2'-Methoxycinnamaldehyde

Reported in EPA TSCA Inventory.

The o-Methoxy cinnamaldehyde with CAS registry number of 1504-74-1 is also known as 3-(2-Methoxyphenyl)acrylaldehyde. The IUPAC name is 3-(2-Methoxyphenyl)prop-2-enal. Its EINECS registry number is 216-131-3. In addition, the formula is C₁₀H₁₀O₂ and the molecular weight is 162.19. This chemical is a colorless crystal and should be sealed in cool and dry place. What's more, it is used as organic synthesis intermediate, and is also used for the production of spices, medicine.

Physical properties about o-Methoxy cinnamaldehyde are: (1)ACD/LogP: 2.13; (2)ACD/LogD (pH 5.5): 2.13; (3)ACD/LogD (pH 7.4): 2.13; (4)ACD/BCF (pH 5.5): 24.42; (5)ACD/BCF (pH 7.4): 24.42; (6)ACD/KOC (pH 5.5): 342.75; (7)ACD/KOC (pH 7.4): 342.75; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.559; (11)Molar Refractivity: 49 cm³; (12)Molar Volume: 151.7 cm³; (13)Surface Tension: 37.6 dyne/cm; (14)Density: 1.068 g/cm³; (15)Flash Point: 134.4 °C; (16)Enthalpy of Vaporization: 57.78 kJ/mol; (17)Boiling Point: 334.8 °C at 760 mmHg; (18)Vapour Pressure: 0.000125 mmHg at 25 °C.

Preparation of o-Methoxy cinnamaldehyde: it is prepared by methylation reaction of salicylaldehyde with dimethyl sulfate. Firstly, 30% sodium hydroxide solution is added to salicylaldehyde solution under stirring. The mixture is heated to boiling. Secondly, dimethyl sulfate is slowly added for 3 hours and the mixture is refluxed for another 2 or 3 hours. Then oil layer is cooled, washed with 5% sodium hydroxide solution and washed with water to pH 8. At last, product is obtained by drying and vacuum distillation. The yield is about 60%.

Uses of o-Methoxy cinnamaldehyde: it is used to produce 1-(3,3-diethoxy-propenyl)-2-methoxy-benzene by reaction with ethanol. The reaction occurs with catalyst I₂ for 1 hour. The yield is about 98%.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: COC1=CC=CC=C1C=CC=O
2. InChI: InChI=1S/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3
3. InChIKey: KKVZAVRSVHUSPL-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	> 2gm/kg (2000mg/kg)		Japanese Kokai Tokyo Koho Patents. Vol. #92-360829,
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 845, 1975.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 845, 1975.