Methyl cinnamate
Chemical Properties Preparative Methods- Product Name
- Methyl cinnamate
- CAS No.
- 103-26-4
- Chemical Name
- Methyl cinnamate
- Synonyms
- METHYL TRANS-CINNAMATE;METHYL 3-PHENYLACRYLATE;Methyl Cinamate;CINNAMIC ACID METHYL ESTER;FEMA 2698;Methyl cinmate;METHYL CINNAMATE;methyl cinanmate;Methyl Cimnamate;Ethyl trans-&beta
- CBNumber
- CB5206328
- Molecular Formula
- C10H10O2
- Formula Weight
- 162.19
- MOL File
- 103-26-4.mol
Methyl cinnamate Property
- 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
- 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.
N-Bromosuccinimide Price
- Product number
- W269816
- Product name
- Methyl cinnamate
- Purity
- natural, ≥98%, FCC, FG
- Packaging
- 100g
- Price
- $184
- Updated
- 2024/03/01
- Product number
- W269816
- Product name
- Methyl cinnamate
- Purity
- natural, ≥98%, FCC, FG
- Packaging
- 1kg
- Price
- $934
- Updated
- 2024/03/01
- Product number
- 96410
- Product name
- Methyl cinnamate
- Purity
- ≥99.0% (GC)
- Packaging
- 100g
- Price
- $34.3
- Updated
- 2024/03/01
- Product number
- 80835
- Product name
- Methyl cinnamate
- Purity
- analytical standard
- Packaging
- 250mg
- Price
- $79.1
- Updated
- 2022/05/15
- Product number
- C0360
- Product name
- Methyl Cinnamate
- Purity
- >99.0%(GC)
- Packaging
- 25g
- Price
- $17
- Updated
- 2024/03/01
Methyl cinnamate Chemical Properties,Usage,Production
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.
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%.
Methyl cinnamate Preparation Products And Raw materials
Raw materials
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View Lastest Price from Methyl cinnamate manufacturers
- Product
- Methyl cinnamate 103-26-4
- Price
- US $55.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000kg/week
- Release date
- 2024-06-03
- Product
- Methyl cinnamate 103-26-4
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 50000KG/month
- Release date
- 2023-07-04
- Product
- Methyl cinnamate 103-26-4
- Price
- US $5.90-3.20/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10 tons
- Release date
- 2024-06-25