NP-MRD: Showing NP-Card for Ethyl salicylate (NP0000696)

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Record Information

Version

2.0

Created at

2012-09-11 17:32:49 UTC

Updated at

2024-09-03 04:22:10 UTC

NP-MRD ID

NP0000696

Natural Product DOI

https://doi.org/10.57994/2762

Secondary Accession Numbers

None

Natural Product 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 SDF 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

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	HMDB
2-Carboethoxyphenol	HMDB
2-Ethoxycarbonylphenol	HMDB
O-Hydroxybenzoic acid ethyl ester	HMDB
Ethyl salicylate	MeSH

Chemical Formula

C₉H₁₀O₃

Average Mass

166.1739 Da

Monoisotopic Mass

166.06299 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Castanopsis cuspidata		LOTUS database
Dactylanthus taylorii		LOTUS database
Decalepis hamiltonii		LOTUS database
Geum heterocarpum		LOTUS database
Paeonia lactiflora		LOTUS database
Paeonia suffruticosa		LOTUS database
Picea abies		LOTUS database
Polygala senega		LOTUS database
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Vanilla planifolia Jacks.		LOTUS database

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

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	1.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.95	Not Available

Predicted 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

External Links

HMDB ID

HMDB0029817

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001028

KNApSAcK ID

Not Available

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

Good Scents ID

Not Available

References

General References

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

Showing NP-Card for Ethyl salicylate (NP0000696)

MOL for NP0000696 (Ethyl salicylate)

3D MOL for NP0000696 (Ethyl salicylate)

3D SDF for NP0000696 (Ethyl salicylate)

3D-SDF for NP0000696 (Ethyl salicylate)

PDB for NP0000696 (Ethyl salicylate)

3D PDB for NP0000696 (Ethyl salicylate)

SMILES for NP0000696 (Ethyl salicylate)

INCHI for NP0000696 (Ethyl salicylate)

Structure for NP0000696 (Ethyl salicylate)

3D Structure for NP0000696 (Ethyl salicylate)