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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:20:37 UTC

Update Date

2023-02-21 17:23:28 UTC

HMDB ID

HMDB0033597

Secondary Accession Numbers

HMDB33597

Metabolite Identification

Common Name

4-(4-Methoxyphenyl)-2-butanone

Description

4-(4-Methoxyphenyl)-2-butanone belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 4-(4-Methoxyphenyl)-2-butanone is a sweet, absolute, and cassie tasting compound. 4-(4-Methoxyphenyl)-2-butanone has been detected, but not quantified in, herbs and spices. This could make 4-(4-methoxyphenyl)-2-butanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-(4-Methoxyphenyl)-2-butanone.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.970  -8.305   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.304  -9.075   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.304 -10.615   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.970 -11.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.636 -10.615   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.636  -9.075   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.637  -8.305   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.971  -9.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.303 -11.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.031 -10.615   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.365 -11.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.698 -10.615   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.365 -12.925   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0033597
HETATM    1  C1  UNL     1      -4.864   0.928   0.184  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.994   0.450  -0.816  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.692   0.065  -0.544  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.160   0.124   0.728  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.849  -0.268   0.980  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.069  -0.723  -0.061  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.332  -1.142   0.209  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.230   0.091   0.039  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.647  -0.284   0.302  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.711   0.726   0.204  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.925  -1.434   0.599  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.578  -0.793  -1.347  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.899  -0.393  -1.576  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.347   1.650   0.869  1.00  0.00           H  
HETATM   15  H2  UNL     1      -5.321   0.081   0.733  1.00  0.00           H  
HETATM   16  H3  UNL     1      -5.706   1.469  -0.338  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.800   0.486   1.523  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.484  -0.199   2.006  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.677  -1.895  -0.549  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.473  -1.603   1.189  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.882   0.904   0.703  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.184   0.421  -1.018  1.00  0.00           H  
HETATM   23  H10 UNL     1       5.031   0.993   1.243  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.323   1.623  -0.292  1.00  0.00           H  
HETATM   25  H12 UNL     1       5.617   0.318  -0.331  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.041  -1.152  -2.163  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.312  -0.441  -2.573  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7   12
CONECT    7    8   19   20
CONECT    8    9   21   22
CONECT    9   10   11   11
CONECT   10   23   24   25
CONECT   12   13   13   26
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Methoxyphenyl)-3-butanone	HMDB
1-(P-Methoxyphenyl)-3-butanone	HMDB
2-Butanone, 4-(P-methoxyphenyl)- (6ci,7ci,8ci)	HMDB
4-(4-Methoxyphenyl)-butan-2-one	HMDB
4-(P-Methoxyphenyl)-2-butanone	HMDB
4-Methoxybenzylacetone	HMDB
Anisylacetone	HMDB
FEMA 2672	HMDB
P-Anisylacetone	HMDB
P-Methoxybenzylacetone	HMDB
P-Methoxyphenylbutanone	HMDB
Rasberry ketone methyl ether	HMDB
Raspberry ketone methyl ether	HMDB

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

4-(4-methoxyphenyl)butan-2-one

Traditional Name

4-(4-methoxyphenyl)butan-2-one

CAS Registry Number

104-20-1

SMILES

COC1=CC=C(CCC(C)=O)C=C1

InChI Identifier

InChI=1S/C11H14O2/c1-9(12)3-4-10-5-7-11(13-2)8-6-10/h5-8H,3-4H2,1-2H3

InChI Key

PCBSXBYCASFXTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Methoxybenzene
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033597)
Cytoplasm (HMDB: HMDB0033597)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033597)

Source

Exogenous

Exogenous (HMDB: HMDB0033597)

Food

Food (HMDB: HMDB0033597)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033597)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033597)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	9 - 10 °C	Not Available
Boiling Point	152.00 to 153.00 °C. @ 15.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	1.852 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	1.96	ALOGPS
logP	2.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.98 m³·mol⁻¹	ChemAxon
Polarizability	20.12 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]+	142.678	31661259
DarkChem	[M-H]-	141.277	31661259
DeepCCS	[M+H]+	142.988	30932474
DeepCCS	[M-H]-	139.161	30932474
DeepCCS	[M-2H]-	176.828	30932474
DeepCCS	[M+Na]+	152.367	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	143.5	32859911
AllCCS	[M+Na]+	144.6	32859911
AllCCS	[M-H]-	142.7	32859911
AllCCS	[M+Na-2H]-	143.6	32859911
AllCCS	[M+HCOO]-	144.8	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.	6.01 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2106 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2046.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	475.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	277.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	559.1 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	590.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1249.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	455.4 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	1219.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	405.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	386.1 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	11.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(4-Methoxyphenyl)-2-butanone	COC1=CC=C(CCC(C)=O)C=C1	2284.9	Standard polar	33892256
4-(4-Methoxyphenyl)-2-butanone	COC1=CC=C(CCC(C)=O)C=C1	1426.3	Standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone	COC1=CC=C(CCC(C)=O)C=C1	1501.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(4-Methoxyphenyl)-2-butanone,1TMS,isomer #1	COC1=CC=C(CC=C(C)O[Si](C)(C)C)C=C1	1687.6	Semi standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone,1TMS,isomer #1	COC1=CC=C(CC=C(C)O[Si](C)(C)C)C=C1	1629.8	Standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone,1TMS,isomer #2	C=C(CCC1=CC=C(OC)C=C1)O[Si](C)(C)C	1640.6	Semi standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone,1TMS,isomer #2	C=C(CCC1=CC=C(OC)C=C1)O[Si](C)(C)C	1606.8	Standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone,1TBDMS,isomer #1	COC1=CC=C(CC=C(C)O[Si](C)(C)C(C)(C)C)C=C1	1930.0	Semi standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone,1TBDMS,isomer #1	COC1=CC=C(CC=C(C)O[Si](C)(C)C(C)(C)C)C=C1	1874.6	Standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=CC=C(OC)C=C1)O[Si](C)(C)C(C)(C)C	1884.4	Semi standard non polar	33892256
4-(4-Methoxyphenyl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=CC=C(OC)C=C1)O[Si](C)(C)C(C)(C)C	1821.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone EI-B (Non-derivatized)	splash10-00di-5900000000-47c1f7655edcdfde74c6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone EI-B (Non-derivatized)	splash10-00di-5900000000-47c1f7655edcdfde74c6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6900000000-0e464820da0a2ad34901	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 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-(4-Methoxyphenyl)-2-butanone 10V, Positive-QTOF	splash10-01t9-0900000000-fb91b7380eab0d1d46a2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 20V, Positive-QTOF	splash10-03fr-1900000000-53bdf5e2726d42023c00	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 40V, Positive-QTOF	splash10-0udi-6900000000-2f1b90d54a890adbde3b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 10V, Negative-QTOF	splash10-004i-0900000000-34a11443c7a4f32f0c7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 20V, Negative-QTOF	splash10-004i-0900000000-a92a2296d3fc1aa5cfa6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 40V, Negative-QTOF	splash10-08fu-2900000000-371a092e4c9f26dbbfe9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 10V, Negative-QTOF	splash10-0a6r-9500000000-a3cdd66b758aa32c8a75	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 20V, Negative-QTOF	splash10-0a4i-9400000000-21f8cbe8cf90bad50c86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 40V, Negative-QTOF	splash10-0ar3-8900000000-0a3dcd3ac26dba1e0142	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 10V, Positive-QTOF	splash10-024i-0900000000-faef2f5115e472c8ef2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 20V, Positive-QTOF	splash10-0229-3900000000-3f15e84d9f9733e6c2a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4-Methoxyphenyl)-2-butanone 40V, Positive-QTOF	splash10-004i-9800000000-32e1d913fad7e645cd5e	2021-09-22	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

Cytoplasm
Extracellular

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

FDB011682

KNApSAcK ID

C00054097

Chemspider ID

54968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61007

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1021652

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-(4-Methoxyphenyl)-2-butanone (HMDB0033597)

MOL for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

3D MOL for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

3D SDF for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

3D-SDF for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

PDB for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

3D PDB for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

SMILES for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

INCHI for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

Structure for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

3D Structure for HMDB0033597 (4-(4-Methoxyphenyl)-2-butanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra