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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:44:05 UTC

Update Date

2023-02-21 17:20:51 UTC

HMDB ID

HMDB0031566

Secondary Accession Numbers

HMDB31566

Metabolite Identification

Common Name

2-Methyl-3-phenyl-2-propenal

Description

2-Methyl-3-phenyl-2-propenal belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 2-Methyl-3-phenyl-2-propenal is a sweet, cassia, and cinnamon tasting compound. 2-Methyl-3-phenyl-2-propenal is found, on average, in the highest concentration within peppermints (Mentha X piperita). 2-Methyl-3-phenyl-2-propenal has also been detected, but not quantified in, herbs and spices. This could make 2-methyl-3-phenyl-2-propenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methyl-3-phenyl-2-propenal.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl-3-phenylacrolein	HMDB
2-Methyl-3-phenylacrylaldehyde	HMDB
2-Methylcinnamaldehyde	HMDB
3-Phenyl-2-methylacrolein	HMDB
a-Methylcinnamaldehyde, 8ci	HMDB
alpha-Methyl cinnamaldehyde	HMDB
alpha-Methylcinnamaldehyde	HMDB
alpha-Methylcinnamic aldehyde	HMDB
FEMA 2697	HMDB
Methyl cinnamic aldehyde	HMDB

Chemical Formula

C₁₀H₁₀O

Average Molecular Weight

146.1858

Monoisotopic Molecular Weight

146.073164942

IUPAC Name

(2Z)-2-methyl-3-phenylprop-2-enal

Traditional Name

(2Z)-2-methyl-3-phenylprop-2-enal

CAS Registry Number

101-39-3

SMILES

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

InChI Identifier

InChI=1S/C10H10O/c1-9(8-11)7-10-5-3-2-4-6-10/h2-8H,1H3/b9-7-

InChI Key

VLUMOWNVWOXZAU-CLFYSBASSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamaldehydes

Sub Class

Not Available

Direct Parent

Cinnamaldehydes

Alternative Parents

Substituents

Cinnamaldehyde
Benzenoid
Monocyclic benzene moiety
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

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Cellular substructure

Extracellular (HMDB: HMDB0031566)
Cytoplasm (HMDB: HMDB0031566)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031566)

Source

Endogenous

Endogenous (HMDB: HMDB0031566)

Plant

Plant (HMDB: HMDB0031566)

Exogenous

Food

Food (HMDB: HMDB0031566)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031566)

Process

Not Available

Role

Not Available

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	0.34 g/L	ALOGPS
logP	2.31	ALOGPS
logP	2.37	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.4	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	46.49 m³·mol⁻¹	ChemAxon
Polarizability	16.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	135.371	31661259
DarkChem	[M-H]-	130.962	31661259
DeepCCS	[M+H]+	136.228	30932474
DeepCCS	[M-H]-	132.546	30932474
DeepCCS	[M-2H]-	169.927	30932474
DeepCCS	[M+Na]+	145.466	30932474
AllCCS	[M+H]+	128.9	32859911
AllCCS	[M+H-H2O]+	124.2	32859911
AllCCS	[M+NH4]+	133.2	32859911
AllCCS	[M+Na]+	134.4	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	132.3	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.	6.56 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7493 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2098.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	541.8 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	344.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	629.4 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	706.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	149.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1274.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	518.2 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	1317.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	490.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	449.5 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	28.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-3-phenyl-2-propenal	C\C(C=O)=C\C1=CC=CC=C1	1935.6	Standard polar	33892256
2-Methyl-3-phenyl-2-propenal	C\C(C=O)=C\C1=CC=CC=C1	1260.2	Standard non polar	33892256
2-Methyl-3-phenyl-2-propenal	C\C(C=O)=C\C1=CC=CC=C1	1270.4	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 - 2-Methyl-3-phenyl-2-propenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kg-6900000000-a06eb85c5a48ce4c78b5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-3-phenyl-2-propenal 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 - 2-Methyl-3-phenyl-2-propenal 10V, Positive-QTOF	splash10-0002-1900000000-89ab9e019921255893f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 20V, Positive-QTOF	splash10-00kb-8900000000-b4fddb38764c2c9112fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 40V, Positive-QTOF	splash10-0gbl-9200000000-262050491995fee32332	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 10V, Negative-QTOF	splash10-0002-0900000000-221c71bf5191ae84a50e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 20V, Negative-QTOF	splash10-014j-0900000000-4be4c949046e9bb00c50	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 40V, Negative-QTOF	splash10-014i-3900000000-8c03758b70ae4bf0c7e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 10V, Negative-QTOF	splash10-0002-2900000000-1e835d97d6d3fd0993c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 20V, Negative-QTOF	splash10-014i-1900000000-1a7698375179f8fdf4f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 40V, Negative-QTOF	splash10-00mo-9600000000-e61ade7c9bf9d4acdf5f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 10V, Positive-QTOF	splash10-0007-7900000000-00e6c8e4d96624db33c4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 20V, Positive-QTOF	splash10-00kf-9400000000-5c48c4453f7f8a9ccd14	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-phenyl-2-propenal 40V, Positive-QTOF	splash10-00kf-9300000000-79020505f67f2f9a1d28	2021-09-23	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

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

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

FDB008181

KNApSAcK ID

C00056330

Chemspider ID

4510994

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5354896

PDB ID

Not Available

ChEBI ID

89992

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 2-Methyl-3-phenyl-2-propenal (HMDB0031566)

MOL for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

3D MOL for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

3D SDF for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

3D-SDF for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

PDB for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

3D PDB for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

SMILES for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

INCHI for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

Structure for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

3D Structure for HMDB0031566 (2-Methyl-3-phenyl-2-propenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra