Methyl cinnamate

Methyl cinnamate Basic information
Chemical Properties Preparative Methods
Product Name:Methyl cinnamate
Synonyms:METHYL TRANS-3-PHENYLACRYLATE;METHYL TRANS-3-PHENYLPROPENOATE;METHYL TRANS-CINNAMATE;FEMA 2698;CINNAMIC ACID METHYL ESTER;METHYL 3-PHENYLACRYLATE;METHYL-3-PHENYL PROP-2-ENOATE;METHYL 3-PHENYLPROPENOATE
CAS:103-26-4
MF:C10H10O2
MW:162.19
EINECS:203-093-8
Product Categories:Cinnamic acid;FINE Chemical & INTERMEDIATES;Alphabetical Listings;Certified Natural ProductsFlavors and Fragrances;Flavors and Fragrances;M-N;Benzene derivatives;Cosmetics;103-26-4
Mol File:103-26-4.mol
Methyl cinnamate Structure
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℃
FEMA 2698 | METHYL CINNAMATE
refractive index 1.5771
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Fused Crystalline Mass
Specific Gravity1.092
color White to light yellow
Odorat 100.00 %. sweet balsam strawberry cherry cinnamon
Odor Typebalsamic
Water Solubility insoluble
Merck 14,2299
JECFA Number658
BRN 386468
InChIKeyCCRCUPLGCSFEDV-BQYQJAHWSA-N
LogP2.68 at 25℃
CAS DataBase Reference103-26-4(CAS DataBase Reference)
NIST Chemistry Reference2-Propenoic acid, 3-phenyl-, methyl ester(103-26-4)
EPA Substance Registry SystemMethyl cinnamate (103-26-4)
Safety Information
Safety Statements 22-24/25
WGK Germany 1
RTECS GE0190000
TSCA Yes
HS Code 29163990
ToxicityModerately 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 Information
ProviderLanguage
3-Phenyl-2-propenoic acid methyl ester English
SigmaAldrich English
ACROS English
ALFA English
Methyl cinnamate Usage And Synthesis
Chemical PropertiesMethyl 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 MethodsIt 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%.
DescriptionMethyl 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 PropertiesMethyl cinnamate has a fruity, balsamic odor similar to strawberry and a corresponding sweet taste.
OccurrenceReported 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.
UsesMethyl cinnamate is used as a fragrance ingredient in cosmetics and household products.
UsesMethyl 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.
DefinitionChEBI: 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.
PreparationMethyl 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 DescriptionMethyl 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 ExplosibilityNonflammable
Safety ProfileModerately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
trans-Cinnamic acid Propyl cinnamate Methyl 4-hydroxycinnamate Methyl Parathion-methyl Tribenuron methyl Kresoxim-methyl PHENYL VALERATE Thiophanate-methyl Pirimiphos-methyl Methyl benzoate METHYL 4-METHYLCINNAMATE Methyl salicylate Methyl acrylate Methyl formate Methyl acetate Methyl bromide Phenylacetic acid

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