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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:31:21 UTC

Update Date

2023-02-21 17:23:35 UTC

HMDB ID

HMDB0033761

Secondary Accession Numbers

HMDB33761

Metabolite Identification

Common Name

4-Methoxybenzyl acetate

Description

4-Methoxybenzyl acetate, also known as anisyl acetate, belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. 4-Methoxybenzyl acetate is a sweet, almond, and balsam tasting compound. 4-Methoxybenzyl acetate has been detected, but not quantified in, fruits and herbs and spices. This could make 4-methoxybenzyl acetate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Methoxybenzyl acetate.

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      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   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  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   12                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    9   13                                                       
CONECT    8    1   11   13                                                  
CONECT    9    3    4    7                                                  
CONECT   10    5    6   12                                                  
CONECT   11    8                                                            
CONECT   12    2   10                                                       
CONECT   13    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methoxybenzyl acetic acid	Generator
Anisyl acetate	MeSH
4-Methoxybenzenemethanol, acetate	HMDB
4-Methoxybenzenenemethyl acetate	HMDB
Acetic acid P-methoxybenzyl ester	HMDB
Anisyl acetate, P-isomer	HMDB
Benzenemethanol, 4-methoxy-, 1-acetate	HMDB
Benzenemethanol, 4-methoxy-, acetate	HMDB
Benzyl alcohol, P-methoxy-, acetate	HMDB
Benzyl alcohol, P-methoxy-, acetate (8ci)	HMDB
Cassie ketone	HMDB
FEMA 2098	HMDB
P-Methoxybenzyl acetate	HMDB
P-Methoxybenzyl alcohol acetate	HMDB
(4-Methoxyphenyl)methyl acetic acid	Generator

Chemical Formula

C₁₀H₁₂O₃

Average Molecular Weight

180.2005

Monoisotopic Molecular Weight

180.07864425

IUPAC Name

(4-methoxyphenyl)methyl acetate

Traditional Name

(4-methoxyphenyl)methyl acetate

CAS Registry Number

104-21-2

SMILES

COC1=CC=C(COC(C)=O)C=C1

InChI Identifier

InChI=1S/C10H12O3/c1-8(11)13-7-9-3-5-10(12-2)6-4-9/h3-6H,7H2,1-2H3

InChI Key

HFNGYHHRRMSKEU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carboxylic ester (CHEBI:86743 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033761)
Cytoplasm (HMDB: HMDB0033761)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033761)

Source

Exogenous

Food

Food (HMDB: HMDB0033761)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033761)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033761)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	84 °C	Not Available
Boiling Point	137.00 °C. @ 12.00 mm Hg	The Good Scents Company Information System
Water Solubility	782.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.887 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	2.2	ALOGPS
logP	1.49	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.49 m³·mol⁻¹	ChemAxon
Polarizability	19.05 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]+	142.134	31661259
DarkChem	[M-H]-	140.612	31661259
DeepCCS	[M+H]+	144.326	30932474
DeepCCS	[M-H]-	140.498	30932474
DeepCCS	[M-2H]-	178.204	30932474
DeepCCS	[M+Na]+	153.743	30932474
AllCCS	[M+H]+	138.9	32859911
AllCCS	[M+H-H2O]+	134.7	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	144.0	32859911
AllCCS	[M-H]-	141.3	32859911
AllCCS	[M+Na-2H]-	142.3	32859911
AllCCS	[M+HCOO]-	143.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methoxybenzyl acetate	COC1=CC=C(COC(C)=O)C=C1	2175.0	Standard polar	33892256
4-Methoxybenzyl acetate	COC1=CC=C(COC(C)=O)C=C1	1421.0	Standard non polar	33892256
4-Methoxybenzyl acetate	COC1=CC=C(COC(C)=O)C=C1	1463.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-4900000000-60ea4405cfb2f971c2dd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-5900000000-085e2f064c20eae3deb2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-1900000000-158d3ed1444b4191bc5c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-7900000000-30a71b31d69064484197	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-4900000000-60ea4405cfb2f971c2dd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-5900000000-085e2f064c20eae3deb2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-1900000000-158d3ed1444b4191bc5c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methoxybenzyl acetate EI-B (Non-derivatized)	splash10-00di-7900000000-30a71b31d69064484197	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxybenzyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9700000000-4ff8ed1586ef7fbda935	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxybenzyl 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 - 4-Methoxybenzyl acetate 10V, Positive-QTOF	splash10-001i-0900000000-e6e0d4007d8cd8ad5377	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 20V, Positive-QTOF	splash10-001i-1900000000-bd70bfff756ff82607a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 40V, Positive-QTOF	splash10-0006-9800000000-b47a093be4637bc60f11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 10V, Negative-QTOF	splash10-004i-2900000000-d5377ab68bb869335140	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 20V, Negative-QTOF	splash10-004i-2900000000-edc6b18cddc0dd80b7d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 40V, Negative-QTOF	splash10-0006-9700000000-7654fc3bc3f7e66b9aa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 10V, Positive-QTOF	splash10-00di-3900000000-38be237e8c042073bd27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 20V, Positive-QTOF	splash10-00di-7900000000-4e918a5d918c62a45260	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 40V, Positive-QTOF	splash10-004l-9100000000-cc2d7e055213a471ffdc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 10V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybenzyl acetate 40V, Negative-QTOF	splash10-0abc-9200000000-93371c7927d83c541924	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

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

FDB011898

KNApSAcK ID

Not Available

Chemspider ID

7410

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7695

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1001292

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-Methoxybenzyl acetate (HMDB0033761)

MOL for HMDB0033761 (4-Methoxybenzyl acetate)

3D MOL for HMDB0033761 (4-Methoxybenzyl acetate)

3D SDF for HMDB0033761 (4-Methoxybenzyl acetate)

3D-SDF for HMDB0033761 (4-Methoxybenzyl acetate)

PDB for HMDB0033761 (4-Methoxybenzyl acetate)

3D PDB for HMDB0033761 (4-Methoxybenzyl acetate)

SMILES for HMDB0033761 (4-Methoxybenzyl acetate)

INCHI for HMDB0033761 (4-Methoxybenzyl acetate)

Structure for HMDB0033761 (4-Methoxybenzyl acetate)

3D Structure for HMDB0033761 (4-Methoxybenzyl acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra