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

Names

[ CAS No. ]:
470-67-7

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

[Synonym ]:
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane
Isocineole
1,4-Cineole (natural)
MFCD00209502
1-isopropyl-4-methyl-7-oxa-bicyclo[2.2.1]heptane
1-(2-methylethyl)-4-methyl-7-oxabicyclo[2.2.1]heptane
1,4-EPOXY-P-MENTHANE
1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
7-Oxabicyclo[2.2.1]heptane, 1-methyl-4-(1-methylethyl)-
1,4-Cineol
1,4-Cineole
FEMA No. 3658
p-Menthane,1,4-epoxy
EINECS 207-428-9
p-Menthane, 1,4-epoxy

Biological Activity

[Description]:

1,4-Cineole is a widely distributed, natural, oxygenated monoterpene[1]. 1,4-Cineole, present in eucalyptus oil, activates both human TRPM8 and human TRPA1[2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[References]

[1]. Rosazza JP, et al. Microbial hydroxylation of 1,4-cineole. Appl Environ Microbiol. 1987 Oct;53(10):2482-6.

[2]. Takaishi M, et al. 1,8-cineole, a TRPM8 agonist, is a novel natural antagonist of human TRPA1. Mol Pain. 2012 Nov 29;8:86.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
173.5±8.0 °C at 760 mmHg

[ Melting Point ]:
−46 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₈O

[ Molecular Weight ]:
154.249

[ Flash Point ]:
50.7±15.3 °C

[ Exact Mass ]:
154.135757

[ PSA ]:
9.23000

[ LogP ]:
2.58

[ Vapour Pressure ]:
1.7±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.491

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OS9274000

CHEMICAL NAME :: p-Menthane, 1,4-epoxy-

CAS REGISTRY NUMBER :: 470-67-7

BEILSTEIN REFERENCE NO. :: 0104974

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C10-H18-O

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 26,291,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 26,291,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2327 No. of Facilities: 2350 (estimated) No. of Industries: 29 No. of Occupations: 26 No. of Employees: 38044 (estimated) No. of Female Employees: 9165 (estimated)

Safety Information

[ Symbol ]:

GHS02

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H226

[ Precautionary Statements ]:
P210-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Risk Phrases ]:
R10

[ Safety Phrases ]:
S16

[ RIDADR ]:
UN 1993 3/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
OS9274000

[ Packaging Group ]:
III

[ Hazard Class ]:
3.2

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Inhibition by menthol and its related chemicals of compound action potentials in frog sciatic nerves.

Life Sci. 92(6-7) , 359-67, (2013)

Transient receptor potential (TRP) vanilloid-1 (TRPV1) and melastatin-8 (TRPM8) channels play a role in transmitting sensory information in primary-afferent neurons. TRPV1 agonists at high concentrati...

1,8-cineole, a TRPM8 agonist, is a novel natural antagonist of human TRPA1.

Mol. Pain 8 , 86, (2012)

Essential oils are often used in alternative medicine as analgesic and anti-inflammatory remedies. However, the specific compounds that confer the effects of essential oils and the molecular mechanism...

[Analysis of the chemical constituents of essential oil from Chimonanthus zhejiangensis by GC-MS].

Zhong Yao Cai 33(3) , 385-7, (2010)

To analyze the chemical constituents of the essential oil from Chimonanthus zhejiangensis.Steam distillation was employed to extract volatile compounds of essential oil from Chimonanthus zhejiangensis...