1,4-cineole

Structural formula
General
Surname	1,4-cineole
other names	1-isopropyl-4-methyl-7-oxabicyclo [2.2.1] heptane; Isocineol; 1,4-epoxy-p-menthane;
Molecular formula	C 10 H 18 O
Brief description	colorless liquid with a slight smell of camphor
External identifiers / databases
EC number	207-428-9
ECHA InfoCard	100.006.755
PubChem	10106
Wikidata	Q12470088
properties
Molar mass	154.25 g mol −1
Physical state	liquid
density	0.887 g cm −3 (25 ° C)
Melting point	−46 ° C
boiling point	65 ° C (16 mmHg); 173-174 ° C;
solubility	practically insoluble in water; soluble in oils and ethanol ;
Refractive index	1.445 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,4-Cineol is a chemical compound from the group of the bicyclic epoxy monoterpenes .

Occurrence

1,4-cineole occurs naturally in apricots , orange and grapefruit juice, lime oil, wine, cocoa , rosemary , cubeb pepper and other natural products.

apricot
Grapefruit
orange

Extraction and presentation

Structure of 1,8-cineole

1,4-Cineol can be obtained as a mixture with 1,8-Cineol by reacting isoprene with sulfuric acid at 30 ° C. It can also be represented by gradual reduction of ascaridol .

properties

1,4-Cineol is a colorless liquid with a slight smell of camphor , which is practically insoluble in water.

use

1,4-cineole is used as a flavoring agent.

Individual evidence

↑ ^a ^b ^c ^d George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9412-6 , pp. 590 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d ^e ^f ^g Data sheet 1,4-Cineol, ≥85% from Sigma-Aldrich , accessed on September 5, 2015 ( PDF ).
^ S. Huneck, Joachim Thiem: RÖMPP Lexikon Naturstoffe, 1st edition, 1997 . Georg Thieme Verlag, 2014, ISBN 3-13-179291-4 , p. 136 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2009, ISBN 978-1-4200-9086-4 , pp. 292 ( limited preview in Google Book search).
↑ John ApSimon: The Total Synthesis of Natural Products . John Wiley & Sons, 2009, ISBN 0-470-12951-4 , pp. 134 ( limited preview in Google Book search).
↑ Günther Ohloff: Fragrances and olfactory sense The molecular world of fragrances . Springer-Verlag, 2013, ISBN 978-3-662-09768-7 , pp. 223 ( limited preview in Google Book search).

[George_A._Burdock1-1] George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9412-6 , pp. 590 ( limited preview in Google Book search).

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g Data sheet 1,4-Cineol, ≥85% from Sigma-Aldrich , accessed on September 5, 2015 ( PDF ).

[S._Huneck,_Joachim_Thiem-3] S. Huneck, Joachim Thiem: RÖMPP Lexikon Naturstoffe, 1st edition, 1997 . Georg Thieme Verlag, 2014, ISBN 3-13-179291-4 , p. 136 ( limited preview in Google Book search).

[George_A._Burdock-4] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2009, ISBN 978-1-4200-9086-4 , pp. 292 ( limited preview in Google Book search).

[John_ApSimon-5] John ApSimon: The Total Synthesis of Natural Products . John Wiley & Sons, 2009, ISBN 0-470-12951-4 , pp. 134 ( limited preview in Google Book search).

[Günther_Ohloff-6] Günther Ohloff: Fragrances and olfactory sense The molecular world of fragrances . Springer-Verlag, 2013, ISBN 978-3-662-09768-7 , pp. 223 ( limited preview in Google Book search).