Record Information
Version1.0
Creation date2010-04-08 22:06:25 UTC
Update date2018-05-28 23:14:11 UTC
Primary IDFDB004830
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAzulene
DescriptionAzulene, also known as cyclopentacycloheptene or azulekeep, is a member of the class of compounds known as azulenes. Azulenes are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring. Azulene can be found in a number of food items such as anise, roman camomile, peppermint, and german camomile, which makes azulene a potential biomarker for the consumption of these food products. Azulene is a non-carcinogenic (not listed by IARC) potentially toxic compound. Azulene is an organic compound and an isomer of naphthalene. Whereas naphthalene is colourless, azulene is dark blue. Two terpenoids, vetivazulene (4,8-dimethyl-2-isopropylazulene) and guaiazulene (1,4-dimethyl-7-isopropylazulene), that feature the azulene skeleton are found in nature as constituents of pigments in mushrooms, guaiac wood oil, and some marine invertebrates . PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system (L10) (T3DB).
CAS Number275-51-4
Structure
Thumb
Synonyms
SynonymSource
AzulenChEBI
CyclopentacyclohepteneChEBI
AzulekeepMeSH
Azotesinbiospider
AZULENE, M.P. 99 Cbiospider
Azunamicbiospider
Azusalen [as sodium sulfonate]biospider
Bicyclo(0.3.5)deca-1,3,5,7,9-pentaenebiospider
Bicyclo(5.3.0)-1,3,5,7,9-decapentaenebiospider
BICYCLO(5.3.0)-DECA-2,4,6,8,10-PENTAENEbiospider
Bicyclo(5.3.0)decapentaenebiospider
Bicyclo[5.3.0]-1,3,5,7,9-decapentaenebiospider
Bicyclo[5.3.0]decapentaenebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP3.51ALOGPS
logP2.96ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.51 m³·mol⁻¹ChemAxon
Polarizability14.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H8
IUPAC nameazulene
InChI IdentifierInChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
InChI KeyCUFNKYGDVFVPHO-UHFFFAOYSA-N
Isomeric SMILESC1=CC2=CC=CC=CC2=C1
Average Molecular Weight128.1705
Monoisotopic Molecular Weight128.062600256
Classification
DescriptionThis compound belongs to the class of chemical entities known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassHydrocarbons
Sub ClassUnsaturated hydrocarbons
Direct ParentAzulenes
Alternative Parents
Substituents
  • Azulene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point99 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP3.20HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-c58668897462a120be2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-5a9b05b0e3abe8a17d1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-9435ad04abd5c7a3b5a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-878dba5e57117c17431dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-c732623515fe642c30afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-79c79d6e40451aba8b2dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-ddfe7244d5f01ca46998View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC13392
Pubchem Compound ID9231
Pubchem Substance IDNot Available
ChEBI ID31249
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDAZULENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
hepatoregenerative62868 Any compound that is able to prevent damage to the liver.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).