4,4'-Dihydroxy-5,5'-diisopropyl-2,2'-dimethyl-3,6-biphenyldione (CHEM033903)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:31:11 UTC
Update Date2016-11-09 01:21:01 UTC
Accession NumberCHEM033903
Identification
Common Name4,4'-Dihydroxy-5,5'-diisopropyl-2,2'-dimethyl-3,6-biphenyldione
ClassSmall Molecule
Description4,4'-Dihydroxy-5,5'-diisopropyl-2,2'-dimethyl-3,6-biphenyldione is found in herbs and spices. 4,4'-Dihydroxy-5,5'-diisopropyl-2,2'-dimethyl-3,6-biphenyldione is a constituent of the leaves of thyme Thymus vulgaris. Shows antioxidant activity.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC20H24O4
Average Molecular Mass328.402 g/mol
Monoisotopic Mass328.167 g/mol
CAS Registry Number120866-14-0
IUPAC Name2-hydroxy-5-[4-hydroxy-2-methyl-5-(propan-2-yl)phenyl]-6-methyl-3-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
Traditional Name2-hydroxy-5-(4-hydroxy-5-isopropyl-2-methylphenyl)-3-isopropyl-6-methylcyclohexa-2,5-diene-1,4-dione
SMILESCC(C)C1=C(O)C=C(C)C(=C1)C1=C(C)C(=O)C(O)=C(C(C)C)C1=O
InChI IdentifierInChI=1S/C20H24O4/c1-9(2)13-8-14(11(5)7-15(13)21)17-12(6)18(22)20(24)16(10(3)4)19(17)23/h7-10,21,24H,1-6H3
InChI KeyLCYBFRVRIDYNSS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPrenylquinones
Alternative Parents
Substituents
  • Prenylbenzoquinone
  • P-cymene
  • Aromatic monoterpenoid
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Cumene
  • Phenylpropane
  • Quinone
  • P-benzoquinone
  • M-cresol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Enol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP3.52ALOGPS
logP5.15ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.39ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.52 m³·mol⁻¹ChemAxon
Polarizability36.57 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0i00-2295000000-1ed9195cf118d78bc18fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2162900000-54df8960d8a56c75e75bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0119000000-c9cd45cee6d58a6eaf57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hkj-2797000000-89b0aac1d5bea8143f26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06s9-2910000000-80bab0f14cfd6b4b992fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-21a75791e97e4c8f264cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2397000000-b200e75e967eeb684406Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-6962000000-90a322e49388e52f78d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-11018b6b6beac12e5f07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0096000000-e6c1068154488b16cc47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-090a-2910000000-03ef53d619a0d86580d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-fd417bc7f7b273e09154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0139000000-9538fda58e3b459bf9e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05pk-2391000000-7a0cbce9a5dcaef7c259Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0040760
FooDB IDFDB020576
Phenol Explorer IDNot Available
KNApSAcK IDC00056646
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30777508
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM