Cyclamen aldehyde

Cyclamen aldehyde  File: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

CAS Number

* 103-95-7

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL3183483

ChemSpider |

* 451801

EC Number |

* 203-161-7

PubChem CID

* 517827

UNII |

* 4U37UX0E1E Y

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 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

Tracking categories (test):

* SizeSet

Cyclamen aldehyde is an organic compound with the formula (CH

2CHC

4CH
2CH(CH
3)CHO. It is a chiral compound although it is most commonly used as the racemate. It is a component of fragrances[1] described as "floral, cyclamen, fresh, rhubarb, musty, green".[2] It has been used in soaps, detergents, lotions, and perfumes since the 1920s.[3] 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.[4] Other routes have been reported..[1]

## References

1. ↑ 1.0 1.1 1.2 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. ↑ "cyclamen aldehyde". Scents and Flavors. https://scentsandflavors.com/database/9dbb4f65-bdb7-4492-aea4-18d89762c782.
3. ↑ "Monographs on fragrance raw materials". Food and Cosmetics Toxicology 12 (3): 397. June 1974. doi:10.1016/0015-6264(74)90018-2.
4. ↑ Bedoukian, Paul Z. (1967). Perfumery and Flavoring Synthetics (2nd ed.). Elsevier Publishing Co.. p. 145.

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*[CID]: Compound ID