3-octanol

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	3-octanol
other names	Ethyl pentyl carbinol; n -amylethyl carbinol; 3-OCTANOL ( INCI ) ;
Molecular formula	C 8 H 18 O
Brief description	colorless liquid with an aromatic odor
External identifiers / databases
EC number	209-667-4
ECHA InfoCard	100.008.790
PubChem	11527
ChemSpider	11043
Wikidata	Q27154917
properties
Molar mass	130.23 g mol −1
Physical state	liquid
density	0.82 g cm −3
Melting point	−45 ° C
boiling point	173 ° C; 174-176 ° C [( S ) - (+) - 3-octanol];
solubility	practically insoluble in water; soluble in ethanol and many oils;
Refractive index	1.426 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319
	P: 261-305 + 351 + 338
Toxicological data	> 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ; > 5000 mg kg −1 ( LD 50 , rat , oral ) ;
	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

3-Octanol is a chemical compound from the group of alcohols , more precisely the chiral alcohols.

Occurrence

Basil ( Ocimum basilicum )

3-Octanol occurs naturally in spearmint oil , oat groats , basil , allspice leaves , and truffles . The compound has been detected (free and esterified) in a variety of mints , lavender , the essential oils of field mint and spearmint , in apples, bananas, cranberries , grapes, papaya , strawberries , sour cherries , lemons , blackberries , pork, peas , potatoes , Ginger , thyme , fish, fried beef, cognac , rum , wine , coffee , tea , oats , soybeans , mushrooms, marjoram , seaweed , buckwheat , lemon balm , truffles, passion fruit and pepino fruit (Solanum muricatum).

It serves as an alarm pheromone for some ants . The mandible glands of the ant species Myrmica contain 3-octanol, 90% of it in the form of the ( R ) - enantiomer , among other substances . The species M. rubra and scabrinodis react specifically to this ( R ) -isomer.

3-Octanol can be produced in racemic form by reducing 3-octanone with sodium in an ether solution.

3-Octanol is a flammable, hardly inflammable, colorless liquid with an aromatic odor that is practically insoluble in water.

3-Octanol is used as a flavoring agent (e.g. for lavender and mushroom smells).

The vapors of 3-octanol can form an explosive mixture with air ( flash point 68 ° C).

↑ Entry on 3-OCTANOL in the CosIng database of the EU Commission, accessed on January 21, 2020.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 3-octanol in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .
↑ ^a ^b Data sheet (S) - (+) - 3-octanol, 97% from Sigma-Aldrich , accessed on April 23, 2017 ( PDF ).
↑ ^a ^b ^c ^d George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 1526 ( limited preview in Google Book search).
↑ ^a ^b Data sheet 3-Octanol, natural, ≥97%, FCC, FG from Sigma-Aldrich , accessed on April 23, 2017 ( PDF ).
↑ John L. Capinera: Encyclopedia of Entomology . Springer Science & Business Media, 2008, ISBN 978-1-4020-6242-1 , p. 92 ( limited preview in Google Book search).
↑ MC. CAMMAERTS, K. MORI: Behavioral activity of pure chiral 3-octanol for the ants Myrmica scabrinodis Nyl. and Myrmica rubra L. In: Physiological Entomology. 12, 1987, p. 381, doi: 10.1111 / j.1365-3032.1987.tb00764.x .
^ Wiley-VCH: Ullmann's Food and Feed, 3 Volume Set . John Wiley & Sons, 2017, ISBN 978-3-527-33990-7 , pp. 1059 ( limited preview in Google Book search).