improved malonaldehyde assay using headspace solid-phase microextraction and its application to the measurement of the antioxidant activity of phytochemicals. J Agric Food Chem. 2005 Jun 15;53(12):4708-13. [PubMed:15941304 ]
- WOGGON H, KOEHLER U: [Paper chromato-oscillopolarographic determination of vanillin and ethylvanillin in food]. Ernahrungsforsch Ber Mitt. 1960;5:402-9. [PubMed:13786183 ]
- PROFFT E, STEINKE U: [ON ETHYLVANILLIN. I]. Arch Pharm Ber Dtsch Pharm Ges. 1964 May;297:282-91. [PubMed:14243749 ]
- Timotheou-Potamia M, Calokerinos AC: Chemiluminometric determination of vanillin in commercial vanillin products. Talanta. 2007 Jan 15;71(1):208-12. doi: 10.1016/j.talanta.2006.03.046. Epub 2006 Jun 19. [PubMed:19071290 ]
- HALD JG: [Detection of 2-alkoxyphenols in vanillin and ethylvanillin]. Dan Tidsskr Farm. 1961 Apr;35:73-7. [PubMed:13710686 ]
- Kahoun D, Rezkova S, Veskrnova K, Kralovsky J, Holcapek M: Determination of phenolic compounds and hydroxymethylfurfural in meads using high performance liquid chromatography with coulometric-array and UV detection. J Chromatogr A. 2008 Aug 15;1202(1):19-33. doi: 10.1016/j.chroma.2008.06.016. Epub 2008 Jun 18. [PubMed:18620360 ]
- Lima DL, Duarte AC, Esteves VI: Optimization of phenolic compounds analysis by capillary electrophoresis. Talanta. 2007 Jun 15;72(4):1404-9. doi: 10.1016/j.talanta.2007.01.049. Epub 2007 Jan 30. [PubMed:19071776 ]
- PROFFT E, STEINKE U: [ON ETHYLVANILLIN. II]. Arch Pharm Ber Dtsch Pharm Ges. 1964 May;297:292-8. [PubMed:14243750 ]
- Zech M, Glaser B: Compound-specific delta18O analyses of neutral sugars in soils using gas chromatography-pyrolysis-isotope ratio mass spectrometry: problems, possible solutions and a first application. Rapid Commun Mass Spectrom. 2009 Nov;23(22):3522-32. doi: 10.1002/rcm.4278. [PubMed:19844972 ]
- Ohta T, Watanabe M, Watanabe K, Shirasu Y, Kada T: Inhibitory effects of flavourings on mutagenesis induced by chemicals in bacteria. Food Chem Toxicol. 1986 Jan;24(1):51-4. [PubMed:3512393 ]
- Rhee YS, Shin YH, Park CW, Chi SC, Park ES: Effect of flavors on the viscosity and gelling point of aqueous poloxamer solution. Arch Pharm Res. 2006 Dec;29(12):1171-8. [PubMed:17225469 ]
- Cocinero EJ, Lesarri A, Ecija P, Grabow JU, Fernandez JA, Castano F: Conformational equilibria in vanillin and ethylvanillin. Phys Chem Chem Phys. 2010 Oct 21;12(39):12486-93. doi: 10.1039/c0cp00585a. Epub 2010 Aug 19. [PubMed:20721403 ]
- Ohashi M, Omae H, Hashida M, Sowa Y, Imai S: Determination of vanillin and related flavor compounds in cocoa drink by capillary electrophoresis. J Chromatogr A. 2007 Jan 5;1138(1-2):262-7. Epub 2006 Nov 7. [PubMed:17084851 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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