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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:31:24 UTC

Update Date

2023-02-21 17:25:46 UTC

HMDB ID

HMDB0037281

Secondary Accession Numbers

HMDB37281

Metabolite Identification

Common Name

4-Methyl-2-phenyl-2-pentenal

Description

4-Methyl-2-phenyl-2-pentenal belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 4-Methyl-2-phenyl-2-pentenal is a sweet, cocoa, and nutty tasting compound. 4-Methyl-2-phenyl-2-pentenal has been detected, but not quantified in, several different foods, such as potatos (Solanum tuberosum), green tea, teas (Camellia sinensis), nuts, and black tea. This could make 4-methyl-2-phenyl-2-pentenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Methyl-2-phenyl-2-pentenal.

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       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   6.160   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  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   10   12                                                       
CONECT    9   12   13                                                       
CONECT   10    1    2    8                                                  
CONECT   11    6    7   12                                                  
CONECT   12    8    9   11                                                  
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0037281
HETATM    1  C1  UNL     1      -2.998  -1.045   0.638  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.371   0.239   0.099  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.042   0.626  -1.217  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.960  -0.072  -0.144  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.029   0.588   0.426  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.203   1.681   1.339  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.705   2.309   1.893  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.406   0.138   0.116  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.526   0.824   0.525  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.818   0.360   0.249  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.041  -0.801  -0.443  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.928  -1.489  -0.853  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.634  -1.030  -0.580  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.751  -0.815   1.408  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.230  -1.687   1.119  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.419  -1.581  -0.236  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.591   1.019   0.799  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.641  -0.026  -2.027  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.848   1.697  -1.380  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.130   0.503  -1.112  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.752  -0.867  -0.828  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.224   1.966   1.550  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.456   1.747   1.058  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.678   0.947   0.599  1.00  0.00           H  
HETATM   25  H12 UNL     1       5.040  -1.166  -0.659  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.080  -2.419  -1.407  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.820  -1.645  -0.934  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   19   20
CONECT    4    5    5   21
CONECT    5    6    8
CONECT    6    7    7   22
CONECT    8    9    9   13
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2Z)-4-Methyl-2-phenyl-2-pentenal	HMDB
4-Methyl-2-phenyl-2-penteral	HMDB
a-(2-Methylpropylidene)benzeneacetaldehyde, 9ci	HMDB
alpha-(2-Methylpropylidene)-benzeneacetaldehyde	HMDB
alpha-(2-Methylpropylidene)benzeneacetaldehyde	HMDB
alpha-Isobutylidenebenzeneacetaldehyde	HMDB
FEMA 3200	HMDB

Chemical Formula

C₁₂H₁₄O

Average Molecular Weight

174.239

Monoisotopic Molecular Weight

174.10446507

IUPAC Name

(2Z)-4-methyl-2-phenylpent-2-enal

Traditional Name

(2Z)-4-methyl-2-phenylpent-2-enal

CAS Registry Number

26643-91-4

SMILES

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

InChI Identifier

InChI=1S/C12H14O/c1-10(2)8-12(9-13)11-6-4-3-5-7-11/h3-10H,1-2H3/b12-8+

InChI Key

ULRYRAHIBWLZKC-XYOKQWHBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetaldehydes

Direct Parent

Phenylacetaldehydes

Alternative Parents

Substituents

Phenylacetaldehyde
Styrene
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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

Membrane (HMDB: HMDB0037281)
Cell membrane (HMDB: HMDB0037281)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037281)

Source

Exogenous

Food

Food (HMDB: HMDB0037281)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Nut

Nuts (FooDB: FOOD00869)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Endogenous

Plant

Plant (HMDB: HMDB0037281)

Animal

Animal (HMDB: HMDB0037281)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037281)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	82.00 to 87.00 °C. @ 0.70 mm Hg	The Good Scents Company Information System
Water Solubility	93.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.554 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	3.15	ALOGPS
logP	3.16	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-4.5	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	3	ChemAxon
Refractivity	55.64 m³·mol⁻¹	ChemAxon
Polarizability	20.25 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]+	143.015	31661259
DarkChem	[M-H]-	142.338	31661259
DeepCCS	[M+H]+	143.223	30932474
DeepCCS	[M-H]-	140.865	30932474
DeepCCS	[M-2H]-	175.76	30932474
DeepCCS	[M+Na]+	150.73	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	140.8	32859911
AllCCS	[M+Na]+	141.9	32859911
AllCCS	[M-H]-	140.2	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	142.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-2-phenyl-2-pentenal	CC(C)\C=C(/C=O)C1=CC=CC=C1	1950.5	Standard polar	33892256
4-Methyl-2-phenyl-2-pentenal	CC(C)\C=C(/C=O)C1=CC=CC=C1	1352.2	Standard non polar	33892256
4-Methyl-2-phenyl-2-pentenal	CC(C)\C=C(/C=O)C1=CC=CC=C1	1390.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-2-phenyl-2-pentenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6t-1900000000-2a202d976af8d36196d4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 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-Methyl-2-phenyl-2-pentenal 10V, Positive-QTOF	splash10-004i-0900000000-e67fd33516eb9ca01b3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 20V, Positive-QTOF	splash10-00or-3900000000-030b9f91eb9a6a58a366	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 40V, Positive-QTOF	splash10-0aor-9500000000-e3e2f9210935de9c34b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 10V, Negative-QTOF	splash10-00di-0900000000-05fc4e13726153e31918	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 20V, Negative-QTOF	splash10-00di-3900000000-580fa55572784b9bda8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 40V, Negative-QTOF	splash10-016r-9600000000-8a2dac4fb7f5bbd556b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 10V, Positive-QTOF	splash10-002b-0900000000-4b1f7bf10e0813084b00	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 20V, Positive-QTOF	splash10-0fry-3900000000-dc5ebfbbb2fee1a7d8c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 40V, Positive-QTOF	splash10-0udl-5900000000-d83e96b6c7be7ea32c59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 10V, Negative-QTOF	splash10-00di-0900000000-abdc9670be2cfbec1485	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 20V, Negative-QTOF	splash10-0002-0900000000-a8ef866623875518f134	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-phenyl-2-pentenal 40V, Negative-QTOF	splash10-0fb9-1900000000-d9d03e277bba975fb180	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

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

FDB016300

KNApSAcK ID

Not Available

Chemspider ID

4516189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363896

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1022441

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-Methyl-2-phenyl-2-pentenal (HMDB0037281)

MOL for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

3D MOL for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

3D SDF for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

3D-SDF for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

PDB for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

3D PDB for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

SMILES for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

INCHI for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

Structure for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

3D Structure for HMDB0037281 (4-Methyl-2-phenyl-2-pentenal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra