Cuminaldehyde Property

Melting point:

97 °C

Boiling point:

235-236 °C(lit.)

Density 

0.977 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.529(lit.)

FEMA 

2341 | CUMINALDEHYDE

Flash point:

200 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

ethanol: soluble1mL/4ML, clear, colorless (70%)

form 

Liquid

color 

Clear colorless to yellow

Odor

at 10.00 % in dipropylene glycol. spicy cumin green herbal

Odor Type

spicy

Water Solubility 

insoluble

Sensitive 

Air Sensitive

JECFA Number

868

Merck 

14,2621

BRN 

636547

Dielectric constant

11.0（15℃）

LogP

3.17

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)

Safety

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

Cuminaldehyde Chemical Properties,Usage,Production

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.

Uses

Cuminaldehyde has been used to study larvicidal and adulticidal toxicity of monoterpenes against Culex pipiens. It has been used in evaluation of chemical composition, antimicrobial and antioxidant activities of essential oil and various extracts of Eucalyptus gilii.

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.

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.

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.]