Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2019-11-26 03:11:51 UTC
Primary IDFDB015565
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMatricin
DescriptionMatricin, also known as prochamazulene, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Matricin is an extremely weak basic (essentially neutral) compound (based on its pKa). Matricin has been detected, but not quantified in, several different foods, such as fats and oils, german camomiles, herbs and spices, and tea. This could make matricin a potential biomarker for the consumption of these foods.
CAS Number29041-35-8
Structure
Thumb
Synonyms
SynonymSource
ProchamazuleneHMDB
9-Hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,9H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acidGenerator
Matricindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP1.84ALOGPS
logP0.72ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.24ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.54 m³·mol⁻¹ChemAxon
Polarizability31.95 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H22O5
IUPAC name9-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate
InChI IdentifierInChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3
InChI KeySYTRJRUSWMMZLV-UHFFFAOYSA-N
Isomeric SMILESCC1C2C(OC1=O)C1C(C=CC1(C)O)=C(C)CC2OC(C)=O
Average Molecular Weight306.358
Monoisotopic Molecular Weight306.146723808
Classification
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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 66.65%; H 7.24%; O 26.11%DFC
Melting PointMp 158-160°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -131 (c, 1.96 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMatricin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0535-5190000000-1070f4e7e43c7456eb36Spectrum
Predicted GC-MSMatricin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014l-9168000000-bed017f2b316540fa06bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0092000000-b22be39f8ef1e5bb76b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-1390000000-4bedf6b02e8207bab105Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r5-2790000000-872223c58032fa25c2ccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0092000000-b22be39f8ef1e5bb76b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-1390000000-4bedf6b02e8207bab105Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r5-2790000000-872223c58032fa25c2ccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1096000000-cd74c6b9d2062e44c88dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-2091000000-303744d2fd1479b78ac6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-9760000000-b1a52ab2f5b5a9ac206fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1096000000-cd74c6b9d2062e44c88dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-2091000000-303744d2fd1479b78ac6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-9760000000-b1a52ab2f5b5a9ac206fSpectrum
NMRNot Available
ChemSpider ID2724149
ChEMBL IDNot Available
KEGG Compound IDC09499
Pubchem Compound ID3483298
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36643
CRC / DFC (Dictionary of Food Compounds) IDKDH68-H:KDH70-C
EAFUS IDNot Available
Dr. Duke IDMATRICIN
BIGG IDNot Available
KNApSAcK IDC00003321
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.