Limonene oxide, (-)-

Base Information

• Chemical Name: Limonene oxide, (-)-
• CAS No.: 203719-53-3
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Nikkaji Number: J753.731J
• Wikidata: Q27155805
• Mol file: 203719-53-3.mol

Synonyms:Limonene oxide, (-)-;203719-53-3;(4S)-Limonene-1,2-epoxide;L-1,2-Epoxylimonene;L-Limonene 1,2-epoxide;(4S)-1-METHYL-4-(PROP-1-EN-2-YL)-7-OXABICYCLO[4.1.0]HEPTANE;UNII-19GI74JS93;FEMA No. 4656;L-8-p-Menthene-1,2-epoxide;7-OXABICYCLO[4.1.0]HEPTANE, 1-METHYL-4-(1-METHYLETHENYL)-, (4S)-;(4S)-1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo(4.1.0)heptane;(-)-limonene oxide;(4S)-Limonene oxide;a (4S)-limonene-1,2-epoxide;SCHEMBL15580358;CHEBI:82206;19GI74JS93;a (4S)-1,2-epoxymenth-8-ene;AKOS040752577;C19081;Q27155805;(4S)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane

Chemical Property of Limonene oxide, (-)-

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C(C1)O2)C
• Isomeric SMILES: CC(=C)[C@H]1CCC2(C(C1)O2)C

Technology Process of Limonene oxide, (-)-

There total 9 articles about Limonene oxide, (-)- 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: 75.0%

(-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (4S)-1-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]-heptane (96-08-2) + (-)-limonene oxide (203719-53-3)

Guidance literature:

With 1,1,1,3',3',3'-hexafluoro-propanol; urea-hydrogen peroxide; 1,1,1,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Icosafluoro-decan-2-one; at 25 ℃; for 0.75h;

DOI:10.1002/1099-0690(200210)2002:19<3290::AID-EJOC3290>3.0.CO;2-M

Reference yield: 45.0%

(-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (S)-4-Isopropenyl-1-methylcyclohexene 7,8-epoxide (213479-77-7) + (S)-1-Methyl-4-(2-methyl-oxiranyl)-7-oxa-bicyclo[4.1.0]heptane + (-)-limonene oxide (203719-53-3)

Guidance literature:

With Oxone; acetyl methyl β-cyclodextrin; sodium hydrogencarbonate; edetate disodium; In acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1021/jo034296d

Reference yield:

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (4R)-limonene 1,2-epoxide (1195-92-2) + (-)-limonene oxide (203719-53-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at 20 ℃; for 4h; Overall yield = 75 %;

DOI:10.1590/S0103-50532012005000005

upstream raw materials:

(-)-(S)-limonene

D-limonene

Downstream raw materials:

(3S)-4-methyl-3-(3-oxobutyl)pent-4-enal

(S)-p-mentha-6,8-dien-2-one

(2S,4S)-carveol

trans-2-methylene-5-isopropylenecyclohexanol

Refernces

• 1、 Ranganathan, Sumanth,Zeitlhofer, Sandra,Sieber, Volker. "Development of a lipase-mediated epoxidation process for monoterpenes in choline chloride-based deep eutectic solvents". . p. 2576 - 2586. Retrieved 2017.
• 2、 Vieira, Eduardo Guimar?es,Silva, Rafael Oliveira,Dal-Bó, Alexandre Gon?alves,Frizon, Tiago Elias Allievi,Filho, Newton Luiz Dias. "Syntheses and catalytic activities of new metallodendritic catalysts". . p. 9403 - 9414. Retrieved 2016/11/09.