Chemical Properties
clear colorless to yellow liquid
Chemical Properties
Cuminaldehyde has a strong, pungent, cumin-like odor and similar taste.
Occurrence
Reported in a large number of essential oils, cumin, Acacia farnesiana, cinnamon, bitter orange, Mexican
lime, Eucalyptus globulus, rue, boldus, Artemisia hausiliensis and others. Also reported in lemon and mandarin peel oil, cinnamon
bark, anise, clove bud, cumin seed, turmeric, parsley, calabash nutmeg (Monodora myristica Dunal), angelica root, thyme, beef,
brandy, grape and mastic gum fruit oil.
Definition
ChEBI: A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.
Preparation
From p-isopropylbenzyl chloride and hexamethylenetetramine (Arctander, 1969).
Taste threshold values
Taste characteristics at 10 ppm: spicy with green cumin and herbal nuances.
General Description
Cuminaldehyde is a constituent of cumin oil that exhibits strong antifungal and antibacterial activities.
Biochem/physiol Actions
Cuminaldehyde increases the insulin secretion in streptozotocin-induced diabetic rats. It suppresses melanin formation in cultured murine B16-F10 melanoma cells.
Synthesis
Prepared synthetically by heating p-isopropyl benzoyl chloride with an aqueous or alcoholic hexamethylenetetraamine solution.
Purification Methods
A likely impurity is the benzoic acid. Check the IR for the presence of OH from CO2H, and the CO frequencies. If the acid is present, then dissolve the aldehyde in Et2O, wash it with 10% NaHCO3 until effervescence ceases, then with brine, dry over CaCl2, evaporate and distil the residual oil, preferably under vacuum. It is almost insoluble in H2O, but soluble in EtOH and Et2O. The thiosemicarbazone has m 147o after recrystallisation from aqueous EtOH, MeOH or *C6H6. [Crounse J Am Chem Soc 71 1263 1949, Bernstein et al. J Am Chem Soc 73 906 1951, Gensler & Berman J Am Chem Soc 80 4949 1958, Beilstein 7 H 318, 7 II 347, 7 III 1095, 7 IV 723.]
