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Cuminaldehyde

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Cuminaldehyde Basic information

Product Name:
Cuminaldehyde
CAS:
122-03-2
MF:
C10H12O
MW:
148.2
EINECS:
204-516-9
Mol File:
122-03-2.mol
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Cuminaldehyde Chemical Properties

Boiling point:
235-236 °C(lit.)
Density 
0.977 g/mL at 25 °C(lit.)
FEMA 
2341 | CUMINALDEHYDE
refractive index 
n20/D 1.529(lit.)
Flash point:
200 °F
storage temp. 
Store below +30°C.
solubility 
ethanol: soluble1mL/4ML, clear, colorless (70%)
form 
Liquid
color 
Clear colorless to yellow
Water Solubility 
insoluble
Sensitive 
Air Sensitive
JECFA Number
868
Merck 
14,2621
BRN 
636547
CAS DataBase Reference
122-03-2(CAS DataBase Reference)
NIST Chemistry Reference
Benzaldehyde, 4-(1-methylethyl)-(122-03-2)
EPA Substance Registry System
Cuminaldehyde (122-03-2)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
2
RTECS 
CU7000000
TSCA 
Yes
HS Code 
29122900
Toxicity
LD50 orally in rats: 1390 mg/kg (Jenner)

MSDS

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Cuminaldehyde Usage And Synthesis

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.

Uses

Cuminaldehyde is a flavoring agent that is a liquid, colorless to yellow in appearance, with a strong pungent odor resembling cumin oil. It is insoluble in water and soluble in alcohol and ether. It is obtained from cumin oil. It is also termed p-, cumaldehyde, and cuminal.

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.

Safety Profile

Moderately toxic by ingestion and skin contact. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Chemical 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.]

Cuminaldehyde Preparation Products And Raw materials

Preparation Products

Raw materials

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