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27395

Sigma-Aldrich

1,4-Cineole

technical, mixture of isomers, ≥85% (GC)

Synonym(s):

1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
470-67-7
Molecular Weight:
154.25
Beilstein:
104974
EC Number:
207-428-9
MDL number:
MFCD00209502
UNSPSC Code:
12352100
PubChem Substance ID:
57648243
NACRES:
NA.22

grade

technical

Assay

≥85% (GC)

form

liquid

composition

1,4-cineol, ~75%
1,8-cineol, ~15%

refractive index

n20/D 1.445 (lit.)
n20/D 1.447

bp

65 °C/16 mmHg (lit.)

mp

−46 °C (lit.)

density

0.887 g/mL at 25 °C (lit.)

SMILES string

CC(C)C12CCC(C)(CC1)O2

InChI

1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3/t9-,10+

InChI key

RFFOTVCVTJUTAD-AOOOYVTPSA-N

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General description

1,4-Cineole is present in eucalyptus oil. It activated both human TRPA1 (a sensor of noxious cold) and human TRPM 8 (a thermosensitive receptor). It is a natural monoterpene that inhibits plant growth.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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W Liu et al.
Applied and environmental microbiology, 59(11), 3889-3893 (1993-11-01)
A cytochrome P-450-dependent monooxygenase system that catalyzes the stereospecific hydroxylation of the monoterpene substrate 1,4-cineole was demonstrated in cell-free preparations of Bacillus cereus UI-1477. 1,4-Cineole hydroxylations were catalyzed by a 100,000 x g (1-h)-centrifuging soluble, hexane-inducible enzyme that activated and
L Ji et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 22(8), 489-492 (1997-08-01)
The essential oils from the dried stems of Ephedra sinica, E. intermedia and E. equisetina were analyzed by GC-MS qualitatively and GC quantitatively. One hundred and twenty-seven constituents were identified, l-alpha-terpineol (31.64%) in E. sinica, 1,4-cineole (12.80%) in E. intermedia
M Miyazawa et al.
Xenobiotica; the fate of foreign compounds in biological systems, 31(10), 713-723 (2001-11-07)
1. Oxidation of 1,4-cineole, a monoterpene cyclic ether, was studied in rat and human liver microsomes and recombinant cytochrome P450 (P450 or CYP) enzymes expressed in insect cells in which human P450 and NADPH-P450 reductase cDNAs have been introduced. On
Patrícia Bezerra Gomes et al.
Pharmacology, biochemistry, and behavior, 96(3), 287-293 (2010-07-31)
Recent studies have shown that some monoterpenes exert anxiolytic- and depressant-like actions, however, these effects from monoterpene 1,4-cineole are still unknown. This work aimed to study the effects of 1,4-cineole in classic animal models for depression- and anxiety-like behavior, specifically
Y Asakawa et al.
Xenobiotica; the fate of foreign compounds in biological systems, 18(10), 1129-1134 (1988-10-01)
1. The metabolism of 1,4-cineole, a monoterpene ether, was studied in the rabbit. 2. Four neutral and one acidic metabolites were isolated from the urine and shown to be 9-hydroxy-1,4-cineole, 3,8-dihydroxy-1,4-cineole, 8,9-dihydroxy-1,4-cineole, 1,4-cineole-8-en-9-ol and 1,4-cineole-9-carboxylic acid.
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