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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:30 UTC

Update Date

2023-02-21 17:22:44 UTC

HMDB ID

HMDB0032891

Secondary Accession Numbers

HMDB32891

Metabolite Identification

Common Name

1-(4-Methoxyphenyl)-2-propanone

Description

1-(4-Methoxyphenyl)-2-propanone belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 1-(4-Methoxyphenyl)-2-propanone is a sweet, anisic, and balsam tasting compound. 1-(4-Methoxyphenyl)-2-propanone is found, on average, in the highest concentration within anises (Pimpinella anisum). 1-(4-Methoxyphenyl)-2-propanone has also been detected, but not quantified in, fennels (Foeniculum vulgare) and herbs and spices. This could make 1-(4-methoxyphenyl)-2-propanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1-(4-Methoxyphenyl)-2-propanone.

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       9.177  -0.592   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.843   0.178   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.843   1.718   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.509   2.488   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.509   4.028   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.843   4.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.843   6.338   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.509   7.108   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.509   8.648   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.177   4.028   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.177   2.488   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.175   6.338   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10    3                                                       
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Methoxyphenyl)acetone	ChEMBL, HMDB
(P-Methoxyphenyl)-2-propanone	HMDB
1-(P-Anisyl)-2-propanone	HMDB
1-(P-Methoxyphenyl)-2-propanone	HMDB
4'-Methoxyphenyl-2-propanone	HMDB
4-Methoxybenzyl methyl ketone	HMDB
4-Methoxyphenoxyacetone	HMDB
4-Methoxyphenylacetone	HMDB
Anisketone	HMDB
Anisyl ketone	HMDB
Anisyl methyl ketone	HMDB
Anisylacetone?	HMDB
FEMA 2674	HMDB
P-Acetonylanisole	HMDB
P-Methoxybenzyl methyl ketone	HMDB
P-Methoxyphenylacetone	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

1-(4-methoxyphenyl)propan-2-one

Traditional Name

1-(4-methoxyphenyl)propan-2-one

CAS Registry Number

122-84-9

SMILES

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

InChI Identifier

InChI=1S/C10H12O2/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6H,7H2,1-2H3

InChI Key

WFWKNGZODAOLEO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
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

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032891)
Cytoplasm (HMDB: HMDB0032891)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032891)

Source

Exogenous

Exogenous (HMDB: HMDB0032891)

Food

Food (HMDB: HMDB0032891)

Herb and spice

Herb

Fennel (FooDB: FOOD00082)
Anise (FooDB: FOOD00137)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032891)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032891)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0032891)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	46 °C	Not Available
Boiling Point	145.00 °C. @ 25.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	1.658 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.78	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	15.82	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	3	ChemAxon
Refractivity	47.38 m³·mol⁻¹	ChemAxon
Polarizability	17.84 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]+	137.766	31661259
DarkChem	[M-H]-	137.593	31661259
DeepCCS	[M+H]+	136.565	30932474
DeepCCS	[M-H]-	132.892	30932474
DeepCCS	[M-2H]-	170.496	30932474
DeepCCS	[M+Na]+	146.035	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.4	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	137.3	32859911
AllCCS	[M+Na-2H]-	138.4	32859911
AllCCS	[M+HCOO]-	139.8	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.	5.38 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7772 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1879.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	477.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	280.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	531.8 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	570.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1174.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	434.6 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	1141.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	432.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	420.5 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	16.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(4-Methoxyphenyl)-2-propanone	COC1=CC=C(CC(C)=O)C=C1	2176.0	Standard polar	33892256
1-(4-Methoxyphenyl)-2-propanone	COC1=CC=C(CC(C)=O)C=C1	1326.6	Standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone	COC1=CC=C(CC(C)=O)C=C1	1403.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(4-Methoxyphenyl)-2-propanone,1TMS,isomer #1	COC1=CC=C(C=C(C)O[Si](C)(C)C)C=C1	1629.0	Semi standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone,1TMS,isomer #1	COC1=CC=C(C=C(C)O[Si](C)(C)C)C=C1	1593.2	Standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone,1TMS,isomer #2	C=C(CC1=CC=C(OC)C=C1)O[Si](C)(C)C	1537.5	Semi standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone,1TMS,isomer #2	C=C(CC1=CC=C(OC)C=C1)O[Si](C)(C)C	1502.8	Standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone,1TBDMS,isomer #1	COC1=CC=C(C=C(C)O[Si](C)(C)C(C)(C)C)C=C1	1879.1	Semi standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone,1TBDMS,isomer #1	COC1=CC=C(C=C(C)O[Si](C)(C)C(C)(C)C)C=C1	1823.5	Standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone,1TBDMS,isomer #2	C=C(CC1=CC=C(OC)C=C1)O[Si](C)(C)C(C)(C)C	1747.9	Semi standard non polar	33892256
1-(4-Methoxyphenyl)-2-propanone,1TBDMS,isomer #2	C=C(CC1=CC=C(OC)C=C1)O[Si](C)(C)C(C)(C)C	1712.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone EI-B (Non-derivatized)	splash10-00di-4900000000-19395666ea4a7facf293	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone EI-B (Non-derivatized)	splash10-00di-5900000000-44778fdb56d419362f0b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone EI-B (Non-derivatized)	splash10-00di-4900000000-19395666ea4a7facf293	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone EI-B (Non-derivatized)	splash10-00di-5900000000-44778fdb56d419362f0b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9800000000-2d12abd5e7d647020c7a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 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 - 1-(4-Methoxyphenyl)-2-propanone 10V, Positive-QTOF	splash10-014j-0900000000-84e15041ea5d7e701c3b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 20V, Positive-QTOF	splash10-00kb-0900000000-d805085c618e330cc26b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 40V, Positive-QTOF	splash10-014m-3900000000-01602a888dae5edd57d3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 10V, Negative-QTOF	splash10-03di-0900000000-ad761c8660e75da8bcc9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 20V, Negative-QTOF	splash10-03di-0900000000-ef34c269fe492fbdd01e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 40V, Negative-QTOF	splash10-0002-2900000000-20f8d2a119641f8e6f12	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 10V, Positive-QTOF	splash10-00xr-0900000000-ac8aefbba6143fc77a71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 20V, Positive-QTOF	splash10-00dm-4900000000-46b49a572af7a0234c21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 40V, Positive-QTOF	splash10-002f-9300000000-1295651572f4022f4108	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 10V, Negative-QTOF	splash10-03kc-4900000000-42dbfb5d4d9cace8b980	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 20V, Negative-QTOF	splash10-0596-5900000000-d9bf913c323d4d0f60ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-propanone 40V, Negative-QTOF	splash10-0006-9100000000-66e26f8f0fa944690912	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+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

FDB010873

KNApSAcK ID

C00052190

Chemspider ID

21105938

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31231

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1005711

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 1-(4-Methoxyphenyl)-2-propanone (HMDB0032891)

MOL for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

3D MOL for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

3D SDF for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

3D-SDF for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

PDB for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

3D PDB for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

SMILES for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

INCHI for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

Structure for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

3D Structure for HMDB0032891 (1-(4-Methoxyphenyl)-2-propanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra