3-Mercapto-2-methylpentan-1-ol

Base Information

• Chemical Name: 3-Mercapto-2-methylpentan-1-ol
• CAS No.: 227456-27-1
• Molecular Formula: C₆H₁₄OS
• Molecular Weight: 134.243
• European Community (EC) Number: 434-900-3,607-151-7,927-385-6
• UNII: 7XRY329G5S
• DSSTox Substance ID: DTXSID20870267
• Nikkaji Number: J1.340.022I
• Wikidata: Q27268990
• Metabolomics Workbench ID: 46724
• Mol file: 227456-27-1.mol

Synonyms:3-mercapto-2-methylpentan-1-ol

Chemical Property of 3-Mercapto-2-methylpentan-1-ol

Chemical Property:

• Vapor Pressure: 0.0612mmHg at 25°C
• Refractive Index: 1.472
• Boiling Point: 204.968 °C at 760 mmHg
• PKA: 10.50±0.10(Predicted)
• Flash Point: 77.762 °C
• PSA: 59.03000
• Density: 0.96 g/cm³
• LogP: 1.32320
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 134.07653624
• Heavy Atom Count: 8
• Complexity: 56.5

Purity/Quality:

99% ^*data from raw suppliers

3-Mercapto-2-methyl-1-pentanol (mixture of diastereoisomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(C)CO)S
• Sources: Initially detected in complex thermally processed flavors and isolated from raw onions. More concentrated in cooked onions, particularly in certain varieties.
• Uses: Detected by the human odorant receptor OR2M3 with high specificity and sensitivity. Important in shaping the overall flavor of foods like gravies. Plays a role in food and complementary medicine.
• References: [1] Modeling by statistical physics and interpretation of the olfactory process of the two enantiomers 3-mercapto-2-methylbutan-1-ol and 3-mercapto-2-methylpentan-1-ol on the OR2M3 human olfactory receptor; DOI 10.1016/j.ijbiomac.2023.124896; [2] OR2M3: A Highly Specific and Narrowly Tuned Human Odorant Receptor for the Sensitive Detection of Onion Key Food Odorant 3-Mercapto-2-methylpentan-1-ol; DOI 10.1093/chemse/bjw118; [3] Human Oral Sensitivity to and Taste Modulation by 3-Mercapto-2-Methylpentan-1-ol; DOI 10.1007/s12078-022-09295-w

Technology Process of 3-Mercapto-2-methylpentan-1-ol

There total 3 articles about 3-Mercapto-2-methylpentan-1-ol 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:

3-(acetylthio)-2-methylpentanal (22236-42-6) → 3-mercapto-2-methylpentan-1-ol (227456-27-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 0.5h;

DOI:10.1021/jf9908291

Reference yield:

(E)-2-methylpent-2-enal (623-36-9) → 3-mercapto-2-methylpentan-1-ol (227456-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine / 18 h / 20 °C

2: LiAlH₄ / diethyl ether

With piperidine; lithium aluminium tetrahydride; In diethyl ether; 1: Michael addition;

DOI:10.1021/jf0498968

Reference yield:

2-methyl-2-pentenal (14250-96-5,16958-22-8,623-36-9) → 3-mercapto-2-methylpentan-1-ol (227456-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine / 18 h / 20 °C

2: LiAlH₄ / diethyl ether / 0.5 h / 20 °C

With piperidine; lithium aluminium tetrahydride; In diethyl ether; 1: Addition / 2: Reduction;

DOI:10.1021/jf9908291

upstream raw materials:

3-(acetylthio)-2-methylpentanal

(E)-2-methylpent-2-enal

2-methyl-2-pentenal

Refernces

• 1、 Granvogl, Michael,Christlbauer, Monika,Schieberle, Peter. "Quantitation of the Intense Aroma Compound 3-Mercapto-2-methylpentan-1-ol in Raw and Processed Onions (Allium cepa) of Different Origins and in Other Allium Varieties Using a Stable Isotope Dilution Assay". . p. 2797 - 2802. Retrieved 2004.