Pseudo-jonon

Structural formula
General
Surname	Pseudo-jonon
other names	Pseudoionon; ψ-Jonon; ψ-ionone; (3 E , 5 E ) -6,10-dimethyl-3,5,9-undecatrien-2-one;
Molecular formula	C 13 H 20 O
Brief description	yellowish oil
External identifiers / databases
EC number	205-457-1
ECHA InfoCard	100,004,962
Wikidata	Q2115736
properties
Molar mass	192.30 g mol −1
Physical state	liquid
density	0.8951 g cm −3 (20 ° C)
Melting point	−75 ° C
boiling point	265.4 ° C
Vapor pressure	0.1741 Pa (20 ° C)
solubility	97 mg / l in water ; ; soluble in ethanol and diethyl ether ;
Refractive index	1.5335 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 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

Pseudoionone is one of the terpenes scoring chemical compound . It is available as a yellowish oil.

Occurrence

Pseudojonon is a compound found in nature. It was found in tobacco plants . When digesting lycopene (e.g. from tomatoes), humans form pseudojonon. In plants, it is an intermediate in the biosynthesis of lycopene. Pseudojonon could therefore be found in many flowering plants and therefore widespread in nature.

Extraction and presentation

Since pseudojonon only occurs in small amounts in nature, it is almost exclusively produced synthetically.

For example, citral is condensed with acetone in an alkaline medium for representation .

Technically today, pseudojonone is usually produced from acetoacetic ester and dehydrolinalool by heating to 160 ° C. A mixture of two different diastereomers falls here .

A considerable part (up to 40%) of the intermediate product also cyclizes here . However, this can be prevented by adapting the reaction conditions.

Pseudojonon is one of the chemical substances that are produced in large quantities (" High Production Volume Chemical ", HPVC) and for which the Organization for Economic Cooperation and Development (OECD) collects data on possible hazards (" Screening Information Dataset ", SIDS ) was made.

properties

Chemical properties

In acidic solution, pseudo -jonone cyclizes to α- and β-ionone . When using phosphoric acid mainly α-ionone is formed; with sulfuric acid mainly β-ionone is formed.

use

Pseudo-jonon is mainly used for the synthesis of α- and β-ionone.

Biological importance

Due to its similar structure to juvenile hormone III, pseudojonone acts as a juvenile hormone in insects . These control the formation of the larval characteristics or determine the goal of the moult.

Juvenile hormone III

literature

Lexicon entry: pseudojonon . In: Chemicals Lexicon. Status: January 6, 2000 (accessed on September 20, 2006)
W. Walter, W. Francke, Textbook of Organic Chemistry , 23rd edition, 1998, S. Hirzel Verlag Stuttgart - Leipzig

Individual evidence

↑ ^a ^b ^c Entry on pseudo-jonon. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for 3,5,9-undecatrien-2-one, 6,10-dimethyl- , accessed on October 3, 2014.
↑ ^a ^b Data sheet Pseudoionone, technical, mixture of isomers, ≥90% (GC) from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).

[roempp-1] Entry on pseudo-jonon. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.

[SIDS-2] ↑ ^a ^b ^c ^d ^e ^f ^g OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for 3,5,9-undecatrien-2-one, 6,10-dimethyl- , accessed on October 3, 2014.

[FLUKA-3] Data sheet Pseudoionone, technical, mixture of isomers, ≥90% (GC) from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).