Methyl cinnamate Chemical Properties

Melting point:

33-38 °C (lit.)

Boiling point:

260-262 °C (lit.)

Density 

1.092

vapor pressure 

0.73Pa at 25℃

refractive index 

1.5771

FEMA 

2698 | METHYL CINNAMATE

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly), soluble in alcohol, Propylene glycol, Mineral oil and oils.

form 

Fused Crystalline Mass

color 

White to light yellow

Specific Gravity

1.092

Odor

at 100.00 %. sweet balsam strawberry cherry cinnamon

Odor Type

balsamic

Water Solubility 

insoluble

JECFA Number

658

Merck 

14,2299

BRN 

386468

InChIKey

CCRCUPLGCSFEDV-BQYQJAHWSA-N

LogP

2.68 at 25℃

CAS DataBase Reference

103-26-4(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenoic acid, 3-phenyl-, methyl ester(103-26-4)

EPA Substance Registry System

Methyl cinnamate (103-26-4)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

1

RTECS 

GE0190000

TSCA 

Yes

HS Code 

29163990

Toxicity

Moderately toxic by ingestion . The oral LD₅₀ for rats is 2610 mg / kg . It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.

MSDS

• Language:English Provider:3-Phenyl-2-propenoic acid methyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl cinnamate Usage And Synthesis

Chemical Properties

Methyl cinnamate appears as white to slightly yellow crystals with a cherry and balsamic aroma. Melting point 34 ℃. The boiling point is 260°C, and the refractive index (nD20) is 1.5670. Relative density (d435) 1.0700. Soluble in alcohol, ether, glycerin, propylene glycol, most non-volatile oils and mineral oils, insoluble in water.
Natural products are contained in basil oil (up to 52%), galangal oil and bay leaf oil.

Preparative Methods

It is obtained by esterification of cinnamic acid with methanol. The mixture of cinnamic acid, methanol and sulfuric acid (or hydrochloric acid) was heated to reflux for 5 h, and the excess amount of methanol was added. Cool and spate the acid layer, washed with water and 10% sodium carbonate solution, and then washed with water to neutral. The crude product was subjected to recrystallization or vacuum distillation [collection of 132-134 ° C (2.0 kPa) fraction] to give methyl cinnamate with a yield of about 70%.

Description

Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98 %) with a 2 - 6 % fresh weight yield in the leaf and twigs.
Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry.
It is known to attract males of various orchid bees, such as Aglae caerulea.
Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida.

Chemical Properties

Methyl cinnamate has a fruity, balsamic odor similar to strawberry and a corresponding sweet taste.

Occurrence

Reported found in the oil from rhizomes of Alpinia malaccensis, in the oil from leaves of Ocimum canum Sims.; in the oil of Narcissus jonquilla L.; in the oil from rhizomes of Gastrochilus panduratum Ridl.; two isomers (cis- and trans-) exist in natural. Also reported found in cranberry, guava, pineapple, strawberry fruit and jam, cinnamon leaf, Camembert cheeses, cocoa, avocado, plum, prune, cloudberry, starfruit, plum brandy, rhubarb, beli (Aegle marmelos Correa), loquat and Bourbon vanilla.

Uses

Methyl cinnamate is used as a fragrance ingredient in cosmetics and household products.

Uses

Methyl cinnamate was used to inhibit monophenolase and diphenolase activity of mushroom tyrosinase and it also has antimicrobial ability. It is mainly is used in the flavor and perfume industries. It is known to attract males of various orchid bees, such as Aglae caerulea.

Definition

ChEBI: Methyl cinnamate is a methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries. It has a role as a flavouring agent, a fragrance, an insect attractant, a volatile oil component and an anti-inflammatory agent. It is a methyl ester and an alkyl cinnamate.

Preparation

Methyl cinnamate is synthesized by esterification of cinnamic acid with methanol using HCl as catalyst, or by adding HCl to a boiling solution of cinnamyl nitrile in methanol.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 1133, 1974 DOI: 10.1021/ja00811a029
Tetrahedron Letters, 29, p. 6119, 1988 DOI: 10.1016/S0040-4039(00)82281-9

General Description

Methyl cinnamate is an important flavoring agent and fragrance ingredient. It is one of the main aroma components of basil oil, Japanese and Korean matsutake mushrooms.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Methyl cinnamate(103-26-4)Related Product Information

• Cinnamyl cinnamate
• Kresoxim-methyl
• PHENYL VALERATE
• Methyl salicylate
• Pirimiphos-methyl
• trans-Cinnamic acid
• Thiophanate-methyl
• Tribenuron methyl
• Methyl acetate
• Methyl benzoate
• Methyl formate
• Propyl cinnamate
• Methyl acrylate
• Octyl 4-methoxycinnamate
• Benzyl cinnamate
• Ethyl cinnamate
• METSULFURON METHYL
• Cinnamic acid