Trans-3-Methyl-4-octanolide

Base Information

• Chemical Name: Trans-3-Methyl-4-octanolide
• CAS No.: 80041-01-6
• Molecular Formula: C9H16 O2
• Molecular Weight: 156.225
• UNII: 7A29T3GS95,29IPH2W8KP
• DSSTox Substance ID: DTXSID801017484
• Nikkaji Number: J181.415J
• Wikipedia: Trans-3-Methyl-4-octanolide
• Mol file: 80041-01-6.mol

Synonyms:Quercus lactone A;trans-Oaklactone;(3S,4R)-3-methyl-4-octanolide;trans-Whiskey lactone;Trans-3-Methyl-4-octanolide;(+-)-Quercus lactone;(+-)-Whiskey lactone;Whiskey lactone, (E)-;(+-)-trans-Whisky lactone;(+-)-trans-Quercus lactone;(+-)-trans-Whiskey lactone;UNII-7A29T3GS95;(+/-)-trans-Whiskey lactone;FEMA No. 3803, trans-;7A29T3GS95;80041-01-6;UNII-29IPH2W8KP;FEMA No. 3803, trans-(+-)-;29IPH2W8KP;2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4S,5R)-;39638-67-0;trans-beta-Methyl-gamma-octalactone;5-Butyl-4-methyldihydro-2(3H)-furanone, trans-;2(3H)-Furanone, 5-butyldihydro-4-methyl-, trans-;2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4S-trans)-;2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5S)-rel-;trans-4-Hydroxy-3-methyloctanoic acid gamma-lactone;5-Butyl-4-methyldihydro-2(3H)-furanone, trans-(+-)-;(+)-Oaklactone;(E)-Whiskeylactone;trans-Wiskey lactone;(+)-QUERCUS LACTONE;(+)-WHISKEY LACTONE;SCHEMBL7178100;(+)-TRANS-WHISKY LACTONE;DTXSID801017484;(+)-TRANS-QUERCUS LACTONE;(+)-TRANS-WHISKEY LACTONE;(3S, 4R)-3-methyl-4-octanolide;(4S,5R)-5-butyl-4-methyloxolan-2-one;FEMA NO. 3803, TRANS-(+)-;(trans)-3-methyloctanoic acid-gamma-lactone;TRANS-.BETA.-METHYL-.GAMMA.-OCTALACTONE;.BETA.-METHYL-.GAMMA.-OCTALACTONE, TRANS-;.BETA.-METHYL-.GAMMA.-OCTALACTONE, TRANS-(3S,4R)-;5-BUTYL-4-METHYLDIHYDRO-2(3H)-FURANONE, TRANS-(+)-;TRANS-4-HYDROXY-3-METHYLOCTANOIC ACID .GAMMA.-LACTONE

Chemical Property of Trans-3-Methyl-4-octanolide

Chemical Property:

• PSA: 26.30000
• 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%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1C(CC(=O)O1)C
• Isomeric SMILES: CCCC[C@@H]1[C@H](CC(=O)O1)C

Technology Process of Trans-3-Methyl-4-octanolide

There total 102 articles about Trans-3-Methyl-4-octanolide 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:

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

cis-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone

n-butyl magnesium bromide

3-formyl-butyric acid methyl ester

Downstream raw materials:

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

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

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

i‐propyl‐4‐hydroxy‐3‐methyloctanoate

Refernces

• 1、 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.
• 2、 Berree, Fabienne,Gernigon, Nicolas,Hercouet, Alain,Chia, Hui Lin,Carboni, Bertrand. "SN2′ boron-mediated Mitsunobu reactions - A new one-pot three-component synthesis of substituted enamides and enol benzoates". supporting information; experimental part. p. 329 - 333. Retrieved 2009/07/04.