2-ISOPROPYLPHENOL

Relevant Data

Food Additives Approved in the United States

Flavouring Substances Approved by European Union:

  • 2-Isopropylphenol [show]

General Information

Synonyms: o-CUMENOL, 1-HYDROXY-2-ISOPROPYLBENZENE
Chemical Names: 2-ISOPROPYLPHENOL
CAS number: 88-69-7
COE number: 11234
JECFA number: 697
FEMA number: 3461
Functional Class: Flavouring Agent
FLAVOURING_AGENT

From apps.who.int

Evaluations

Evaluation year: 2000
ADI: No safety concern at current levels of intake when used as a flavouring agent
Report: TRS 901-JECFA 55/44
Tox Monograph: FAS 46-JECFA 55/165
Specification: COMPENDIUM ADDENDUM 8/FNP 52 Add.8/168

From apps.who.int

Computed Descriptors

Download SDF
2D Structure
CID6943
IUPAC Name2-propan-2-ylphenol
InChIInChI=1S/C9H12O/c1-7(2)8-5-3-4-6-9(8)10/h3-7,10H,1-2H3
InChI KeyCRBJBYGJVIBWIY-UHFFFAOYSA-N
Canonical SMILESCC(C)C1=CC=CC=C1O
Molecular FormulaC9H12O
Wikipedia2-isopropylphenol

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight136.194
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Complexity98.9
CACTVS Substructure Key Fingerprint A A A D c c B w I A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D Q S A m A A y B o A A A g C A A i B C A A A C A A A g I A A I i A A G C I g I J i K C E R K A c A A k w B E I m A e A w O A O g A A A A A A I A A A A A A A A A B A A A A A A A A A A A A = =
Topological Polar Surface Area20.2
Monoisotopic Mass136.089
Exact Mass136.089
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9343
Human Intestinal AbsorptionHIA+0.9959
Caco-2 PermeabilityCaco2+0.9252
P-glycoprotein SubstrateNon-substrate0.7169
P-glycoprotein InhibitorNon-inhibitor0.9517
Non-inhibitor0.9918
Renal Organic Cation TransporterNon-inhibitor0.8924
Distribution
Subcellular localizationMitochondria0.8571
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7475
CYP450 2D6 SubstrateSubstrate0.5916
CYP450 3A4 SubstrateNon-substrate0.6106
CYP450 1A2 InhibitorInhibitor0.8772
CYP450 2C9 InhibitorNon-inhibitor0.8617
CYP450 2D6 InhibitorNon-inhibitor0.9371
CYP450 2C19 InhibitorNon-inhibitor0.8519
CYP450 3A4 InhibitorNon-inhibitor0.9310
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7533
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9056
Non-inhibitor0.9162
AMES ToxicityNon AMES toxic0.9268
CarcinogensNon-carcinogens0.7631
Fish ToxicityHigh FHMT0.8751
Tetrahymena Pyriformis ToxicityHigh TPT0.9134
Honey Bee ToxicityHigh HBT0.8059
BiodegradationNot ready biodegradable0.5908
Acute Oral ToxicityIII0.7729
Carcinogenicity (Three-class)Non-required0.7231

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-1.5549LogS
Caco-2 Permeability1.7563LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4324LD50, mol/kg
Fish Toxicity0.6634pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6902pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure
Mechanism of Toxicity
Metabolism
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level
Health Effects
Treatment
Reference
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  2. 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 ]
  3. 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 ]
  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 ]
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  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 ]
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  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 ]
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From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassCumenes
Intermediate Tree NodesNot available
Direct ParentCumenes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenylpropane - Cumene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.

From ClassyFire

Targets

Target Details

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

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

From T3DB