4-Mercapto-4-methyl-2-pentanone

Base Information

• Chemical Name: 4-Mercapto-4-methyl-2-pentanone
• CAS No.: 19872-52-7
• Molecular Formula: C6H12OS
• Molecular Weight: 132.227
• Hs Code.: 2930909090
• European Community (EC) Number: 243-386-8
• UNII: 9524RG5ZQL
• DSSTox Substance ID: DTXSID8051839
• Nikkaji Number: J104.455I
• Wikipedia: 4-Mercapto-4-methyl-2-pentanone
• Wikidata: Q27147464
• Metabolomics Workbench ID: 5695
• Mol file: 19872-52-7.mol

Synonyms:19872-52-7;4-Mercapto-4-methyl-2-pentanone;4-Mercapto-4-methylpentan-2-one;2-Pentanone, 4-mercapto-4-methyl-;4-methyl-4-sulfanylpentan-2-one;4-methyl-4-mercapto-2-pentanone;4-Methyl-4-mercaptopentan-2-one;4-Methyl-4-thiolpentan-2-one;4-Methyl-4-sulfanyl-2-pentanone;4-Sulfanyl-4-methylpentan-2-one;4-Sulphanyl-4-methylpentan-2-one;4-Methyl-4-mercapto-pentan-2-one;EINECS 243-386-8;UNII-9524RG5ZQL;9524RG5ZQL;FEMA3997;4-Mercapto-4-methyl-pentan-2-one;4-MMP;SCHEMBL869584;DTXSID8051839;FEMA NO. 3997;CHEBI:77856;2-pentanona, 4-mercapto-4-metil-;LMFA12000335;MFCD00085208;AKOS006283682;2-MERCAPTO-2-METHYLPENTAN-4-ONE;AS-17349;FT-0600299;M3271;4-methyl-4-mercaptopentan-2-one, AldrichCPR;D95275;4-4 - mercaptoacetic - methyl ketone - 2 - e;4-MERCAPTO-4-METHYL-2-PENTANONE [FHFI];A925051;J-012835;Q27147464

Chemical Property of 4-Mercapto-4-methyl-2-pentanone

Chemical Property:

• Vapor Pressure: 0.843mmHg at 25°C
• Refractive Index: 1.456
• Boiling Point: 181.7 °C at 760 mmHg
• PKA: 10.32±0.25(Predicted)
• Flash Point: 63.7 ºC
• PSA: 55.87000
• Density: 0.952 g/cm³
• LogP: 1.67390
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 132.06088618
• Heavy Atom Count: 8
• Complexity: 96.7

Purity/Quality:

99% ^*data from raw suppliers

4-Mercapto-4-methyl-2-pentanone ^*data from reagent suppliers

Safty Information:

• Statements: 10-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(C)(C)S
• Chemical Composition and Structure: 4-Mercapto-4-methyl-2-pentanone (4MMP) is an alkylthiol compound consists of a five-carbon chain with a methyl group at the 4-position and a mercapto group attached to the second carbon atom.
• Uses: 4MMP is known for its aroma, contributing to flavors such as box tree and black currant in wine. It is released from its precursors by microbial cysteine-S-conjugate β-lyases. Microbial cell extracts containing β-lyases can convert thiol precursors into 4MMP. This conversion yields sulfur-containing aroma compounds that enhance the aromatic complexity of wine.
• Production Methods: The precursor of 4MMP, cysteine-conjugate of 4MMP, can be synthesized using chemical methods. In addition, microbial cell extracts containing β-lyases, particularly from bacteria like Shewanella putrefaciens, are used to convert thiol precursors into 4MMP.
• References: [1] Conversion of a Thiol Precursor into Aroma Compound 4-mercapto-4-methyl-2-pentanone Using Microbial Cell Extracts; DOI 10.3390/fermentation7030129; [2] Direct accurate analysis of cysteinylated and glutathionylated precursors of 4-mercapto-4-methyl-2-pentanone and 3-mercaptohexan-1-ol in must by ultrahigh performance liquid chromatography coupled to mass spectrometry; DOI 10.1016/j.aca.2014.01.004; [3] Automated Analysis of 4-Mercapto-4-methyl-2-pentanone in Japanese Green Tea (Sen-cha) by Headspace Solid-Phase Microextraction and Gas Chromatography with Mass Spectrometric Determination; DOI 10.3136/fstr.16.59

Technology Process of 4-Mercapto-4-methyl-2-pentanone

There total 14 articles about 4-Mercapto-4-methyl-2-pentanone 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: 70.0%

4-methyl-pent-3-en-2-one (141-79-7) → 4-mercapto-4-methylpentan-2-one (19872-52-7)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; HSiPh₃; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jf0004715

Reference yield:

L-Cysteine (52-90-4) → 3,3,5,5-tetramethyl-1,2,4-trithiolane (38348-31-1) + 4-methyl-pent-3-en-2-one (141-79-7) + 5-Hexen-2-one (109-49-9) + 4-mercapto-4-methylpentan-2-one (19872-52-7) + 4-Hydroxy-4-methyl-2-pentanone (123-42-2) + 4-methoxy-4-methylpentan-2-one (107-70-0) + carbon dioxide (124-38-9,18923-20-1) + carbon monoxide (201230-82-2)

Guidance literature:

With air; at 30 - 180 ℃;

DOI:10.3390/molecules201219843

Reference yield:

4-(dodecylsulfanyl)-4-methylpentan-2-one → 4-methyl-pent-3-en-2-one (141-79-7) + 4-mercapto-4-methylpentan-2-one (19872-52-7) + Dodecanal (112-54-9)

Guidance literature:

With air; at 20 ℃;

DOI:10.1002/hlca.202100135

upstream raw materials:

4-methyl-pent-3-en-2-one

2,4,4-Trimethylthiet

acetone

ammonia

Downstream raw materials:

4-methyl-4-phenylsulfanyl-pentan-2-one

4-methyl-4-phenyldiazenosulfanyl-pentan-2-one

4,6,6-trimethyl-2-phenyl-5,6-dihydro-2H-[1,3]thiazine

2-(4,6,6-trimethyl-5,6-dihydro-2H-[1,3]thiazin-2-yl)-phenol