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Showing Compound Proazulene (FDB006586)

Record Information
Version1.0
Creation date2010-04-08 22:07:12 UTC
Update date2019-11-26 03:01:12 UTC
Primary IDFDB006586
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProazulene
DescriptionProazulene, also known as matricine, is a member of the class of 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. Thus, proazulene is considered to be an isoprenoid lipid molecule. Proazulene is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proazulene can be found in anise, which makes proazulene a potential biomarker for the consumption of this food product. Chamazulene, a blue-violet derivative of azulene, found in a variety of plants including in chamomile (Matricaria chamomilla), wormwood (Artemisia absinthium) and yarrow (Achillea millefolium) is biosynthesized from matricin .
CAS Number29041-35-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
Polarizability32.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H22O5
IUPAC name(3S,3aR,4S,9R,9aS,9bS)-9-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/t9-,12-,13+,14-,15-,17+/m0/s1
InChI KeySYTRJRUSWMMZLV-VQGWEXQJSA-N
Isomeric SMILES[H][C@@]1(C)C(=O)O[C@]2([H])[C@]3([H])C(C=C[C@@]3(C)O)=C(C)C[C@]([H])(OC(C)=O)[C@@]12[H]
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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0092000000-c32cc1287a034b6e5db22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-1390000000-0b9da7cd88a6f9e73a152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r2-2690000000-c6d6734ac18e662c88412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1096000000-71fbf65a74d14def241a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-2091000000-3927878b52c3ea79c29a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-9760000000-1f4c46abbecf2611552e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-cad28caa46734f0d543d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0090000000-8ea33f139e18a7766ddc2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-7960000000-75a47a79a386351ec33a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4039000000-8af4fae6f4ea04d446d22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9010000000-83c235754eddd3bf99152021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-9a2b148e582e57f23abd2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPROAZULENE
BIGG IDNot Available
KNApSAcK IDNot Available
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
AniseExpected but not quantifiedNot AvailableDUKE
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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).