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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:05 UTC

Update Date

2023-02-21 17:20:51 UTC

HMDB ID

HMDB0031567

Secondary Accession Numbers

HMDB31567

Metabolite Identification

Common Name

3-Methyl-4-phenyl-3-buten-2-one

Description

3-Methyl-4-phenyl-3-buten-2-one belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 3-Methyl-4-phenyl-3-buten-2-one is a berry, camphor, and fruity tasting compound. Based on a literature review very few articles have been published on 3-Methyl-4-phenyl-3-buten-2-one.

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       0.075  -2.846   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.307  -3.614   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.692  -2.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.692  -1.307   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.307  -0.537   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.075  -1.307   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.307  -0.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.307   1.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.075   2.076   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.537   3.614   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.692   1.769   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.461   1.769   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9                                                            
CONECT   11    8                                                            
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
3-Benzylidene-2-butanone	HMDB
FEMA 2734	HMDB

Chemical Formula

C₁₁H₁₂O

Average Molecular Weight

160.2124

Monoisotopic Molecular Weight

160.088815006

IUPAC Name

(3Z)-3-methyl-4-phenylbut-3-en-2-one

Traditional Name

(3Z)-3-methyl-4-phenylbut-3-en-2-one

CAS Registry Number

1901-26-4

SMILES

CC(=O)C(\C)=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H12O/c1-9(10(2)12)8-11-6-4-3-5-7-11/h3-8H,1-2H3/b9-8-

InChI Key

BQJFBHBDOAIIGS-HJWRWDBZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Alpha-branched alpha,beta-unsaturated-ketone
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0031567)
Cell membrane (HMDB: HMDB0031567)

Source

Exogenous

Food

Food (HMDB: HMDB0031567)

Exogenous (HMDB: HMDB0031567)

Endogenous

Endogenous (HMDB: HMDB0031567)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031567)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.86	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	19.56	ChemAxon
pKa (Strongest Basic)	-4.7	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	50.97 m³·mol⁻¹	ChemAxon
Polarizability	17.92 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
DeepCCS	[M+H]+	136.93	30932474
DeepCCS	[M-H]-	134.389	30932474
DeepCCS	[M-2H]-	170.005	30932474
DeepCCS	[M+Na]+	145.087	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	134.9	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	137.1	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.	7.38 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6447 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2365.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	571.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	213.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	351.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	648.9 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	695.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1375.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	541.1 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	1395.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	457.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	446.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	450.5 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	16.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-4-phenyl-3-buten-2-one	CC(=O)C(\C)=C/C1=CC=CC=C1	2016.6	Standard polar	33892256
3-Methyl-4-phenyl-3-buten-2-one	CC(=O)C(\C)=C/C1=CC=CC=C1	1342.5	Standard non polar	33892256
3-Methyl-4-phenyl-3-buten-2-one	CC(=O)C(\C)=C/C1=CC=CC=C1	1395.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-4-phenyl-3-buten-2-one,1TMS,isomer #1	C=C(O[Si](C)(C)C)/C(C)=C\C1=CC=CC=C1	1497.4	Semi standard non polar	33892256
3-Methyl-4-phenyl-3-buten-2-one,1TMS,isomer #1	C=C(O[Si](C)(C)C)/C(C)=C\C1=CC=CC=C1	1488.3	Standard non polar	33892256
3-Methyl-4-phenyl-3-buten-2-one,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C\C1=CC=CC=C1	1756.0	Semi standard non polar	33892256
3-Methyl-4-phenyl-3-buten-2-one,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C\C1=CC=CC=C1	1705.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-4900000000-72d080e0d609e40d9b6d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 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 - 3-Methyl-4-phenyl-3-buten-2-one 10V, Positive-QTOF	splash10-03di-2900000000-fb2c649951e83652e217	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 20V, Positive-QTOF	splash10-03xu-4900000000-b4543686369bb9898d37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 40V, Positive-QTOF	splash10-0uxu-9300000000-965fd255f7721b7cf853	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 10V, Negative-QTOF	splash10-0a4i-0900000000-add03102c04a9d5fbbcb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 20V, Negative-QTOF	splash10-0aor-1900000000-64e31d0f4a90289919bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 40V, Negative-QTOF	splash10-014l-6900000000-d5bf7af438778b41b81c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 10V, Negative-QTOF	splash10-0a4i-0900000000-670eabbc1acdf7ee7567	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 20V, Negative-QTOF	splash10-066u-3900000000-4e0fef32d1b67a570895	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 40V, Negative-QTOF	splash10-00kf-9600000000-42b126296e3c9f01bb29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 10V, Positive-QTOF	splash10-03dl-5900000000-dadf8212a9fe0d2bfc20	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 20V, Positive-QTOF	splash10-0006-9400000000-58e294c0c880476b23d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-phenyl-3-buten-2-one 40V, Positive-QTOF	splash10-0006-9300000000-5296cdafa05c5d8e7bb9	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

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

FDB008182

KNApSAcK ID

Not Available

Chemspider ID

4511767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5355902

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 3-Methyl-4-phenyl-3-buten-2-one (HMDB0031567)

MOL for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

3D MOL for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

3D SDF for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

3D-SDF for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

PDB for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

3D PDB for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

SMILES for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

INCHI for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

Structure for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

3D Structure for HMDB0031567 (3-Methyl-4-phenyl-3-buten-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra