AFCDB: Methyl salicylate (FDB012459)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:11 UTC

Update date

2020-09-17 15:30:14 UTC

Primary ID

FDB012459

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methyl salicylate

Description

Methyl salicylate or methyl 2-hydroxybenzoate, 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. Methyl 2-hydroxybenzoate, a methyl ester of salicylic acid, is a neutral compound. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of a mint and with a peppermint, and wintergreen taste. It is a naturally occurring organic compound in many species of plants, particularly wintergreens. Methyl 2-hydroxybenzoate is found in highest concentrations in hyssops and bilberries and was detected in sour cherries, tamarinds, garden tomato (var.), black elderberries, and mandarin orange (clementine, tangerine). This could make methyl 2-hydroxybenzoate a potential biomarker for the consumption of these foods. It is also present in wines (PMID: 31500198; PMID: 31500198), tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry ( PMID: 31608465), papaya and plum. It is an anti-herbivore used by some plants to recruit beneficial insects (PMID: 15537163). It is used as a fragrance and is used in foods such as chewing gum and mints and in beverages. It is a topical analgesic added to liniments (such as Bengay) where it acts as a counter-irritant to relieve joint and muscle pain. As methyl salicyclate is metabolized to salicyclate, it is a potentially toxic compound, particularly to children or to adults who excessive overuse such liniments.

CAS Number

119-36-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.73 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.32	ChemAxon
logS	-1.4	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	2	ChemAxon
Refractivity	40.06 m³·mol⁻¹	ChemAxon
Polarizability	14.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H8O3

IUPAC name

methyl 2-hydroxybenzoate

InChI Identifier

InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3

InChI Key

OSWPMRLSEDHDFF-UHFFFAOYSA-N

Isomeric SMILES

COC(=O)C1=CC=CC=C1O

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

Classification

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
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

salicylates (CHEBI:31832 )
benzoate ester (CHEBI:31832 )
a small molecule (CPD-6442 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Biofluid and excreta:

Urine

Role

Industrial application:

Personal care products

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 63.15%; H 5.30%; O 31.55%	DFC
Melting Point	Mp -8.6°	DFC
Boiling Point	Bp12 101°	DFC
Experimental Water Solubility	0.7 mg/mL at 30 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.55	SANGSTER (1994)
Experimental pKa	pKa 9.87 (20°, 0.1M NaClO4)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d18.54 1.85	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9800000000-1d56d6cf07db519b50e2	2014-09-20	View Spectrum
GC-MS	Methyl salicylate, non-derivatized, GC-MS Spectrum	splash10-00dl-9800000000-4c121b87ee97a30f4150	Spectrum
GC-MS	Methyl salicylate, non-derivatized, GC-MS Spectrum	splash10-00dl-9800000000-aeff759175e190d33827	Spectrum
GC-MS	Methyl salicylate, non-derivatized, GC-MS Spectrum	splash10-00dl-9700000000-8449a003796d4c61d429	Spectrum
GC-MS	Methyl salicylate, non-derivatized, GC-MS Spectrum	splash10-00dl-9800000000-4c121b87ee97a30f4150	Spectrum
GC-MS	Methyl salicylate, non-derivatized, GC-MS Spectrum	splash10-00dl-9800000000-aeff759175e190d33827	Spectrum
GC-MS	Methyl salicylate, non-derivatized, GC-MS Spectrum	splash10-00dl-9700000000-8449a003796d4c61d429	Spectrum
Predicted GC-MS	Methyl salicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-5900000000-bb69ba7d9fb7889830b6	Spectrum
Predicted GC-MS	Methyl salicylate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-6920000000-3af2acf054d451df9493	Spectrum
Predicted GC-MS	Methyl salicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fk9-3900000000-e2029bf3c75775175ff3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0udi-0900000000-68100343194ca59dc3dc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0udi-0900000000-685742c82233f695b1f9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0uk9-0900000000-6b4261227c07f3f37829	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0fk9-0900000000-d947b63ba1f404e65847	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00di-0900000000-cef75bde9d9688c24943	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00di-0900000000-619ac91f6d02cca22e34	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00di-0900000000-972c6897098e7099014b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-00di-0900000000-7adc31a6192a35776d77	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-00di-0900000000-4409a163b77175958dad	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00di-1900000000-e227574efc1f513f782e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-00di-3900000000-698a94aee209f31a1b16	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-01b9-9600000000-940f844a43e36507f542	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-014i-9200000000-a2caed2cb41617423174	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-014i-9000000000-be109281c3eb1b276861	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-00di-0900000000-9e24206fc4e0bc22769a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0006-9000000000-e886631a9ef343795dc0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-ddc0fb8a40062ab7c744	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00di-0900000000-85d6f511342ec3ef1f61	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-eba52e49290e16ea60c0	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0900000000-684f1c8a3cf324183257	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-9300000000-a594ffaab84fc15a2edc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-76d5fc81bafad7c2222c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-dae7a80af6333acd66fc	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-9600000000-09304803bc773495c704	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34172

CRC / DFC (Dictionary of Food Compounds) ID

HHB30-H:HHB30-H

EAFUS ID

2495

Dr. Duke ID

METHYL-SALICYLATE|SALICYLIC-ACID-METHYL-ESTER

BIGG ID

Not Available

KNApSAcK ID

C00030767

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

119-36-8

GoodScent ID

rw1008471

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anaphrodisiac			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti pyretic	35493	A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.	DUKE
anti radicular			DUKE
anti rheumatalgic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti tartar			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
carminative			DUKE
counterirritant			DUKE
dentifrice			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
herpetifuge	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
Insectiphile	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
peppermint	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
wintergreen	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Methyl salicylate (FDB012459)

Structure for FDB012459 (Methyl salicylate)