Showing Compound Ethyl 3-(methylthio)propanoate (FDB020145)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:49 UTC

Update date

2019-11-26 03:18:32 UTC

Primary ID

FDB020145

Secondary Accession Numbers

FDB003795

Chemical Information

FooDB Name

Ethyl 3-(methylthio)propanoate

Description

Ethyl 3-(methylthio)propanoate, also known as ethyl methyl mercaptopropionate, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Ethyl 3-(methylthio)propanoate is a fruity, metallic, and pineapple tasting compound. Ethyl 3-(methylthio)propanoate is found, on average, in the highest concentration within pineapples (Ananas comosus). Ethyl 3-(methylthio)propanoate has also been detected, but not quantified in, several different foods, such as alcoholic beverages, asian pears (Pyrus pyrifolia), fruits, and milk and milk products. This could make ethyl 3-(methylthio)propanoate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ethyl 3-(methylthio)propanoate.

CAS Number

13327-56-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-(Methylthio)propanoic acid ethyl ester	ChEBI
Ethyl 3-(methylmercapto)propionate	ChEBI
Ethyl methyl mercaptopropionate	ChEBI
3-(Methylthio)propanoate ethyl ester	Generator
Ethyl 3-(methylmercapto)propionic acid	Generator
Ethyl methyl mercaptopropionic acid	Generator
Ethyl 3-(methylthio)propanoic acid	Generator
Ethyl 3-(methylthio)propionate	ChEBI
Ethyl 3-methylmercaptopropionate	ChEBI
Ethyl 3-(methylthio)propionic acid	Generator
Ethyl 3-methylmercaptopropionic acid	Generator
3-(methylthio)Propionic acid ethylester	HMDB
Ethyl 3-(methylsulfanyl)propanoate	HMDB
Ethyl 3-methylthiopropanoate	HMDB
Ethyl beta -methylthiopropionate	HMDB
Ethyl beta-methylthiopropionate	HMDB
Ethyl methylthiopropanoate	HMDB
FEMA 3343	HMDB
Propanoic acid, 3-(methylthio)-, ethyl ester	HMDB
Propionic acid, 3-(methylthio)-, ethyl ester	HMDB
Ethyl 3-(methylthio)propanoate	ChEBI
Ethyl 3-methylthiopropionic acid	Generator
3-(Methylthio)propionic acid ethylester	biospider

Predicted Properties

Property	Value	Source
Water Solubility	5.3 g/L	ALOGPS
logP	1.38	ALOGPS
logP	1.34	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-7	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	5	ChemAxon
Refractivity	39.24 m³·mol⁻¹	ChemAxon
Polarizability	16.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H12O2S

IUPAC name

ethyl 3-(methylsulfanyl)propanoate

InChI Identifier

InChI=1S/C6H12O2S/c1-3-8-6(7)4-5-9-2/h3-5H2,1-2H3

InChI Key

YSNWHRKJEKWJNY-UHFFFAOYSA-N

Isomeric SMILES

CCOC(=O)CCSC

Average Molecular Weight

148.223

Monoisotopic Molecular Weight

148.055800318

Classification

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:87503 )
organosulfur compound (CHEBI:87503 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 48.62%; H 8.16%; O 21.59%; S 21.63%	DFC
Melting Point	Not Available
Boiling Point	Bp18 88°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	beta-Methylthiopropionic acid ethyl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fb9-9300000000-029e31417dd68f480b60	Spectrum
Predicted GC-MS	beta-Methylthiopropionic acid ethyl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-Methylthiopropionic acid ethyl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6t-1900000000-5bf8b1d6ee6320d4c1b4	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfs-9700000000-8bcaf49d26d088c50af9	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056s-9100000000-e0f8ca1ee495f433791b	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9200000000-7645bab4e5fe8392cce3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9100000000-a4d3fefdf137fe9f1a0f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-cce896b87192798ff9bf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9300000000-5fb908dda705dda95183	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-fa0dccf82eb5be566ca7	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0w90-5900000000-49128a20cce7699fb3a6	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9100000000-1ba654d4162c188e7c9e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-9000000000-e1911524715c4e6b894a	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

55501

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

61592

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40413

CRC / DFC (Dictionary of Food Compounds) ID

HKQ35-E:MKW85-A

EAFUS ID

1270

Dr. Duke ID

ETHYL-BETA-METHYLTHIOPROPIONATE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1008241

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sulfury	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
metallic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pineapple	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ripe	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pulpy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tomato	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.