2-Isopropylphenol (T3D3945)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2014-08-12 17:09:46 UTC
Update Date2014-12-24 20:26:34 UTC
Accession NumberT3D3945
Identification
Common Name2-Isopropylphenol
ClassSmall Molecule
Description2-Isopropylphenol is a flavouring ingredient 2-isopropylphenol belongs to the family of Cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
Compound Type
  • Flavouring Agent
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1-Hydroxy-2-isopropylbenzene
1-Hydroxy-3-isopropylbenzene
2-(1-Methylethyl)-Phenol
2-(1-Methylethyl)phenol
2-(1-Methylethyl)phenol, 9CI
2-(Propan-2-yl)phenol
FEMA 3461
Isopropyl-Phenol
Isopropylphenol, ortho
O-Cumenol
O-Hydroxycumene
O-Isopropyl-Phenol
O-Isopropylphenol
Ortho-isopropylphenol
Prodox 131
Chemical FormulaC9H12O
Average Molecular Mass136.191 g/mol
Monoisotopic Mass136.089 g/mol
CAS Registry Number88-69-7
IUPAC Name2-(propan-2-yl)phenol
Traditional Name2-isopropylphenol
SMILESCC(C)C1=CC=CC=C1O
InChI IdentifierInChI=1S/C9H12O/c1-7(2)8-5-3-4-6-9(8)10/h3-7,10H,1-2H3
InChI KeyInChIKey=CRBJBYGJVIBWIY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCumenes
Direct ParentCumenes
Alternative Parents
Substituents
  • Phenylpropane
  • Cumene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point15 - 16°C
Boiling PointNot Available
SolubilityInsoluble
LogP2.88
Predicted Properties
PropertyValueSource
Water Solubility3.09 g/LALOGPS
logP2.78ALOGPS
logP2.91ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.5ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.23 m³·mol⁻¹ChemAxon
Polarizability15.63 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-9700000000-0a3ec6f0b6db49b1bb8c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-9700000000-0a3ec6f0b6db49b1bb8c2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-6900000000-65b25162f6cb1b887f172017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-8900000000-6f77c31ece141c6bd3232017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f27e4c86fd02f3a4d9f52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-7900000000-b30b63f3decaee02aa552016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9400000000-6296af1e3299f7217b192016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-69d37dcc656ad26252a02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-36ddf0e1e27114cf431a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-7900000000-512c84878dbff828e6bf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3d153ee27562ca42735c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0900000000-197285ccea74149669c92021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9100000000-8b244056e4ef8843629a2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9300000000-3a595b114a7498fb84702021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-6900000000-4dd9eeb2be33c550227c2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-66881aa4860995f95bad2021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-4900000000-0ab562a07073aa1cb86a2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32029
PubChem Compound ID6943
ChEMBL IDCHEMBL30018
ChemSpider ID6677
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID38506
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDIP0
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3945.pdf
General References
  1. Chiha M, Merouani S, Hamdaoui O, Baup S, Gondrexon N, Petrier C: Modeling of ultrasonic degradation of non-volatile organic compounds by Langmuir-type kinetics. Ultrason Sonochem. 2010 Jun;17(5):773-82. doi: 10.1016/j.ultsonch.2010.03.007. Epub 2010 Mar 27. [20388590 ]
  2. Toyama T, Momotani N, Ogata Y, Miyamori Y, Inoue D, Sei K, Mori K, Kikuchi S, Ike M: Isolation and characterization of 4-tert-butylphenol-utilizing Sphingobium fuliginis strains from Phragmites australis rhizosphere sediment. Appl Environ Microbiol. 2010 Oct;76(20):6733-40. doi: 10.1128/AEM.00258-10. Epub 2010 Aug 27. [20802076 ]
  3. Li J, Ma M, Wang Z: In vitro profiling of endocrine disrupting effects of phenols. Toxicol In Vitro. 2010 Feb;24(1):201-7. doi: 10.1016/j.tiv.2009.09.008. Epub 2009 Sep 16. [19765641 ]
  4. Toyama T, Maeda N, Murashita M, Chang YC, Kikuchi S: Isolation and characterization of a novel 2-sec-butylphenol-degrading bacterium Pseudomonas sp. strain MS-1. Biodegradation. 2010 Apr;21(2):157-65. doi: 10.1007/s10532-009-9290-y. Epub 2009 Aug 25. [19705287 ]
  5. Cho S, Choi Y, Park S, Park T: Carvacrol prevents diet-induced obesity by modulating gene expressions involved in adipogenesis and inflammation in mice fed with high-fat diet. J Nutr Biochem. 2012 Feb;23(2):192-201. doi: 10.1016/j.jnutbio.2010.11.016. Epub 2011 Mar 29. [21447440 ]
  6. Glenn GM, Klamczynski AP, Woods DF, Chiou B, Orts WJ, Imam SH: Encapsulation of plant oils in porous starch microspheres. J Agric Food Chem. 2010 Apr 14;58(7):4180-4. doi: 10.1021/jf9037826. [20196603 ]
  7. Shiizaki K, Asai S, Ebata S, Kawanishi M, Yagi T: Establishment of yeast reporter assay systems to detect ligands of thyroid hormone receptors alpha and beta. Toxicol In Vitro. 2010 Mar;24(2):638-44. doi: 10.1016/j.tiv.2009.10.001. Epub 2009 Oct 22. [19853653 ]
  8. Krcmar S: Responses of Tabanidae (Diptera) to canopy traps baited with 4-methylphenol, 3-isopropylphenol, and naphthalene. J Vector Ecol. 2007 Dec;32(2):188-92. [18260506 ]
  9. Harvey KA, Xu Z, Whitley P, Davisson VJ, Siddiqui RA: Characterization of anticancer properties of 2,6-diisopropylphenol-docosahexaenoate and analogues in breast cancer cells. Bioorg Med Chem. 2010 Mar 1;18(5):1866-74. doi: 10.1016/j.bmc.2010.01.045. Epub 2010 Jan 25. [20153203 ]
  10. Tsuchiya H, Ueno T, Tanaka T, Matsuura N, Mizogami M: Comparative study on determination of antioxidant and membrane activities of propofol and its related compounds. Eur J Pharm Sci. 2010 Jan 31;39(1-3):97-102. doi: 10.1016/j.ejps.2009.11.001. Epub 2009 Nov 6. [19897032 ]
  11. Leon I, Cocinero EJ, Millan J, Rijs AM, Usabiaga I, Lesarri A, Castano F, Fernandez JA: A combined spectroscopic and theoretical study of propofol.(H2O)3. J Chem Phys. 2012 Aug 21;137(7):074303. [22920116 ]
  12. Li J, Ma M, Wang Z: A two-hybrid yeast assay to quantify the effects of xenobiotics on retinoid X receptor-mediated gene expression. Toxicol Lett. 2008 Feb 15;176(3):198-206. doi: 10.1016/j.toxlet.2007.11.006. Epub 2007 Dec 3. [18207673 ]
  13. Feng Y, Colosi LM, Gao S, Huang Q, Mao L: Transformation and removal of tetrabromobisphenol A from water in the presence of natural organic matter via laccase-catalyzed reactions: reaction rates, products, and pathways. Environ Sci Technol. 2013 Jan 15;47(2):1001-8. doi: 10.1021/es302680c. Epub 2013 Jan 7. [23256593 ]
  14. Li J, Ma M, Wang Z: A two-hybrid yeast assay to quantify the effects of xenobiotics on thyroid hormone-mediated gene expression. Environ Toxicol Chem. 2008 Jan;27(1):159-67. [18092857 ]
  15. Alessio RJ, Li X, Martin DF: Removal of BPA model compounds and related substances by means of column chromatography using Octolig(R). J Environ Sci Health A Tox Hazard Subst Environ Eng. 2012;47(14):2198-204. doi: 10.1080/10934529.2012.707535. [22934990 ]
  16. Novak M, Brinster AM, Dickhoff JN, Erb JM, Jones MP, Leopold SH, Vollman AT, Wang YT, Glover SA: Chemistry of 4-alkylaryloxenium ion "precursors": sound and fury signifying something? J Org Chem. 2007 Dec 21;72(26):9954-62. Epub 2007 Nov 21. [18027966 ]
  17. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Androgen receptor
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
Target Details
2. Progesterone receptor
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da