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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:32:49 UTC

Update Date

2023-02-21 17:19:16 UTC

HMDB ID

HMDB0029817

Secondary Accession Numbers

HMDB29817

Metabolite Identification

Common Name

Ethyl salicylate

Description

Ethyl salicylate, also known as fema 2458 or mesotol, belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Ethyl salicylate is a sweet, balsam, and floral tasting compound. Ethyl salicylate has been detected, but not quantified, in several different foods, such as evergreen blackberries, alcoholic beverages, black elderberries, garden tomato, and fruits. Ethyl salicylate is the ester formed by the condensation of salicylic acid and ethanol. It is a clear liquid that is sparingly soluble in water, but soluble in alcohol and ether. It has a pleasant odor resembling wintergreen and is used in perfumery and artificial flavors.

Structure

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

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      12.560 -11.636   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.910 -10.075   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.235 -12.417   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.910 -11.636   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.235 -13.978   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.580 -12.417   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.910 -14.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.580 -13.978   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.924 -12.425   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.255 -11.657   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.553 -10.099   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.586 -12.426   0.000  0.00  0.00           C+0
CONECT    1    3    9   11                                                  
CONECT    2    4                                                            
CONECT    3    4    5    1                                                  
CONECT    4    2    3    6                                                  
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9   10    1                                                       
CONECT   10    9   12                                                       
CONECT   11    1                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl salicylic acid	Generator
2-Hydroxybenzoic acid ethyl ester	HMDB
2-Hydroxyethylbenzoic acid	HMDB
Benzoic acid, 2-hydroxy-, ethyl ester	HMDB
Benzoic acid, hydroxy-, ethyl ester	HMDB
Ethyl 2-hydroxybenzoate	HMDB
Ethyl hydroxybenzoate	HMDB
Ethyl O-hydroxybenzoate	HMDB
Ethyl salicyclate	HMDB
FEMA 2458	HMDB
Mesotol	HMDB
Methyl 2-hydroxybenzoate	HMDB
Methyl salicylate	HMDB
O-(Ethoxycarbonyl)phenol	HMDB
Sal ether	HMDB
Sal ethyl	HMDB
Salicyclic acid, ethyl ester	HMDB
Salicylic acid, ethyl ester	HMDB
Salicylic ether	HMDB
Salicylic ethyl ester	HMDB
Salotan	HMDB
Salstan	HMDB
Ethyl 2-hydroxybenzoic acid	Generator, HMDB
Ethyl salicylate	MeSH
2-Carboethoxyphenol	HMDB
2-Ethoxycarbonylphenol	HMDB
Ethyl o-hydroxybenzoate	HMDB
o-(Ethoxycarbonyl)phenol	HMDB
o-Hydroxybenzoic acid ethyl ester	HMDB

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

ethyl 2-hydroxybenzoate

Traditional Name

ethyl salicylate

CAS Registry Number

118-61-6

SMILES

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

InChI Identifier

InChI=1S/C9H10O3/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6,10H,2H2,1H3

InChI Key

GYCKQBWUSACYIF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029817)
Cell membrane (HMDB: HMDB0029817)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0029817)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029817)

Source

Endogenous

Endogenous (HMDB: HMDB0029817)

Plant

Plant (HMDB: HMDB0029817)

Exogenous

Food

Food (HMDB: HMDB0029817)

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0029817)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0029817)
Flavoring Agent (HMDB: HMDB0029817)

Biological role

Anti myalgic (HMDB: HMDB0029817)
Anti rheumatalgic (HMDB: HMDB0029817)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	1.3 °C	Not Available
Boiling Point	233.00 to 235.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	737.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.95	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.07 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.68	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.81 m³·mol⁻¹	ChemAxon
Polarizability	16.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.022	31661259
DarkChem	[M-H]-	134.04	31661259
DeepCCS	[M+H]+	136.366	30932474
DeepCCS	[M-H]-	132.706	30932474
DeepCCS	[M-2H]-	170.047	30932474
DeepCCS	[M+Na]+	145.585	30932474
AllCCS	[M+H]+	135.1	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.2	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	134.3	32859911
AllCCS	[M+Na-2H]-	135.4	32859911
AllCCS	[M+HCOO]-	136.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl salicylate	CCOC(=O)C1=C(O)C=CC=C1	1975.6	Standard polar	33892256
Ethyl salicylate	CCOC(=O)C1=C(O)C=CC=C1	1316.6	Standard non polar	33892256
Ethyl salicylate	CCOC(=O)C1=C(O)C=CC=C1	1312.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl salicylate,1TMS,isomer #1	CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C	1476.6	Semi standard non polar	33892256
Ethyl salicylate,1TBDMS,isomer #1	CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	1693.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl salicylate EI-B (Non-derivatized)	splash10-00di-5900000000-f5eb6e8bd07e0d734060	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl salicylate EI-B (Non-derivatized)	splash10-00xu-8900000000-86cbf27957a874eacf48	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl salicylate EI-B (Non-derivatized)	splash10-00di-6900000000-8e32263351a87a3cac48	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl salicylate EI-B (Non-derivatized)	splash10-00di-5900000000-f5eb6e8bd07e0d734060	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl salicylate EI-B (Non-derivatized)	splash10-00xu-8900000000-86cbf27957a874eacf48	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl salicylate EI-B (Non-derivatized)	splash10-00di-6900000000-8e32263351a87a3cac48	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-76416e68288f87d1b2fb	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl salicylate GC-MS (1 TMS) - 70eV, Positive	splash10-0006-3910000000-3ab2317224cf5004c30d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-6900000000-fbc256a2ef3e0b3ff3bb	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 10V, Positive-QTOF	splash10-014i-0900000000-c9c4fa6ec7edfa49b61d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 20V, Positive-QTOF	splash10-00xr-1900000000-ab4e08dfd3db7c5f59f3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 40V, Positive-QTOF	splash10-0uk9-9300000000-2532177974c69b27ce91	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 10V, Negative-QTOF	splash10-014i-2900000000-040861e4eb1b3cfbb0ae	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 20V, Negative-QTOF	splash10-014l-5900000000-b6232bbfa2f557c2f19e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 40V, Negative-QTOF	splash10-0006-9100000000-9c55ed111643f19b1e96	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 10V, Negative-QTOF	splash10-014i-1900000000-7f718c27c84b2f6b4fdb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 20V, Negative-QTOF	splash10-0006-9400000000-903c0dea5a38deb54126	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 40V, Negative-QTOF	splash10-0006-9000000000-a52f07348114f58d4ae0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 10V, Positive-QTOF	splash10-00di-1900000000-94ae43f33f856090e94c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 20V, Positive-QTOF	splash10-00dl-7900000000-b68bae8ef0f425dfe6f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl salicylate 40V, Positive-QTOF	splash10-006x-9300000000-9bb5545b3b4131fca7c8	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details

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

FDB001028

KNApSAcK ID

C00030767

Chemspider ID

21105897

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl salicylate

METLIN ID

Not Available

PubChem Compound

8365

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1001561

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Ethyl salicylate (HMDB0029817)

MOL for HMDB0029817 (Ethyl salicylate)

3D MOL for HMDB0029817 (Ethyl salicylate)

3D SDF for HMDB0029817 (Ethyl salicylate)

3D-SDF for HMDB0029817 (Ethyl salicylate)

PDB for HMDB0029817 (Ethyl salicylate)

3D PDB for HMDB0029817 (Ethyl salicylate)

SMILES for HMDB0029817 (Ethyl salicylate)

INCHI for HMDB0029817 (Ethyl salicylate)

Structure for HMDB0029817 (Ethyl salicylate)

3D Structure for HMDB0029817 (Ethyl salicylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra