Record Information
Version1.0
Creation date2010-04-08 22:13:06 UTC
Update date2019-11-26 03:14:54 UTC
Primary IDFDB017461
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRosmadial
DescriptionRosmadial belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Rosmadial is an extremely weak basic (essentially neutral) compound (based on its pKa). Rosmadial is found, on average, in the highest concentration within rosemaries. Rosmadial has also been detected, but not quantified in, several different foods, such as gingers, cumins, herbs and spices, caraway, and star anises. This could make rosmadial a potential biomarker for the consumption of these foods.
CAS Number85514-31-4
Structure
Thumb
Synonyms
SynonymSource
(-)-RosmadialHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.76ALOGPS
logP4.37ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability36.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H24O5
IUPAC name7-hydroxy-3',3'-dimethyl-2-oxo-6-(propan-2-yl)-2H-spiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde
InChI IdentifierInChI=1S/C20H24O5/c1-11(2)13-8-12(9-21)15-17(16(13)23)25-18(24)20(15)7-5-6-19(3,4)14(20)10-22/h8-11,14,23H,5-7H2,1-4H3
InChI KeyJBWRHBJFAVSAMJ-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2
Average Molecular Weight344.4016
Monoisotopic Molecular Weight344.162373878
Classification
Description belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Coumaran
  • Aryl-aldehyde
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.75%; H 7.02%; O 23.23%DFC
Melting PointMp 225°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D -216.8 (c, 0.54 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-0309000000-f623455987c2374d4235JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-2319800000-5ad28cbc5884f92494d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0209000000-968194b31f34fbdf2e7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hi2-3239000000-57a02ee126ff42746a02JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00o0-9802000000-557fab0dce37174b9809JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019000000-95758903e99ee99ca15aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0339000000-c956fea811809f0b7052JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03du-2932000000-ca31d768dd21e98e053bJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID670
DrugBank IDNot Available
HMDB IDHMDB38219
CRC / DFC (Dictionary of Food Compounds) IDKXS51-K:KXS51-K
EAFUS IDNot Available
Dr. Duke IDROSMADIAL
BIGG IDNot Available
KNApSAcK IDC00031190
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.
— 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.