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
ChemSpider	451801
Jmol interactive 3D	Image
UNII	4U37UX0E1E
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	190.29 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

It is not found in nature. It is prepared by the condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst.^[2]

References

1. "Monographs on fragrance raw materials" Check |url= value (help). Food and Cosmetics Toxicology 12: 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.