Cyclamen aldehyde

Cyclamen aldehyde
Names
	IUPAC name 3-(4-Isopropylphenyl)-2-methylpropanal
	Other names Cyclamal; 2-Methyl-3-(p-isopropylphenyl)propionaldehyde; 3-(4-Isopropylphenyl)-2-methylpropanal; alpha-Methyl-p-isopropylcinnamaldehyde
Identifiers
CAS Number	103-95-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3183483;
ChemSpider	451801;
ECHA InfoCard	100.002.874
EC Number	203-161-7;
PubChem CID	517827;
UNII	4U37UX0E1E ;
CompTox Dashboard (EPA)	DTXSID2044769 ;
	InChI InChI=1S/C13H18O/c1-10(2)13-6-4-12(5-7-13)8-11(3)9-14/h4-7,9-11H,8H2,1-3H3 Key: ZFNVDHOSLNRHNN-UHFFFAOYSA-N;
	SMILES CC(C)c1ccc(cc1)CC(C)C=O;
Properties
Chemical formula	C13H18O
Molar mass	190.286 g·mol−1
Appearance	Colorless to pale yellow liquid
Odor	Strong floral aroma
Density	0.95 g/mL
Boiling point	270 °C (518 °F; 543 K)
Solubility in water	Insoluble
Solubility in other solvents	Soluble in most fixed oils, ethanol; Insoluble in propylene glycol, glycerin
Hazards
Flash point	109 °C (228 °F; 382 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Cyclamen aldehyde is a fragrance molecule which has been used in soaps, detergents, lotions, and perfumes since the 1920s.[1] It was granted generally recognized as safe (GRAS) status by Flavor and Extract Manufacturers Association (FEMA) in 1965 and is approved by the Food and Drug Administration for food use in the United States. The Council of Europe (1970) included cyclamen aldehyde in the list of admissible artificial flavoring substances, at a level of 1 ppm.

Synthesis

Cyclamen aldehyde is not naturally occurring and is prepared by the crossed-aldol condensation of cuminaldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst.[2]

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References

"Monographs on fragrance raw materials". Food and Cosmetics Toxicology. 12 (3): 397. June 1974. doi:10.1016/0015-6264(74)90018-2.
Bedoukian, P.Z. (1967). Pelfumery and Flavoring Synthetics (2nd ed.). Elsevier Publishing Co. p. 145.

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[1] "Monographs on fragrance raw materials". Food and Cosmetics Toxicology. 12 (3): 397. June 1974. doi:10.1016/0015-6264(74)90018-2.

[2] Bedoukian, P.Z. (1967). Pelfumery and Flavoring Synthetics (2nd ed.). Elsevier Publishing Co. p. 145.