Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2019-11-26 03:11:52 UTC
Primary IDFDB015573
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7-Isopropyl-1,4-dimethylazulene
Description7-Isopropyl-1,4-dimethylazulene, also known as 1,4-dimethyl-7-isopropylazulene or guaiazulene, belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Thus, 7-isopropyl-1,4-dimethylazulene is considered to be an isoprenoid lipid molecule. 7-Isopropyl-1,4-dimethylazulene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number489-84-9
Structure
Thumb
Synonyms
SynonymSource
1,4-Dimethyl-7-(1-methylethyl)azuleneChEBI
1,4-Dimethyl-7-isopropylazuleneChEBI
3,8-Dimethyl-5-(2-propyl)azuleneChEBI
GuaiazuleneKegg
AzunolKegg
1, 4-Dimethyl-7-isopropylazuleneHMDB
1,3,5,7,9-GuaiapentaeneHMDB
1,4-Dimethyl-7-(1-methyl)-azulene (azulon)HMDB
1,4-Dimethyl-7-(1-methylethyl)-azuleneHMDB
1,4-Dimethyl-7-(1-methylethyl)azulene, 9ciHMDB
1,4-Dimethyl-7-(propan-2-yl)azuleneHMDB
1,4-Dimethyl-7-isopropyl-azuleneHMDB
7-Isopropyl- 1,4-dimethylazuleneHMDB
7-Isopropyl-1,4-dimethyl-azuleneHMDB
AZ-8 berisHMDB
Azulen-berisHMDB
Azulene, 7-isopropyl-1,4-dimethyl- (8ci)HMDB
AzulolHMDB
AzulonHMDB
CuteazulHMDB
EucazulenHMDB
EucazuleneHMDB
GuajazuleneHMDB
GuiazuleneHMDB
GurjunazulenHMDB
HepatoprotectantHMDB
KessazulenHMDB
KessazuleneHMDB
PurazulenHMDB
S-GuaiazuleneHMDB
SilazulonHMDB
UroazulenHMDB
VaumiganHMDB
VetivazulenHMDB
7-Isopropyl-1,4-dimethylazuleneChEBI
1,4-dimethyl-7-(1-methyl)-azulene (azulon)biospider
1,4-Dimethyl-7-(1-methylethyl)azulene, 9CIdb_source
1,4-dimethyl-7-(propan-2-yl)azulenebiospider
1,4-Dimethyl-7-isopropylazulene (JAN)biospider
7-isopropyl- 1,4-dimethylazulenebiospider
Azulene, 1,4-dimethyl-7-(1-methylethyl)-biospider
Azulene, 1,4-dimethyl-7-isopropyl-biospider
Azulene, 7-isopropyl-1, 4-dimethyl-biospider
Azulene, 7-isopropyl-1,4-dimethyl-biospider
Azulene, 7-isopropyl-1,4-dimethyl- (8CI)biospider
Azunol (TN)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP4.99ALOGPS
logP5.23ChemAxon
logS-3.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.78 m³·mol⁻¹ChemAxon
Polarizability25.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H18
IUPAC name1,4-dimethyl-7-(propan-2-yl)azulene
InChI IdentifierInChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
InChI KeyFWKQNCXZGNBPFD-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=CC2=C(C)C=CC2=C(C)C=C1
Average Molecular Weight198.3034
Monoisotopic Molecular Weight198.140850576
Classification
Description belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGuaianes
Alternative Parents
Substituents
  • Guaiane sesquiterpenoid
  • Azulene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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 90.85%; H 9.15%DFC
Melting PointMp 31.5°DFC
Boiling PointBp12 167-168°DFC
Experimental Water Solubility0.000664 mg/mL at 25 oCREZA, J et al. (2002)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data632 () (Et2O)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-1900000000-be4c0960d06735436fe8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-3339d5b27a9967e9c5daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-44d06797d9da8aaae9dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-1900000000-6fe86a22e14c459ce6d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-48f7566ceaa93d43c699JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-ee4c5f9ee7e99d6db7ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o1-1900000000-e4e77ed98ea343b05eb3JSpectraViewer
ChemSpider ID3395
ChEMBL IDCHEMBL1408759
KEGG Compound IDC09675
Pubchem Compound ID3515
Pubchem Substance IDNot Available
ChEBI ID5550
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36648
CRC / DFC (Dictionary of Food Compounds) IDKDJ01-S:KDJ01-S
EAFUS IDNot Available
Dr. Duke IDGUAIAZULENE
BIGG IDNot Available
KNApSAcK IDC00003138
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
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leprotic33282 A substance that kills or slows the growth of bacteria.DUKE
anti pepticDUKE
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 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
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.