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Sigma-Aldrich

(+)-Limonene oxide, mixture of cis and trans

97%

Synonym(s):

(3R)-6-Methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane, (4R)-1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, (4R)-Limonene 1,2-epoxide

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
203719-54-4
Molecular Weight:
152.23
MDL number:
MFCD00074770
UNSPSC Code:
12352005
PubChem Substance ID:
24853059
NACRES:
NA.22

Assay

97%

form

liquid

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.466 (lit.)

bp

113-114 °C/50 mmHg (lit.)

density

0.929 g/mL at 25 °C (lit.)

SMILES string

CC(=C)[C@@H]1CCC2(C)OC2C1

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?/m1/s1

InChI key

CCEFMUBVSUDRLG-XNWIYYODSA-N

General description

Limonene oxide, also known as limonene 1,2-epoxide, is a monoterpene that can be prepared from limonene. It has antinociceptive and antitumoral activities and is used in many products like food additives, cosmetics, and perfumes.

Application

(+)-Limonene oxide (mixture of cis and trans) undergoes biocatalytic resolution in the presence of epoxide hydrolase to form enantiomerically pure cis- and trans-limonene oxides.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

149.0 °F - closed cup

Flash Point(C)

65 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Efficient Epoxide Hydrolase Catalyzed Resolutions of (+)-and (-)-cis/trans-Limonene Oxides.
Ferrandi EE, et al.
ChemCatChem, 7(19), 3171-3178 (2015)
Antonia Amanda C de Almeida et al.
Brain research, 1448, 56-62 (2012-03-01)
The aim of the study is to determine the acute toxicity and anxiolytic-like effects of a mixture of cis and trans of (+)-limonene epoxide in animal models of anxiety. After acute treatment with (+)-limonene epoxide at doses of 25, 50
Kelli L Hvorecny et al.
Structure (London, England : 1993), 25(5), 697-707 (2017-04-11)
Pseudomonas aeruginosa secretes an epoxide hydrolase with catalytic activity that triggers degradation of the cystic fibrosis transmembrane conductance regulator (CFTR) and perturbs other host defense networks. Targets of this CFTR inhibitory factor (Cif) are largely unknown, but include an epoxy-fatty

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