Methyl 3-(methylthio)propionate

Base Information

• Chemical Name: Methyl 3-(methylthio)propionate
• CAS No.: 13532-18-8
• Molecular Formula: C5H10O2S
• Molecular Weight: 134.199
• Hs Code.: 29309070
• European Community (EC) Number: 236-883-6
• NSC Number: 76415
• UNII: 28913SS9T9
• DSSTox Substance ID: DTXSID0047402
• Nikkaji Number: J121.902B
• Wikidata: Q27254289
• Metabolomics Workbench ID: 46513
• ChEMBL ID: CHEMBL119603
• Mol file: 13532-18-8.mol

Synonyms:Methyl 3-(methylthio)propionate;13532-18-8;Methyl 3-methylthiopropionate;Methyl 3-(methylthio)propanoate;methyl 3-methylsulfanylpropanoate;Propanoic acid, 3-(methylthio)-, methyl ester;Methyl-3-(methylthio)propionate;Methyl beta-methiopropionate;Methyl 3-(methylsulfanyl)propanoate;Propionic acid, 3-(methylthio)-, methyl ester;methyl 3-methylthiopropanoate;FEMA No. 2720;Methyl beta-methylthiopropionate;3-(Methylthio)propanoic acid methyl ester;Methyl beta-methylmercaptopropionate;Methyl 3-(methylmercapto)propionate;NSC 76415;METHYL3-(METHYLTHIO)PROPIONATE;UNII-28913SS9T9;Methyl-3-methylmercaptopropionate;Methyl .beta.-methylthiopropionate;EINECS 236-883-6;NSC-76415;Methyl .beta.-methylmercaptopropionate;28913SS9T9;AI3-36712;Methyl ester of 3-(methylthio)propanoic acid;3-(Methylthio)propionic Acid Methyl Ester;Methyl methylthiopropanoate;SCHEMBL857398;methyl-3-methyl thiopropionate;Methyl 3-Methylthio Propionate;Methyl-3-Methylthio Propionate;CHEMBL119603;methyl 3-methylsulanylpropanoate;DTXSID0047402;DMMJVMYCBULSIS-UHFFFAOYSA-;FEMA 2720;Methyl beta -methylthiopropionate;methyl-3-(methylthio) propionate;Benzofuran, 3-(1-methylethyl)-;CHEBI:173552;methyl 3-(methyl thio) propionate;NSC76415;METHYL (METHYLTHIO)PROPIONATE;Methyl beta -methylmercaptopropionate;METHYL-3-METHYLTHIOPROPIONATE;2-Methoxycarbonylethyl methyl sulfide;MFCD00008565;AKOS008902908;Methyl 3-(methylthio)propionate, 98%;AS-60592;METHYL-3-METHYLTHIOPROPIONATE [FCC];3-Methylsulfanyl-propionic acid methyl ester;CS-0128902;FT-0613800;M0862;METHYL 3-METHYLTHIOPROPIONATE [FHFI];E75865;Methyl 3-(methylthio)propionate, >=98%, FG;EN300-6488059;J-640412;J-800446;Q-100134;Propionic acid, 3-(methylthio)-, methyl ester (8CI);Q27254289

Chemical Property of Methyl 3-(methylthio)propionate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 0.735mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Boiling Point: 184.4 °C at 760 mmHg
• Flash Point: 72.2 °C
• PSA: 51.60000
• Density: 1.044 g/cm³
• LogP: 0.91250
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 134.04015073
• Heavy Atom Count: 8
• Complexity: 72.8

Purity/Quality:

99% ^*data from raw suppliers

Methyl 3-(Methylthio)propionate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CCSC
• Description: Methyl 3-Methylthiopropionate is a faint yellow liquid with pineapple organoleptic properties, which belongs to the family of Thia Fatty Acids. It can be isolated from pineapple, melon, naranjila fruit and white wine or obtained by insertion of a sulfur atom at specific positions in the chain. It mostly serves as a flavor and fragrance without safety concern at current levels of intake. Besides, it serves as a additive applied in cigarettes, which was listed in the List of 599 Additives in Cigarettes submitted to the United States Department of Health and Human Services in April 1994. Methyl 3-methylthiopropionate has an extremely powerful, penetrating, sweet odor. It is onion-like at high concentrations with a sweet pineapple flavor at high dilutions. Obtained in 84% yields by reacting CH2 = CH — CO — OCH3 with CH3SH; the corresponding acid also has been synthesized.
• Uses: Methyl 3-(methylthio)propionate was used to prepare 3-methiolpropionate(MMPA) to study the demethylation of Dimethylsulfoniopropionate and MMPA to 3-mercaptopropionate by aerobic marine bacterium. Methyl 3-(methylthio)propionate was used to prepare 3-(Methylthio)propionic acid to examine the methionine catabolism by Lactococci by 13C Nuclear Magnetic Resonance and Gas Chromatography.

Technology Process of Methyl 3-(methylthio)propionate

There total 21 articles about Methyl 3-(methylthio)propionate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3-(methylsulfinyl)propionic acid methyl ester → methyl 3-(methylthio)propionate (13532-18-8)

Guidance literature:

With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; triphenylphosphine; In dichloromethane; at 20 ℃; for 0.0166667h;

DOI:10.1016/j.crci.2013.11.006

Reference yield: 84.0%

Methyl 3-mercaptopropionate (2935-90-2) + methyl iodide (74-88-4) → methyl 3-(methylthio)propionate (13532-18-8)

Guidance literature:

With potassium carbonate; In acetone; at 25 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.202002265

Reference yield: 81.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + methyl iodide (74-88-4) → methyl 3-(methylthio)propionate (13532-18-8)

Guidance literature:

methyl iodide; With urea/choline chloride eutectic salt; thiourea; at 60 ℃; Green chemistry;

acrylic acid methyl ester; With sodium hydroxide; In water; at 20 ℃; for 1.33333h; Green chemistry;

DOI:10.1016/j.tetlet.2014.01.104

upstream raw materials:

methylthiol

Methyl 3-bromopropionate

acrylic acid methyl ester

methyl 3-chloropropionate

Downstream raw materials:

3-methanesulfonyl-propionic acid methyl ester

(2-methoxycarbonyl-ethyl)-dimethyl sulfonium ; iodide

CCl₃O₂^(1-)

3-(methylthio)propanamide

Refernces

• 1、 Adlington, Robert M.,Baldwin, Jack E.,Crouch, Nicholas P.,Lee, Meng-Huee,MacKinnon, Colin H.. "Identification and stereochemistry of the product of 4-HPPD catalyzed oxidation of the ketoacid of methionine". . p. 2003 - 2006. Retrieved 1996.
• 2、 Mahling, Sabine,Asmus, Klaus-Dieter,Glass, Richard S.,Hojjatie, Massoud,Wilson, George S.. "Neighboring Group Participation in Radicals: Pulse Radiolysis Studies on Radicals with Sulfur-Oxygen Interaction". . p. 3717 - 3724. Retrieved 1987.
• 3、 Pan, Dandan,Xu, Shasha,Tian, Qingqiang,Li, Yahui. "Pd-Catalyzed Intermolecular Transthiolation of Ar-OTf Using Methyl 3-(Methylthio) Propanoate as a Thiol Surrogate". supporting information. p. 4616 - 4619. Retrieved 2021/09/10.
• 4、 Burkhardt, Immo,Lauterbach, Lukas,Brock, Nelson L.,Dickschat, Jeroen S.. "Chemical differentiation of three DMSP lyases from the marine: Roseobacter group". supporting information. p. 4432 - 4439. Retrieved 2017/07/10.