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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

Quality Level

100

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.)

functional group

ether

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF7053
BCCD3699
BCCC6484
BCCB1629
BCCB1628

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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
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.
Abdul Ahad et al.
Current drug delivery, 8(2), 213-224 (2011-01-18)
The purpose of this study was to investigate the effectiveness and mechanism(s) of percutaneous absorption of propranolol hydrochloride (PHCL) across rat and human cadaver skin using seven novel terpenes with reference to marker terpene 1,8-cineole. In-vitro skin permeation studies were
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
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
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