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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:37 UTC

Update Date

2023-02-21 17:21:36 UTC

HMDB ID

HMDB0032075

Secondary Accession Numbers

HMDB32075

Metabolite Identification

Common Name

p-Tolyl acetate

Description

p-Tolyl acetate, also known as p-tolyacetic acid, 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. p-Tolyl acetate is an animal, narcissus, and phenolic tasting compound. p-Tolyl acetate has been detected, but not quantified in, herbs and spices. This could make p-tolyl acetate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on p-Tolyl acetate.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
p-Cresyl acetate	Kegg
p-Tolyacetate	Kegg
p-Cresyl acetic acid	Generator
p-Tolyacetic acid	Generator
p-Tolyl acetic acid	Generator
(4-Methylphenyl)acetic acid	HMDB
(P-Tolyl)-acetic acid	HMDB
(P-Tolyl)acetic acid	HMDB
4-Acetoxytoluene	HMDB
4-Methyl-benzeneacetic acid	HMDB
4-Methylbenzeneacetic acid	HMDB
4-Methylbenzoic acid methyl ester	HMDB
4-Methylphenyl acetate	HMDB
4-Tolyl acetate	HMDB
Acetic acid P-cresyl ester	HMDB
Acetic acid, 4-methylphenyl ester	HMDB
Acetic acid, P-tolyl ester	HMDB
Benzeneacetic acid, 4-methyl- (9ci)	HMDB
Cresyl acetate	HMDB, MeSH
FEMA 3073	HMDB
Narceol	HMDB
P-Acetoxytoluene	HMDB
P-Cresol acetate	HMDB
P-Cresyl acetate FCC	HMDB
P-Cresylic acetate	HMDB
P-Methylphenyl acetate	HMDB
P-Methylphenylacetic acid	HMDB
P-Tolyl ethanoate	HMDB
P-Tolylacetic acid	HMDB
Paracresyl acetate	HMDB
Tolylacetate	HMDB
4-Cresyl acetate	MeSH, HMDB
Para-cresyl acetate	MeSH, HMDB
Tolylacetic acid	Generator

Chemical Formula

C₉H₁₀O₂

Average Molecular Weight

150.1745

Monoisotopic Molecular Weight

150.068079564

IUPAC Name

4-methylphenyl acetate

Traditional Name

humibid

CAS Registry Number

140-39-6

SMILES

CC(=O)OC1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C9H10O2/c1-7-3-5-9(6-4-7)11-8(2)10/h3-6H,1-2H3

InChI Key

CDJJKTLOZJAGIZ-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
Toluene
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

phenols (CHEBI:9627 )
benzoate ester (CHEBI:9627 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032075)
Cytoplasm (HMDB: HMDB0032075)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032075)

Source

Endogenous

Endogenous (HMDB: HMDB0032075)

Plant

Plant (HMDB: HMDB0032075)

Exogenous

Food

Food (HMDB: HMDB0032075)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0032075)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032075)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	208.00 to 212.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1195 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.11	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	1.96	ALOGPS
logP	2.09	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-7.1	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	2	ChemAxon
Refractivity	42.23 m³·mol⁻¹	ChemAxon
Polarizability	16.32 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]+	134.499	31661259
DarkChem	[M-H]-	131.785	31661259
DeepCCS	[M+H]+	134.417	30932474
DeepCCS	[M-H]-	131.129	30932474
DeepCCS	[M-2H]-	168.193	30932474
DeepCCS	[M+Na]+	143.731	30932474
AllCCS	[M+H]+	130.2	32859911
AllCCS	[M+H-H2O]+	125.7	32859911
AllCCS	[M+NH4]+	134.5	32859911
AllCCS	[M+Na]+	135.7	32859911
AllCCS	[M-H]-	131.3	32859911
AllCCS	[M+Na-2H]-	132.7	32859911
AllCCS	[M+HCOO]-	134.2	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.	5.3 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5367 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1796.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	522.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	334.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	593.5 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	595.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	133.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1227.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	460.1 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	1351.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	399.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	454.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	339.3 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	65.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Tolyl acetate	CC(=O)OC1=CC=C(C)C=C1	1762.1	Standard polar	33892256
p-Tolyl acetate	CC(=O)OC1=CC=C(C)C=C1	1152.5	Standard non polar	33892256
p-Tolyl acetate	CC(=O)OC1=CC=C(C)C=C1	1179.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-4900000000-1e63cc956c8aa5d2b50e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-5900000000-7e9142ca5636b3537762	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-4900000000-84f9b68467e23b1b2be6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-1900000000-20ee4619821736a9315b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-4900000000-1e63cc956c8aa5d2b50e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-5900000000-7e9142ca5636b3537762	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-4900000000-84f9b68467e23b1b2be6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl acetate EI-B (Non-derivatized)	splash10-0a4i-1900000000-20ee4619821736a9315b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Tolyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-8900000000-3ba6441286c265e3bf13	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Tolyl acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Tolyl acetate 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 - p-Tolyl acetate 10V, Positive-QTOF	splash10-0udi-0900000000-a6dd8dea636718b76d49	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 20V, Positive-QTOF	splash10-0pb9-1900000000-cabc72a995edd08e4292	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 40V, Positive-QTOF	splash10-0a6r-9400000000-abf6f090e016fc954f2a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 10V, Negative-QTOF	splash10-052b-0900000000-ce78f59a78db591cbb6a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 20V, Negative-QTOF	splash10-0a4j-0900000000-af452b60b226fd5f3749	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 40V, Negative-QTOF	splash10-0a4i-6900000000-69c7f20dc23dd16cd656	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 10V, Negative-QTOF	splash10-0002-0900000000-52536ea1b2265fd6cc39	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 20V, Negative-QTOF	splash10-0a4i-0900000000-c0f2170501c74d6cb276	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 40V, Negative-QTOF	splash10-0a4i-6900000000-c01ee153ab9e12a44918	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 10V, Positive-QTOF	splash10-0zfr-2900000000-aea7f1920cfb7fb64718	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 20V, Positive-QTOF	splash10-0536-9600000000-dd7d27b2a6ae89d7af72	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl acetate 40V, Positive-QTOF	splash10-0fbc-9000000000-d44626cd3d07f0a92d71	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

Cytoplasm
Extracellular

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

FDB008790

KNApSAcK ID

Not Available

Chemspider ID

21106001

KEGG Compound ID

C01963

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8797

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1003891

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 p-Tolyl acetate (HMDB0032075)

MOL for HMDB0032075 (p-Tolyl acetate)

3D MOL for HMDB0032075 (p-Tolyl acetate)

3D SDF for HMDB0032075 (p-Tolyl acetate)

3D-SDF for HMDB0032075 (p-Tolyl acetate)

PDB for HMDB0032075 (p-Tolyl acetate)

3D PDB for HMDB0032075 (p-Tolyl acetate)

SMILES for HMDB0032075 (p-Tolyl acetate)

INCHI for HMDB0032075 (p-Tolyl acetate)

Structure for HMDB0032075 (p-Tolyl acetate)

3D Structure for HMDB0032075 (p-Tolyl acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra