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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:18:15 UTC

Update Date

2023-02-21 17:28:53 UTC

HMDB ID

HMDB0041612

Secondary Accession Numbers

HMDB41612

Metabolite Identification

Common Name

Phenyl butyrate

Description

Phenyl butyrate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Phenyl butyrate is a sweet and floral tasting compound. Based on a literature review very few articles have been published on Phenyl butyrate.

Structure

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

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    2   10                                                       
CONECT    7    4    9                                                       
CONECT    8    5    9                                                       
CONECT    9    7    8   12                                                  
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Phenyl butyric acid	Generator
Butanoic acid, 9ci	HMDB
PH Ester	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.204

Monoisotopic Molecular Weight

164.083729626

IUPAC Name

phenyl butanoate

Traditional Name

α-ethylphenylacetate

CAS Registry Number

4346-18-3

SMILES

CCCC(=O)OC1=CC=CC=C1

InChI Identifier

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

InChI Key

IGVPBCZDHMIOJH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Fatty acid ester
Fatty acyl
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	225.00 to 226.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	416.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.672 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.73	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	46.42 m³·mol⁻¹	ChemAxon
Polarizability	18.2 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]+	136.699	31661259
DarkChem	[M-H]-	135.569	31661259
DeepCCS	[M+H]+	134.484	30932474
DeepCCS	[M-H]-	130.656	30932474
DeepCCS	[M-2H]-	168.249	30932474
DeepCCS	[M+Na]+	143.787	30932474
AllCCS	[M+H]+	136.6	32859911
AllCCS	[M+H-H2O]+	132.4	32859911
AllCCS	[M+NH4]+	140.6	32859911
AllCCS	[M+Na]+	141.8	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	140.1	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.	6.74 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5441 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2104.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	548.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	344.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	642.2 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	667.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1335.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	478.7 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	1320.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	441.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	485.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	466.5 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	42.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenyl butyrate	CCCC(=O)OC1=CC=CC=C1	1843.6	Standard polar	33892256
Phenyl butyrate	CCCC(=O)OC1=CC=CC=C1	1253.6	Standard non polar	33892256
Phenyl butyrate	CCCC(=O)OC1=CC=CC=C1	1288.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenyl butyrate EI-B (Non-derivatized)	splash10-0006-9000000000-1fad10cfe43dc1f09a35	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenyl butyrate EI-B (Non-derivatized)	splash10-0006-9000000000-1fad10cfe43dc1f09a35	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenyl butyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-4f8c7e1c0dcbddfffeec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenyl butyrate 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 - Phenyl butyrate 10V, Positive-QTOF	splash10-014i-7900000000-78aec81ddbe5f64c887c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 20V, Positive-QTOF	splash10-006t-9100000000-901be2b861bbe95533c0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 40V, Positive-QTOF	splash10-0udm-9000000000-d483adeaf1f40050e614	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 10V, Negative-QTOF	splash10-03di-5900000000-86ca90ba156ce398427b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 20V, Negative-QTOF	splash10-0006-9300000000-e5f9cc696d683274bb70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 40V, Negative-QTOF	splash10-0006-9000000000-966cde9d94bdea7cc72b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 10V, Negative-QTOF	splash10-0006-9300000000-83deda1a3ec74ef649f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 20V, Negative-QTOF	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 40V, Negative-QTOF	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 10V, Positive-QTOF	splash10-00kb-9600000000-ea36b84a11464746317a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 20V, Positive-QTOF	splash10-0002-9100000000-9f5622ae8bcc05bccc54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyl butyrate 40V, Positive-QTOF	splash10-002f-9000000000-42edafbfc8458177cf49	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

FDB021767

KNApSAcK ID

Not Available

Chemspider ID

19172

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20354

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1460621

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 Phenyl butyrate (HMDB0041612)

MOL for HMDB0041612 (Phenyl butyrate)

3D MOL for HMDB0041612 (Phenyl butyrate)

3D SDF for HMDB0041612 (Phenyl butyrate)

3D-SDF for HMDB0041612 (Phenyl butyrate)

PDB for HMDB0041612 (Phenyl butyrate)

3D PDB for HMDB0041612 (Phenyl butyrate)

SMILES for HMDB0041612 (Phenyl butyrate)

INCHI for HMDB0041612 (Phenyl butyrate)

Structure for HMDB0041612 (Phenyl butyrate)

3D Structure for HMDB0041612 (Phenyl butyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra