Cuminaldehyde

Structural formula
General
Surname	Cuminaldehyde
other names	4-isopropylbenzaldehyde; p -isopropylbenzaldehyde; Cuminal;
Molecular formula	C 10 H 12 O
External identifiers / databases
EC number	204-516-9
ECHA InfoCard	100.004.107
PubChem	326
Wikidata	Q419952
properties
Molar mass	148.20 g mol −1
Physical state	liquid
density	0.977 g cm −3 (25 ° C)
boiling point	235-236 ° C
Refractive index	1.529 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
	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

Cumaldehyde ( 4-isopropylbenzaldehyde ) is structurally derived from benzaldehyde or cumene (isopropylbenzene) and belongs to the large group of terpenes .

Occurrence

The caraway seeds are rich in essential oils

It is a component of essential oils from eucalyptus , myrrh , cassia , caraway and other types. It has a pleasant odor and is used commercially in perfumes and other cosmetics.

Manufacturing

Cuminaldehyde may be synthetically prepared by the reduction of 4-isopropylbenzoyl chloride, or by formylation of cumene can be produced.

properties

Cumaldehyde is the biologically active component of the seed oil of cumin ( Cuminum cyminum ). The substances obtained from these seeds have an in vitro inhibiting effect on aldose reductase and alpha-glucosidase in rats . This inhibitory effect suggests a potential use as an antidiabetic agent. The terpenoid cuminaldehyde mostly undergoes reduction but not oxidation during biotransformation in mammals. It is one of the volatile compounds of the cumin aroma and can be detected in traces in the blood and milk of sheep whose feed and the like. a. Cumin seeds were added.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet cuminaldehyde from Sigma-Aldrich , accessed on November 8, 2016 ( PDF ).
↑ HS Lee: "Cuminaldehyde: Aldose Reductase and alpha-glucosidase Inhibitor Derived from Cuminum cyminum L. Seeds", in: J. Agric. Food Chem. , 2005 Apr 6, 53 (7), pp. 2446-5240; PMID 15796577 .
↑ T. Ishida, M. Toyota, Y. Asakawa: “Terpenoid biotransformation in mammals. V. Metabolism of (+) - citronellal, (±) -7-hydroxycitronellal, citral, (-) - perillaldehyde, (-) - myrtenal, cuminaldehyde, thujone, and (±) -carvone in rabbits ", in: Xenobiotica , 1989 Aug, 19 (8), pp. 843-855; PMID 2815827 .
↑ M. Désage, B. Schaal, J. Soubeyrand, P. Orgeur, JL Brazier: "Gas chromatographic-mass spectrometric method to characterize the transfer of dietary odorous compounds into plasma and milk", in: J. Chromatogr. B , Biomed Appl. , 1996 Apr 12, 678 (2), pp. 205-210; PMID 8738023 .

literature

Alfred Raab: "Mittheilungen: About some derivatives of cuminaldehyde", in: Reports of the German Chemical Society , 1875 , 8 (2), pp. 1148-1152; doi : 10.1002 / cber.18750080273 .

Web links

Entry for cuminaldehyde in the Human Metabolome Database (HMDB) , accessed September 24, 2013.

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet cuminaldehyde from Sigma-Aldrich , accessed on November 8, 2016 ( PDF ).

[2] HS Lee: "Cuminaldehyde: Aldose Reductase and alpha-glucosidase Inhibitor Derived from Cuminum cyminum L. Seeds", in: J. Agric. Food Chem. , 2005 Apr 6, 53 (7), pp. 2446-5240; PMID 15796577 .

[3] T. Ishida, M. Toyota, Y. Asakawa: “Terpenoid biotransformation in mammals. V. Metabolism of (+) - citronellal, (±) -7-hydroxycitronellal, citral, (-) - perillaldehyde, (-) - myrtenal, cuminaldehyde, thujone, and (±) -carvone in rabbits ", in: Xenobiotica , 1989 Aug, 19 (8), pp. 843-855; PMID 2815827 .

[4] M. Désage, B. Schaal, J. Soubeyrand, P. Orgeur, JL Brazier: "Gas chromatographic-mass spectrometric method to characterize the transfer of dietary odorous compounds into plasma and milk", in: J. Chromatogr. B , Biomed Appl. , 1996 Apr 12, 678 (2), pp. 205-210; PMID 8738023 .