Cyclamen aldehyde

Last updated
Cyclamen aldehyde
Cyclamen aldehyde.svg
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.874 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-161-7
PubChem CID
UNII
  • 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
  • CC(C)c1ccc(cc1)CC(C)C=O
Properties
C13H18O
Molar mass 190.286 g·mol−1
AppearanceColorless liquid
Odor Strong floral aroma
Density 0.95 g/mL
Boiling point 270 °C (518 °F; 543 K)
Insoluble
Solubility in other solventsSoluble 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).

Cyclamen aldehyde is an organic compound with the formula (CH3)2CHC6H4CH2CH(CH3)CHO. It is a chiral compound although it is most commonly used as the racemate. It is a component of fragrances. [1] It has been used in soaps, detergents, lotions, and perfumes since the 1920s. [2] It was granted generally recognized as safe (GRAS) status by the 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. It is a colorless compound, although commercial samples can appear yellowish.. [1]

Synthesis

Cyclamen aldehyde is not naturally occurring and is prepared by the crossed-aldol condensation of cuminaldehyde and propionaldehyde followed by catalytic hydrogenation. [3] Other routes have been reported.. [1]

References

  1. 1 2 3 Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN   978-3-527-30673-2.
  2. ↑ "Monographs on fragrance raw materials". Food and Cosmetics Toxicology. 12 (3): 397. June 1974. doi:10.1016/0015-6264(74)90018-2.
  3. ↑ Bedoukian, Paul Z. (1967). Perfumery and Flavoring Synthetics (2nd ed.). Elsevier Publishing Co. p. 145.
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