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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:17 UTC

Update Date

2023-02-21 17:20:33 UTC

HMDB ID

HMDB0031446

Secondary Accession Numbers

HMDB31446

Metabolite Identification

Common Name

p-Isopropylphenol

Description

p-Isopropylphenol, also known as 4-hydroxycumene or p-cumenol, belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. p-Isopropylphenol is a medicinal, spicy, and warm tasting compound. p-Isopropylphenol has been detected, but not quantified in, cumins (Cuminum cyminum). This could make p-isopropylphenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on p-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-4-isopropylbenzene	ChEBI
4-(1-Methylethyl)phenol	ChEBI
4-Hydroxycumene	ChEBI
p-Cumenol	ChEBI
p-Hydroxycumene	ChEBI
4-Isopropyl-phenol	ChEMBL, HMDB
4-Isopropylphenol	ChEMBL, HMDB
4-Isopropyl phenol	HMDB
Australol	HMDB
P-Cuminol	HMDB
P-Isopropyl phenol	HMDB
Para-isopropylphenol	HMDB, MeSH
p-Isopropylphenol	MeSH
4-Isopropylphenol sodium	MeSH
4-Isopropylphenol, cobalt (2+) salt	MeSH

Chemical Formula

C₉H₁₂O

Average Molecular Weight

136.191

Monoisotopic Molecular Weight

136.088815006

IUPAC Name

4-(propan-2-yl)phenol

Traditional Name

P-isopropylphenol

CAS Registry Number

99-89-8

SMILES

CC(C)C1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

YQUQWHNMBPIWGK-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-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0031446)
Cell membrane (HMDB: HMDB0031446)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031446)

Source

Endogenous

Endogenous (HMDB: HMDB0031446)

Plant

Plant (HMDB: HMDB0031446)

Exogenous

Food

Food (HMDB: HMDB0031446)

Herb and spice

Spice

Cumin (FooDB: FOOD00067)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	62.3 °C	Not Available
Boiling Point	222.00 to 223.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1102 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.90	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.81 g/L	ALOGPS
logP	2.84	ALOGPS
logP	2.91	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-5.4	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	15.8 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]+	127.976	31661259
DarkChem	[M-H]-	126.566	31661259
DeepCCS	[M+H]+	134.25	30932474
DeepCCS	[M-H]-	130.422	30932474
DeepCCS	[M-2H]-	167.848	30932474
DeepCCS	[M+Na]+	143.387	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]-	128.7	32859911
AllCCS	[M+Na-2H]-	130.4	32859911
AllCCS	[M+HCOO]-	132.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Isopropylphenol	CC(C)C1=CC=C(O)C=C1	2170.7	Standard polar	33892256
p-Isopropylphenol	CC(C)C1=CC=C(O)C=C1	1181.7	Standard non polar	33892256
p-Isopropylphenol	CC(C)C1=CC=C(O)C=C1	1218.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Isopropylphenol,1TMS,isomer #1	CC(C)C1=CC=C(O[Si](C)(C)C)C=C1	1274.4	Semi standard non polar	33892256
p-Isopropylphenol,1TBDMS,isomer #1	CC(C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1524.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - p-Isopropylphenol EI-B (Non-derivatized)	splash10-00di-3900000000-8ad6a5d0a64e2c14751b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Isopropylphenol EI-B (Non-derivatized)	splash10-00di-3900000000-8ad6a5d0a64e2c14751b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Isopropylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00du-7900000000-ac64e3ae9af14d10e2f5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Isopropylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-6900000000-4a4bf6c3109ca6b72d9e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Isopropylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 10V, Positive-QTOF	splash10-000i-0900000000-f41f82e9901d5a074e63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 20V, Positive-QTOF	splash10-000i-3900000000-9db7463bfd7eb2878614	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 40V, Positive-QTOF	splash10-0ldl-9700000000-0f7affdfac15b2c22e72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 10V, Negative-QTOF	splash10-000i-0900000000-21715a7abb65001d66cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 20V, Negative-QTOF	splash10-000i-0900000000-6f1c0faf7dd86bf552f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 40V, Negative-QTOF	splash10-00ku-5900000000-74e5fe9a940cc2275a3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 10V, Negative-QTOF	splash10-000i-0900000000-3d153ee27562ca42735c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 20V, Negative-QTOF	splash10-000i-0900000000-6f9a2d0950537b8bde81	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 40V, Negative-QTOF	splash10-00kf-9400000000-36e5abc97b5ce8260f0c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 10V, Positive-QTOF	splash10-000l-9800000000-fec57518bc07a8d008ab	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 20V, Positive-QTOF	splash10-002p-9200000000-a0f0fae3304d4a7e082b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Isopropylphenol 40V, Positive-QTOF	splash10-00or-9000000000-dd88696f3e0826e2319d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB005302

KNApSAcK ID

Not Available

Chemspider ID

7185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7465

PDB ID

Not Available

ChEBI ID

167172

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1045571

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .

Showing metabocard for p-Isopropylphenol (HMDB0031446)

MOL for HMDB0031446 (p-Isopropylphenol)

3D MOL for HMDB0031446 (p-Isopropylphenol)

3D SDF for HMDB0031446 (p-Isopropylphenol)

3D-SDF for HMDB0031446 (p-Isopropylphenol)

PDB for HMDB0031446 (p-Isopropylphenol)

3D PDB for HMDB0031446 (p-Isopropylphenol)

SMILES for HMDB0031446 (p-Isopropylphenol)

INCHI for HMDB0031446 (p-Isopropylphenol)

Structure for HMDB0031446 (p-Isopropylphenol)

3D Structure for HMDB0031446 (p-Isopropylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra