| Identification | More | [Name]
Methyl cinnamate | [CAS]
103-26-4 | [Synonyms]
CINNAMIC ACID METHYL ESTER
FEMA 2698
METHYL 3-PHENYLACRYLATE
METHYL-3-PHENYL PROP-2-ENOATE
METHYL 3-PHENYLPROPENOATE
METHYL-3-PHENYLPROPENOTE
METHYL CINNAMATE
METHYL CINNAMYLATE
METHYL TRANS-3-PHENYLACRYLATE
METHYL TRANS-3-PHENYLPROPENOATE
METHYL TRANS-CINNAMATE
TRANS-3-PHENYLACRYLIC ACID METHYL ESTER
2-Propenoicacid,3-phenyl-,methylester
3-phenyl-2-propenoicacimethylester
3-phenyl-prop-2-enoicacidmethylester
Methyl 3-phenyl-2-propenoate
Methyl ester of Cinnamic acid
methyl3-phenyl-2-propenoate
methl β-phenylacrylate
METHYL CINNAMATE 99% | [EINECS(EC#)]
203-093-8 | [Molecular Formula]
C10H10O2 | [MDL Number]
MFCD00008458 | [Molecular Weight]
162.19 | [MOL File]
103-26-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light yellow fused crystalline mas | [Melting point ]
33-38 °C (lit.) | [Boiling point ]
260-262 °C (lit.) | [density ]
1.092 | [vapor pressure ]
0.73Pa at 25℃ | [FEMA ]
2698 | [refractive index ]
1.5771 | [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [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 | [Detection Methods]
GC | [JECFA Number]
658 | [Merck ]
14,2299 | [BRN ]
386468 | [InChIKey]
CCRCUPLGCSFEDV-BQYQJAHWSA-N | [LogP]
2.68 at 25℃ | [Uses]
Perfumes, flavoring. | [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]
103-26-4(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1 | [RTECS ]
GE0190000 | [TSCA ]
Yes | [HS Code ]
29163990 | [Safety Profile]
Moderately toxic by
ingestion. Combustible liquid. When heated
to decomposition it emits acrid smoke and
irritating fumes. | [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. |
| Questions And Answer | Back Directory | [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%.
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| Hazard Information | Back Directory | [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. | [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. | [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]
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]
Nonflammable | [Synthesis]
Take 14.8g of cinnamic acid, 12.8g of methanol and 0.74g of supported acidic catalyst, respectively, add them to a 250ml flask, heat and reflux for 3h, and then perform vacuum distillation until no liquid is distilled out. Filter while hot to remove the solid catalyst and maintain the liquid phase temperature at 43℃. Add 6% KCO3 solution to the product until the solution pH is 8.5 while maintaining the solution temperature at 43℃, let stand and separate, remove the water phase, wash the product with twice the volume of 42℃ deionized water, let stand and separate, remove the water phase, and repeat this step until the solution pH is 7. Add three times the volume of 10℃ deionized water to the product under continuous stirring, and a light yellow solid will precipitate, methyl cinnamate, with a yield of 86%.
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