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Showing metabocard for Ethyl vanillin (HMDB0029665)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:54 UTC
Update Date2020-02-26 21:44:08 UTC
HMDB IDHMDB0029665
Secondary Accession Numbers
  • HMDB29665
Metabolite Identification
Common NameEthyl vanillin
DescriptionEthyl 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,.
Structure
Data?1582753448
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Ethoxy-4-formylphenolChEBI
3-EthoxyprotocatechualdehydeChEBI
4-Hydroxy-3-ethoxybenzaldehydeChEBI
BourbonalChEBI
Ethyl protalChEBI
VanilalChEBI
3-ETHOXY-4-hydroxy-benzaldehydeHMDB
3-Ethoxy-4-hydroxybenzaldehydeHMDB
AethylvanillinHMDB
EthavanHMDB
EthovanHMDB
Ethyl proto-catechualdehyde-3-ethyl etherHMDB
Ethyl protocatechualdehydeHMDB
Ethyl vanillin (NF)HMDB
Ethyl vanillin, usan?HMDB
Ethyl-vanillinHMDB
EthylprotalHMDB
Ethylprotocatechualdehyde-3-ethyl etherHMDB
Ethylprotocatechuic aldehydeHMDB
EthylvanillinHMDB
FEMA 2464HMDB
Protocatechuic aldehyde 3-ethyl etherHMDB
Protocatechuic aldehyde ethyl etherHMDB
QuantrovanilHMDB
Quantrovanil, vanillalHMDB
RhodiaromeHMDB
VanbeenolHMDB
VanillalHMDB
VaniromHMDB
VaniromeHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-ethoxy-4-hydroxybenzaldehyde
Traditional Nameethyl vanillin
CAS Registry Number121-32-4
SMILES
CCOC1=C(O)C=CC(C=O)=C1
InChI Identifier
InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3
InChI KeyCBOQJANXLMLOSS-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentHydroxybenzaldehydes
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point76 - 78 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.82 mg/mL at 25 °CNot Available
LogP1.58Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
logP1.82ALOGPS
logP1.58ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.79ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.83 m³·mol⁻¹ChemAxon
Polarizability17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-7900000000-82021b1b58fb03cd9cc6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-8900000000-120b162ff2c185f413bbSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-5cc4d780ed9e9279561dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-7900000000-82021b1b58fb03cd9cc6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-8900000000-120b162ff2c185f413bbSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-5cc4d780ed9e9279561dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0900000000-afc9dd7ed64604d0102fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4950000000-a33f56f4bc60325bef65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-89239990c4a10955d988Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1900000000-5c128876e8bad02cc839Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9700000000-bf41857855baca586fedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-6b1cd6daa42968b433bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1900000000-270e0adeb0ef058d650dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052s-9700000000-34282a16d387610767afSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID728
FooDB IDFDB000841
KNApSAcK IDNot Available
Chemspider ID8154
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthylvanillin
METLIN IDNot Available
PubChem Compound8467
PDB IDNot Available
ChEBI ID48408
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. DESHUSSES J, DESBAUMES P: [Paper chromatography of vanillin and ethylvanillin in food stuffs]. Mitt Geb Lebensmittelunters Hyg. 1957;48(2):49-58. [PubMed:13464725 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. WOGGON H, KOEHLER U: [Paper chromato-oscillopolarographic determination of vanillin and ethylvanillin in food]. Ernahrungsforsch Ber Mitt. 1960;5:402-9. [PubMed:13786183 ]
  9. PROFFT E, STEINKE U: [ON ETHYLVANILLIN. I]. Arch Pharm Ber Dtsch Pharm Ges. 1964 May;297:282-91. [PubMed:14243749 ]
  10. 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 ]
  11. HALD JG: [Detection of 2-alkoxyphenols in vanillin and ethylvanillin]. Dan Tidsskr Farm. 1961 Apr;35:73-7. [PubMed:13710686 ]
  12. 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 ]
  13. 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 ]
  14. PROFFT E, STEINKE U: [ON ETHYLVANILLIN. II]. Arch Pharm Ber Dtsch Pharm Ges. 1964 May;297:292-8. [PubMed:14243750 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .