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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:21 UTC

Update Date

2023-02-21 17:21:30 UTC

HMDB ID

HMDB0032029

Secondary Accession Numbers

HMDB32029

Metabolite Identification

Common Name

2-Isopropylphenol

Description

2-Isopropylphenol, also known as O-cumenol or O-hydroxycumene, belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. 2-Isopropylphenol is a creosote, medicinal, and phenolic tasting compound. Based on a literature review a significant number of articles have been published on 2-Isopropylphenol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Hydroxy-2-isopropylbenzene	ChEBI
2-(1-Methylethyl)phenol	ChEBI
O-Cumenol	ChEBI
O-Hydroxycumene	ChEBI
O-Isopropylphenol	ChEBI
Ortho-isopropylphenol	MeSH
1-Hydroxy-3-isopropylbenzene	HMDB
2-(1-Methylethyl)-phenol	HMDB
2-(1-Methylethyl)phenol, 9ci	HMDB
2-(Propan-2-yl)phenol	HMDB
FEMA 3461	HMDB
Isopropyl-phenol	HMDB
Isopropylphenol, ortho	HMDB
O-Isopropyl-phenol	HMDB
Prodox 131	HMDB

Chemical Formula

C₉H₁₂O

Average Molecular Weight

136.191

Monoisotopic Molecular Weight

136.088815006

IUPAC Name

2-(propan-2-yl)phenol

Traditional Name

2-isopropylphenol

CAS Registry Number

88-69-7

SMILES

CC(C)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C9H12O/c1-7(2)8-5-3-4-6-9(8)10/h3-7,10H,1-2H3

InChI Key

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Cumenes

Direct Parent

Cumenes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:38506 )

Ontology

Cellular substructure

Membrane (HMDB: HMDB0032029)
Cell membrane (HMDB: HMDB0032029)

Source

Endogenous

Endogenous (HMDB: HMDB0032029)

Exogenous

Food

Food (HMDB: HMDB0032029)

Exogenous (HMDB: HMDB0032029)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032029)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	15 - 16 °C	Not Available
Boiling Point	212.00 to 214.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1146 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.88	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.09 g/L	ALOGPS
logP	2.78	ALOGPS
logP	2.91	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	10.5	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.23 m³·mol⁻¹	ChemAxon
Polarizability	15.63 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.253	31661259
DarkChem	[M-H]-	125.862	31661259
DeepCCS	[M+H]+	133.822	30932474
DeepCCS	[M-H]-	131.577	30932474
DeepCCS	[M-2H]-	167.909	30932474
DeepCCS	[M+Na]+	142.777	30932474
AllCCS	[M+H]+	126.5	32859911
AllCCS	[M+H-H2O]+	121.8	32859911
AllCCS	[M+NH4]+	130.9	32859911
AllCCS	[M+Na]+	132.2	32859911
AllCCS	[M-H]-	127.9	32859911
AllCCS	[M+Na-2H]-	129.7	32859911
AllCCS	[M+HCOO]-	131.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Isopropylphenol	CC(C)C1=CC=CC=C1O	2050.1	Standard polar	33892256
2-Isopropylphenol	CC(C)C1=CC=CC=C1O	1143.7	Standard non polar	33892256
2-Isopropylphenol	CC(C)C1=CC=CC=C1O	1199.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Isopropylphenol,1TMS,isomer #1	CC(C)C1=CC=CC=C1O[Si](C)(C)C	1237.4	Semi standard non polar	33892256
2-Isopropylphenol,1TBDMS,isomer #1	CC(C)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	1468.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Isopropylphenol EI-B (Non-derivatized)	splash10-00dr-9700000000-0a3ec6f0b6db49b1bb8c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Isopropylphenol EI-B (Non-derivatized)	splash10-00dr-9700000000-0a3ec6f0b6db49b1bb8c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isopropylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-6900000000-65b25162f6cb1b887f17	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isopropylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-8900000000-6f77c31ece141c6bd323	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isopropylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-4900000000-0ab562a07073aa1cb86a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 10V, Positive-QTOF	splash10-000i-0900000000-f27e4c86fd02f3a4d9f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 20V, Positive-QTOF	splash10-000i-7900000000-b30b63f3decaee02aa55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 40V, Positive-QTOF	splash10-0uxu-9400000000-6296af1e3299f7217b19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 10V, Negative-QTOF	splash10-000i-0900000000-69d37dcc656ad26252a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 20V, Negative-QTOF	splash10-000i-0900000000-36ddf0e1e27114cf431a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 40V, Negative-QTOF	splash10-00ku-7900000000-512c84878dbff828e6bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 10V, Negative-QTOF	splash10-000i-0900000000-3d153ee27562ca42735c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 20V, Negative-QTOF	splash10-0019-0900000000-197285ccea74149669c9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 40V, Negative-QTOF	splash10-014l-9100000000-8b244056e4ef8843629a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 10V, Positive-QTOF	splash10-0002-9300000000-3a595b114a7498fb8470	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 20V, Positive-QTOF	splash10-00ku-6900000000-4dd9eeb2be33c550227c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropylphenol 40V, Positive-QTOF	splash10-00mo-9000000000-66881aa4860995f95bad	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008729

KNApSAcK ID

C00010968

Chemspider ID

6677

KEGG Compound ID

Not Available

BioCyc ID

CPD-14150

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6943

PDB ID

IP0

ChEBI ID

38506

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036321

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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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. [PubMed:19765641 ]
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. [PubMed:19705287 ]
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. [PubMed:21447440 ]
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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. [PubMed:19853653 ]
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. [PubMed:18260506 ]
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. [PubMed:20153203 ]
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. [PubMed:19897032 ]
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. [PubMed:22920116 ]
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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. [PubMed:23256593 ]
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. [PubMed:18092857 ]
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Showing metabocard for 2-Isopropylphenol (HMDB0032029)

MOL for HMDB0032029 (2-Isopropylphenol)

3D MOL for HMDB0032029 (2-Isopropylphenol)

3D SDF for HMDB0032029 (2-Isopropylphenol)

3D-SDF for HMDB0032029 (2-Isopropylphenol)

PDB for HMDB0032029 (2-Isopropylphenol)

3D PDB for HMDB0032029 (2-Isopropylphenol)

SMILES for HMDB0032029 (2-Isopropylphenol)

INCHI for HMDB0032029 (2-Isopropylphenol)

Structure for HMDB0032029 (2-Isopropylphenol)

3D Structure for HMDB0032029 (2-Isopropylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra