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1,4-Cineole

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1,4-Cineole Basic information

Product Name:
1,4-Cineole
Synonyms:
  • FEMA 3658
  • ISOCINEOLE
  • CINEOLE, 1,4-
  • 1,4-cineol
  • 1,4-epoxy-p-menthan
  • 1,4-Epoxy-p-menthane
  • 1-isopropyl-4-methyl-7-oxabicyclo(2.2.1)heptan
  • 1-methyl-4-(1-methylethyl)-7-oxabicyclo(2.2.1)heptan
CAS:
470-67-7
MF:
C10H18O
MW:
154.25
EINECS:
207-428-9
Product Categories:
  • Miscellaneous Natural Products
Mol File:
470-67-7.mol
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1,4-Cineole Chemical Properties

Melting point:
-46 °C (lit.)
Boiling point:
65 °C/16 mmHg (lit.)
Density 
0.887 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.445(lit.)
FEMA 
3658 | 1,4-CINEOLE
Flash point:
118 °F
storage temp. 
Store at -20°C
Water Solubility 
Slightly soluble in water
solubility 
Almost insoluble in water, soluble in alcohol and oils. DMSO: 125 mg/mL (810.37 mM)
form 
Liquid
color 
Colorless to Almost colorless
Odor
Cool, somewhat spicy-herbaceous taste
Odor Type
herbal
JECFA Number
1233
BRN 
104974
LogP
2.97
CAS DataBase Reference
470-67-7(CAS DataBase Reference)
NIST Chemistry Reference
7-Oxabicyclo[2.2.1]heptane, 1-methyl-4-(1-methylethyl)-(470-67-7)
EPA Substance Registry System
1,4-Cineole (470-67-7)
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Safety Information

Risk Statements 
10
Safety Statements 
16
RIDADR 
UN 1993 3/PG 3
WGK Germany 
2
RTECS 
OS9274000
10
HS Code 
2932.19.5100
HazardClass 
3.2
PackingGroup 
III
Hazardous Substances Data
470-67-7(Hazardous Substances Data)

MSDS

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1,4-Cineole Usage And Synthesis

Chemical Properties

1,4-Cineole has a light and mild camphoraceous odor and a cool, mildly spice-like flavor.

Occurrence

Reported present in Piper cubeba, lime peel oil, apricot, cardamom (Eleteria cardamomun Maton), orange juice, grapefruit juice, laurel (Laurus nobilis L), rosemary and mastic gum leaf oil. It is also present in various essential oils; Boldea fragrans Juss., Xanthoxylum rhetsa D.C. and Ormenis multicaulis.

Uses

Apart from the academic interest related to the olfactory similarity or dissimilarity) of isomer chemicals, there is not much interest in this chemical. It is not nearly as readily available as its isomer, Eucalyptol.

Definition

ChEBI: 1,4-cineole is an oxabicycloalkane consisting of p-menthane with an epoxy bridge across positions 1 and 4. It has a role as a plant metabolite, a fumigant insecticide and a central nervous system depressant. It is a cineole and an oxabicycloalkane.

Taste threshold values

Taste characteristics at 40 ppm: cooling, minty, menthol-like, green and herbal, with a terpy and camphoraceous nuance.

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.

Synthesis

Its structure has been confirmed through synthesis.*

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