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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:19 UTC

Update Date

2023-02-21 17:21:29 UTC

HMDB ID

HMDB0032025

Secondary Accession Numbers

HMDB32025

Metabolite Identification

Common Name

4'-Isopropylacetophenone

Description

4'-Isopropylacetophenone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4'-Isopropylacetophenone is a herbal, spicy, and woody tasting compound. Based on a literature review very few articles have been published on 4'-Isopropylacetophenone.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    1    2   10                                                  
CONECT    9    3   11   12                                                  
CONECT   10    4    5    8                                                  
CONECT   11    6    7    9                                                  
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4-Isopropylphenyl)ethanone	HMDB
1-(4-(1-Methylethyl)phenyl)-ethanone	HMDB
1-(4-(1-Methylethyl)phenyl)ethan-1-one	HMDB
1-(4-(1-Methylethyl)phenyl)ethanone	HMDB
1-(4-Isopropylphenyl)ethanone	HMDB
1-[4-(1-Methylethyl)phenyl]-ethanone	HMDB
1-[4-(1-Methylethyl)phenyl]ethanone, 9ci	HMDB
1-[4-(Propan-2-yl)phenyl]ethanone	HMDB
4'-Isopropyl-acetophenone	HMDB
4-Isopropylacetophenone	HMDB
Acetophenone, 4'-isopropyl- (8ci)	HMDB
Cuminone	HMDB
FEMA 2927	HMDB
Methyl P-cumyl ketone	HMDB
Methyl P-isopropylphenyl ketone	HMDB
P-Acetylcumene	HMDB
P-Isopropylacetophenone	HMDB
P-Isopropylacetylbenzene	HMDB

Chemical Formula

C₁₁H₁₄O

Average Molecular Weight

162.2283

Monoisotopic Molecular Weight

162.10446507

IUPAC Name

1-[4-(propan-2-yl)phenyl]ethan-1-one

Traditional Name

P-isopropylacetophenone

CAS Registry Number

645-13-6

SMILES

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

InChI Identifier

InChI=1S/C11H14O/c1-8(2)10-4-6-11(7-5-10)9(3)12/h4-8H,1-3H3

InChI Key

PDLCCNYKIIUWHA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
P-cymene
Phenylpropane
Cumene
Acetophenone
Aryl alkyl ketone
Benzoyl
Benzenoid
Monocyclic benzene moiety
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0032025)

Exogenous

Food

Food (HMDB: HMDB0032025)

Exogenous (HMDB: HMDB0032025)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0032025)

Role

Biological role

Energy source (HMDB: HMDB0032025)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032025)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032025)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	252.00 to 254.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	190.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.98	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	3.12	ALOGPS
logP	2.78	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	16.22	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.65 m³·mol⁻¹	ChemAxon
Polarizability	19.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	136.324	31661259
DarkChem	[M-H]-	135.336	31661259
DeepCCS	[M+H]+	141.689	30932474
DeepCCS	[M-H]-	138.662	30932474
DeepCCS	[M-2H]-	175.246	30932474
DeepCCS	[M+Na]+	150.654	30932474
AllCCS	[M+H]+	133.0	32859911
AllCCS	[M+H-H2O]+	128.5	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.12 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0873 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2170.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	560.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	344.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	605.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	682.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1322.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	496.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1398.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	455.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	425.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	447.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4'-Isopropylacetophenone	CC(C)C1=CC=C(C=C1)C(C)=O	1849.5	Standard polar	33892256
4'-Isopropylacetophenone	CC(C)C1=CC=C(C=C1)C(C)=O	1341.5	Standard non polar	33892256
4'-Isopropylacetophenone	CC(C)C1=CC=C(C=C1)C(C)=O	1355.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4'-Isopropylacetophenone EI-B (Non-derivatized)	splash10-0007-9600000000-4d5212924d216e344ed2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4'-Isopropylacetophenone EI-B (Non-derivatized)	splash10-0007-9600000000-4d5212924d216e344ed2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-Isopropylacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4900000000-371a43094d1b59aca250	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-Isopropylacetophenone 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 - 4'-Isopropylacetophenone 10V, Positive-QTOF	splash10-03di-0900000000-6d0ddaa9231ffecf332f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 20V, Positive-QTOF	splash10-03di-0900000000-7feabdb3db5d1abfb8b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 40V, Positive-QTOF	splash10-00kb-4900000000-8692ce63c2575167b95e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 10V, Negative-QTOF	splash10-03di-0900000000-6393e57a4daf9e75f06a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 20V, Negative-QTOF	splash10-03di-0900000000-79051021bec17cd5fe5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 40V, Negative-QTOF	splash10-014j-2900000000-48189ab8e2508b549882	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 10V, Negative-QTOF	splash10-03di-0900000000-bd5a0b9e0df7744b272c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 20V, Negative-QTOF	splash10-03di-0900000000-439b811c2b54558ef8b1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 40V, Negative-QTOF	splash10-0006-9300000000-3c97d2bc072d34ec7439	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 10V, Positive-QTOF	splash10-03di-1900000000-bd08b9ec2fbbf4c11c3c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 20V, Positive-QTOF	splash10-0006-9600000000-bfe1e20c69af74b54d95	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Isopropylacetophenone 40V, Positive-QTOF	splash10-002f-9600000000-7b01b9b7b3f16cca0d0c	2021-09-24	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB008723

KNApSAcK ID

Not Available

Chemspider ID

21105931

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12578

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1033991

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4'-Isopropylacetophenone (HMDB0032025)

MOL for HMDB0032025 (4'-Isopropylacetophenone)

3D MOL for HMDB0032025 (4'-Isopropylacetophenone)

3D SDF for HMDB0032025 (4'-Isopropylacetophenone)

3D-SDF for HMDB0032025 (4'-Isopropylacetophenone)

PDB for HMDB0032025 (4'-Isopropylacetophenone)

3D PDB for HMDB0032025 (4'-Isopropylacetophenone)

SMILES for HMDB0032025 (4'-Isopropylacetophenone)

INCHI for HMDB0032025 (4'-Isopropylacetophenone)

Structure for HMDB0032025 (4'-Isopropylacetophenone)

3D Structure for HMDB0032025 (4'-Isopropylacetophenone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra