906263
cis-(+)-Limonene oxide
Synonym(s):
(+)-cis-Limonene-1,2-epoxide, (1R,4R,6S)-1-methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, cis-(+)-1,2-Epoxy-p-menth-8-ene
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About This Item
Empirical Formula (Hill Notation):
C10H16O
CAS Number:
Molecular Weight:
152.23
MDL number:
UNSPSC Code:
12352212
NACRES:
NA.22
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form
liquid
density
0.932 g/mL
SMILES string
O1[C@@]2([C@H]1C[C@H](CC2)C(=C)C)C
InChI
1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9+,10-/m0/s1
InChI key
CCEFMUBVSUDRLG-AEJSXWLSSA-N
Related Categories
1 of 4
This Item | 906271 | 921459 | 8.18407 |
|---|---|---|---|
| form liquid | form liquid | form liquid | form liquid |
| density 0.932 g/mL | density 0.913 g/mL | density - | density 0.84 g/cm3 at 20 °C |
Application
cis-(+)-Limonene oxide can be used as:
- A monomer to prepare poly(limonene)carbonate by Al(III) catalyzed coupling reaction with CO2.[1]
- A reactant to prepare trans-diaxial diol via diastereoselective ring-opening reaction using molybdenum complex catalyst.[2]
- A reactant to synthesize trans-dihydrocarvone via isomerization reaction in the presence of silica-supported tungstophosphoric acid as a catalyst and dialkylcarbonate as a green solvent.[3]
cis-(+)-Limonene oxide is a valuable chiral terpene oxide building block.
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
160.7 °F
flash_point_c
71.5 °C
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Leticia Peña Carrodeguas et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(16), 6115-6122 (2015-03-05)
Amino-triphenolate derived Al(III) complexes combined with suitable nucleophiles have been investigated as binary catalysts for the coupling of limonene oxide and carbon dioxide to afford alternating polycarbonates. These catalysts are able to produce stereoregular, perfectly alternating trans-polymers from cis-limonene oxide
Heteropoly acid catalysis for the isomerization of biomass-derived limonene oxide and kinetic separation of the trans-isomer in green solvents
Cotta RF, et al.
Applied Catalysis A: General, 584, 117173-117173 (2019)
Diastereoselective ring opening of limonene oxide with water catalysed by β-ketophosphonate complexes of molybdenum(VI)
Salles L,et al.
Tetrahedron Asymmetry, 10(8), 1471-1476 (1999)
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