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Record Information
Version3.6
Creation Date2012-09-11 20:47:14 UTC
Update Date2016-02-11 02:44:02 UTC
HMDB IDHMDB35766
Secondary Accession NumbersNone
Metabolite Identification
Common NameAscaridole
DescriptionAscaridole is found in cardamom. Said to be the major constituent of oil of Peumus boldus (boldo).Ascaridole is a natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is the primary constituent of the oil of Mexican Tea (Dysphania ambrosioides, formerly Chenopodium ambrosioides). It is a colorless liquid that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids. Ascaridole belongs to the family of Bicyclic Monoterpenes. These are monoterpenes containing exactly 2 rings, which are fused to each other.
Structure
Thumb
Synonyms
ValueSource
1,4-Epidioxy-P-menth-2-eneChEBI
1,4-peroxido-P-Menthene-2ChEBI
1,4-Peroxy-P-menth-2-eneChEBI
1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-eneChEBI
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-eneChEBI
1, 4-Epidioxy-P-menth-2-eneHMDB
1, 4-Peroxy-P-menth-2-eneHMDB
1,4-Epidioxy-2-P-mentheneHMDB
1-Isopropyl-4-methyl-2,3-dioxabicyclo(2.2.2)oct-5-eneHMDB
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]hept-2-eneHMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-eneHMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9ciHMDB
4-Methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-eneHMDB
AscapurinHMDB
AscaricumHMDB
AscaridiolHMDB
AscaridolHMDB
Ascaridole (organic peroxide)HMDB
Ascaridole epoxideHMDB
AscarisinHMDB
AskaridolHMDB
cis-AscaridoleHMDB
Kebal IIHMDB
UncinacinaHMDB
Chemical FormulaC10H16O2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
IUPAC Name1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
Traditional Nameascaridole
CAS Registry Number512-85-6
SMILES
CC(C)C12CCC(C)(OO1)C=C2
InChI Identifier
InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3
InChI KeyInChIKey=MGYMHQJELJYRQS-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Laboratory Chemical
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point3.3 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.53 mg/mLALOGPS
logP2.64ALOGPS
logP2.64ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.6 m3·mol-1ChemAxon
Polarizability18.93 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014503
KNApSAcK IDC00003027
Chemspider ID10105
KEGG Compound IDC09836
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAscaridole
NuGOwiki LinkHMDB35766
Metagene LinkHMDB35766
METLIN IDNot Available
PubChem Compound10545
PDB IDNot Available
ChEBI ID2866
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.