α-isomethylionone

Structural formula
General
Surname	Α-isomethylionone
other names	α-cetone; α-isomethyl ionone; 3-methyl-4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one; Isomethyl-α-ionone;
Molecular formula	C 14 H 22 O
Brief description	light yellow liquid with a floral odor
External identifiers / databases
EC number	204-846-3
ECHA InfoCard	100.004.407
PubChem	5372174
ChemSpider	4522510
Wikidata	Q2204200
properties
Molar mass	206.32 g mol −1
Physical state	liquid
density	0.93 g cm −3 (20 ° C)
boiling point	93 ° C (3.1 mmHg)
Refractive index	1.5000-1.5020 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 317-412
	P: 273-280
	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

α-Isomethylionon is a chemical compound from the group of cycloalkenes . The compound is one of the isomers of methylionone .

Extraction and presentation

α-Isomethylionone can be produced by a crossed aldol condensation of citral with methyl ethyl ketone , with the 7,11- as an intermediate stage with the desired methyl pseudoionone (3,6,10-trimethyl-3,5,9-undecatrien-2-one) as a by-product Dimethyl-4,6,10-dodecatrien-3-one is formed. The methyl pseudoionone is then cyclized to a mixture of α- and β-isomethylionone using a strong alkali compound and high temperature .

properties

α-Isomethylionone is a light yellow liquid with a floral odor.

use

α-Isomethylionone is a fragrance that is often added to deodorants and perfumes. It is one of the allergens that are responsible for axillary dermatitis . The compound is used for studies on contact sensitization to identify allergens in cosmetic preparations.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g data sheet α-Isomethylionone, odorant used in allergy studies at Sigma-Aldrich , accessed on December 8, 2018 ( PDF ).
↑ ^a ^b Wolfgang Legrum: Fragrances, between stench and fragrance Occurrence, properties and use of fragrances and their mixtures . Springer-Verlag, 2011, ISBN 978-3-8348-8276-9 , pp. 143 ( limited preview in Google Book search).
↑ ^a ^b ^c George A. Burdock: Encyclopedia of Food & Color Additives . CRC Press, 2014, ISBN 978-1-4987-1108-1 , pp. 1476 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet α-Isomethylionone, odorant used in allergy studies at Sigma-Aldrich , accessed on December 8, 2018 ( PDF ).

[Wolfgang_Legrum-2] Wolfgang Legrum: Fragrances, between stench and fragrance Occurrence, properties and use of fragrances and their mixtures . Springer-Verlag, 2011, ISBN 978-3-8348-8276-9 , pp. 143 ( limited preview in Google Book search).

[George_A._Burdock-3] George A. Burdock: Encyclopedia of Food & Color Additives . CRC Press, 2014, ISBN 978-1-4987-1108-1 , pp. 1476 ( limited preview in Google Book search).