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Showing Compound 4-Hydroxy-3,5-dimethoxybenzaldehyde (FDB000822)

Record Information
Version1.0
Creation date2010-04-08 22:04:43 UTC
Update date2019-11-26 02:55:28 UTC
Primary IDFDB000822
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxy-3,5-dimethoxybenzaldehyde
Description4-hydroxy-3,5-dimethoxybenzaldehyde, also known as sinapaldehyde or 2,6-dimethoxy-4-formylphenol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-hydroxy-3,5-dimethoxybenzaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-hydroxy-3,5-dimethoxybenzaldehyde is a mild, sweet, and plastic tasting compound and can be found in a number of food items such as whisky, common grape, garden tomato (variety), and coriander, which makes 4-hydroxy-3,5-dimethoxybenzaldehyde a potential biomarker for the consumption of these food products. 4-hydroxy-3,5-dimethoxybenzaldehyde may be a unique S.cerevisiae (yeast) metabolite. Because it contains many functional groups, it can be classified in many ways - aromatic, aldehyde, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in alcohol and polar organic solvents. Its refractive index is 1.53 .
CAS Number134-96-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
SinapaldehydeChEMBL
SYALMeSH
2,6-Dimethoxy-4-formylphenolMeSH
3,5-Dimethoxy-4-hydroxybenzaldehydeMeSH
4-Hydroxy-3,5-dimethoxybenzaldehydePhytoBank
4-Formyl-2,6-dimethoxyphenolPhytoBank
4-FormylsyringolPhytoBank
Cedar aldehydePhytoBank
Gallaldehyde 3,5-dimethyl etherPhytoBank
Syringic aldehydePhytoBank
3,5-Dimethoxy-4-hydroxy-benzaldehydePhytoBank
3,5-Dimethoxy-4-Hydroxy-Benzaldehydebiospider
3,5-DIMETHOXY-4-HYDROXYBENZALDEHYDE, PUREbiospider
3,5-Dimethoxy-4-hydroxybenzene carbonalbiospider
4-Hydroksy-3,5-dwumetoksybenzaldehydbiospider
4-Hydroxy-3,5-dimethoxybenzaldehyde (syringaldehyde)biospider
4-hydroxy-3,5-methoxybenzaldehydebiospider
Benzaldehyde, 3,5-dimethoxy-4-hydroxy-biospider
Benzaldehyde, 4-hydroxy-3,5-dimethoxy-biospider
Siringic aldehydebiospider
Syringaaldehydebiospider
Syringaldehydedb_source
Syringe aldehydebiospider
Syringealdehydebiospider
Syringylaldehydebiospider
Predicted Properties
PropertyValueSource
Water Solubility3.68 g/LALOGPS
logP1.33ALOGPS
logP1.07ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)7.24ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability17.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O4
IUPAC name4-hydroxy-3,5-dimethoxybenzaldehyde
InChI IdentifierInChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
InChI KeyKCDXJAYRVLXPFO-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(C=O)=CC(OC)=C1O
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
Classification
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Hydroxybenzaldehyde
  • Anisole
  • Benzaldehyde
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Aryl-aldehyde
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.34%; H 5.53%; O 35.13%DFC
Melting PointMp 113-114°DFC
Boiling PointBp14 192-193°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data368 (e 25100) (MeOH/NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-5900000000-6cbbbdbec8f6bba463d52015-03-01View Spectrum
Predicted GC-MS4-Hydroxy-3,5-dimethoxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-0900000000-ef96b9e519092161a3cbSpectrum
Predicted GC-MS4-Hydroxy-3,5-dimethoxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxy-3,5-dimethoxybenzaldehyde, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxy-3,5-dimethoxybenzaldehyde, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-9100000000-5b6ba3c42dcd3af29af02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-002b-9500000000-59dc9fbf56278b4fa3d72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00or-9000000000-7fdf6c97fc44ba9287572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-05gi-0900000000-44ca2aac27277cc862f52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-002b-9500000000-648b4cea88c99f6001802021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-05gi-0900000000-ec8dfff58a288a3a22022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-9100000000-54826f5ed4bf4c6506782021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00or-9000000000-03822b23e64682ed88792021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-888409d99d78544d7bda2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-9a08dd0b4c0aa032b8212016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hhi-3900000000-9de8232d167c5c3dc77e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-9ff54d007d617002d7302016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-5756b0978ed9c9206dfc2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0671-5900000000-61166ea22e1f8c56bc122016-08-04View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, DMSO, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, DMSO, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID8655
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID722
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBJH89-J:BJH96-J
EAFUS ID1742
Dr. Duke IDSYRINGALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00007558
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1026801
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti edemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 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
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
plastic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tonka
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.