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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:17:52 UTC

Update Date

2023-02-21 17:23:26 UTC

HMDB ID

HMDB0033562

Secondary Accession Numbers

HMDB33562

Metabolite Identification

Common Name

3-Methyl-2-phenylbutanal

Description

3-Methyl-2-phenylbutanal 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. 3-Methyl-2-phenylbutanal is a bitter, fruity, and green tasting compound. Based on a literature review very few articles have been published on 3-Methyl-2-phenylbutanal.

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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8   11   12                                                       
CONECT    9    1    2   11                                                  
CONECT   10    6    7   11                                                  
CONECT   11    8    9   10                                                  
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
3-Methyl-2-phenyl-butraldehyde	HMDB
3-Methyl-2-phenylbutyraldehyde	HMDB
a-(1-Methylethyl)benzeneacetaldehyde, 9ci	HMDB
alpha-(1-Methylethyl)-benzeneacetaldehyde	HMDB
alpha-(1-Methylethyl)benzeneacetaldehyde	HMDB
alpha-Isopropylphenylacetaldehyde	HMDB
alpha-Phenylisopentanal	HMDB
alpha-Phenylisovaleraldehyde	HMDB
FEMA 2738	HMDB

Chemical Formula

C₁₁H₁₄O

Average Molecular Weight

162.2283

Monoisotopic Molecular Weight

162.10446507

IUPAC Name

3-methyl-2-phenylbutanal

Traditional Name

3-methyl-2-phenylbutanal

CAS Registry Number

2439-44-3

SMILES

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

InChI Identifier

InChI=1S/C11H14O/c1-9(2)11(8-12)10-6-4-3-5-7-10/h3-9,11H,1-2H3

InChI Key

UKEXEDXJYSMZGZ-UHFFFAOYSA-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

Phenylpropane
Phenylacetaldehyde
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

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033562)
Cell membrane (HMDB: HMDB0033562)

Source

Exogenous

Exogenous (HMDB: HMDB0033562)

Food

Food (HMDB: HMDB0033562)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033562)

Biological role

Nutrient (HMDB: HMDB0033562)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	238.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	237.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.005 (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	2.9	ALOGPS
logP	2.73	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	-7.1	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	50.16 m³·mol⁻¹	ChemAxon
Polarizability	18.61 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]+	136.899	31661259
DarkChem	[M-H]-	132.471	31661259
DeepCCS	[M+H]+	136.581	30932474
DeepCCS	[M-H]-	133.652	30932474
DeepCCS	[M-2H]-	170.343	30932474
DeepCCS	[M+Na]+	145.882	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	137.8	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	139.5	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.	7.11 minutes	32390414
Predicted by Siyang on May 30, 2022	16.7334 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.69 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2136.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	602.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	229.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	377.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	722.2 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	775.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1411.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	550.0 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	1479.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	457.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	459.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	471.3 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	15.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-phenylbutanal	CC(C)C(C=O)C1=CC=CC=C1	1748.0	Standard polar	33892256
3-Methyl-2-phenylbutanal	CC(C)C(C=O)C1=CC=CC=C1	1240.0	Standard non polar	33892256
3-Methyl-2-phenylbutanal	CC(C)C(C=O)C1=CC=CC=C1	1254.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-phenylbutanal,1TMS,isomer #1	CC(C)C(=CO[Si](C)(C)C)C1=CC=CC=C1	1461.2	Semi standard non polar	33892256
3-Methyl-2-phenylbutanal,1TMS,isomer #1	CC(C)C(=CO[Si](C)(C)C)C1=CC=CC=C1	1424.7	Standard non polar	33892256
3-Methyl-2-phenylbutanal,1TBDMS,isomer #1	CC(C)C(=CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1684.3	Semi standard non polar	33892256
3-Methyl-2-phenylbutanal,1TBDMS,isomer #1	CC(C)C(=CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1637.2	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-2-phenylbutanal GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-6900000000-f60aa504d57ee0bdef3c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-phenylbutanal 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-2-phenylbutanal 10V, Positive-QTOF	splash10-03di-0900000000-d210be5f4740213c1dd0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 20V, Positive-QTOF	splash10-03k9-2900000000-574519aed138132a48a7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 40V, Positive-QTOF	splash10-00mp-9800000000-d5c751a1390c327258b7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 10V, Negative-QTOF	splash10-03di-0900000000-922ceae1d718a317bfd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 20V, Negative-QTOF	splash10-03di-1900000000-2bef402575406fd4737d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 40V, Negative-QTOF	splash10-00o3-9400000000-3487bd4c9d14032b077d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 10V, Positive-QTOF	splash10-0006-5900000000-653fb6d3cb14372c536a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 20V, Positive-QTOF	splash10-0006-9500000000-8b3d0f02ccaa495e35f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 40V, Positive-QTOF	splash10-0006-9500000000-d3849f64b2fc9465e429	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 10V, Negative-QTOF	splash10-01q9-0900000000-58c5160654621f032cdd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 20V, Negative-QTOF	splash10-001i-2900000000-d0c10b113510dc7ea46b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-phenylbutanal 40V, Negative-QTOF	splash10-00or-9500000000-9d160b43f23992949eb1	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

FDB011631

KNApSAcK ID

Not Available

Chemspider ID

15962892

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12255414

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1032941

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-2-phenylbutanal (HMDB0033562)

MOL for HMDB0033562 (3-Methyl-2-phenylbutanal)

3D MOL for HMDB0033562 (3-Methyl-2-phenylbutanal)

3D SDF for HMDB0033562 (3-Methyl-2-phenylbutanal)

3D-SDF for HMDB0033562 (3-Methyl-2-phenylbutanal)

PDB for HMDB0033562 (3-Methyl-2-phenylbutanal)

3D PDB for HMDB0033562 (3-Methyl-2-phenylbutanal)

SMILES for HMDB0033562 (3-Methyl-2-phenylbutanal)

INCHI for HMDB0033562 (3-Methyl-2-phenylbutanal)

Structure for HMDB0033562 (3-Methyl-2-phenylbutanal)

3D Structure for HMDB0033562 (3-Methyl-2-phenylbutanal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra