Whiskey lactone

Base Information

• Chemical Name: Whiskey lactone
• CAS No.: 39212-23-2
• Molecular Formula: C9H16O2
• Molecular Weight: 156.225
• Hs Code.: 2932209090
• European Community (EC) Number: 254-357-4
• DSSTox Substance ID: DTXSID90865948
• Nikkaji Number: J47.448G
• Metabolomics Workbench ID: 46918
• Mol file: 39212-23-2.mol

Synonyms:beta-methyl-gamma-octalactone

Chemical Property of Whiskey lactone

Chemical Property:

• Vapor Pressure: 0.027mmHg at 25°C
• Refractive Index: n20/D 1.4454(lit.)
• Boiling Point: 246.5 °C at 760 mmHg
• Flash Point: 95.6 °C
• PSA: 26.30000
• Density: 0.936 g/cm³
• LogP: 2.12820
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 156.115029749
• Heavy Atom Count: 11
• Complexity: 143

Purity/Quality:

99% ^*data from raw suppliers

Whiskey lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1C(CC(=O)O1)C

Technology Process of Whiskey lactone

There total 107 articles about Whiskey lactone 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: 97.0%

5-Butyl-2-ethoxy-4-methyl-tetrahydrofuran (141406-32-8,141406-33-9) → trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (87433-77-0,99530-35-5,39212-23-2,39638-67-0,55013-32-6,80041-00-5,80041-01-6,89163-43-9,105015-53-0,105119-22-0)

Guidance literature:

With Jones reagent; In acetone; for 0.05h; Irradiation;

DOI:10.1080/00397919208021096

Reference yield: 95.0%

1-(1,3-Dithianylidene)-2-methyl-3-heptanol (102587-17-7,106501-07-9) → trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (87433-77-0,99530-35-5,39212-23-2,39638-67-0,55013-32-6,80041-00-5,80041-01-6,89163-43-9,105015-53-0,105119-22-0)

Guidance literature:

With mercury dichloride; In methanol; water; for 5h; Heating;

DOI:10.1021/jo00381a026

Reference yield: 87.0%

threo-3-methyloctane-1,4-diol → trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (87433-77-0,99530-35-5,39212-23-2,39638-67-0,55013-32-6,80041-00-5,80041-01-6,89163-43-9,105015-53-0,105119-22-0)

Guidance literature:

With horse liver alcohol dehydrogenase; NADP; Flavin mononucleotide; In aq. buffer; for 120h; Reagent/catalyst; Enzymatic reaction;

DOI:10.1016/j.foodchem.2013.02.106

upstream raw materials:

pentanal

(Z)-2-Dimethylamino-pent-2-enenitrile

(4S,5R)-3,3-Dichloro-5-(3,4-dimethoxy-phenyl)-4-methyl-5-p-tolylsulfanyl-dihydro-furan-2-one

1,1-dimethoxyethylene

Downstream raw materials:

C₄H₄O₂(CH₂HgBr)(CH₂CH₂CH₂CH₃)

CH₃OOCCH₂CH(CH₂HgBr)CH(OOCCF₃)CH₂CH₂CH₂CH₃

(4R,5S)-trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone

(3S,4S)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester

Refernces

• 1、 Kumru, Ceyda,Classen, Thomas,Pietruszka, J?rg. "Enantioselective, Catalytic One-Pot Synthesis of γ-Butyrolactone-Based Fragrances". . p. 4931 - 4940. Retrieved 2018/10/15.
• 2、 Boratyński, Filip,Smuga, Ma?gorzata,Wawrzeńczyk, Czes?aw. "Lactones 42. Stereoselective enzymatic/microbial synthesis of optically active isomers of whisky lactone". . p. 419 - 427. Retrieved 2013/10/08.