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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
Molecular Weight:
162.19
MDL Number:
MFCD00008458
MOL File:
103-26-4.mol
MSDS File:
SDS
Last updated:2024-12-18 14:08:52

Methyl cinnamate 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
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
Specific Gravity 1.092
color White to light yellow
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)
Substances Added to Food (formerly EAFUS) METHYL CINNAMATE
FDA 21 CFR 172.515
EWG's Food Scores 1
FDA UNII 533CV2ZCQL
NIST Chemistry Reference 2-Propenoic acid, 3-phenyl-, methyl ester(103-26-4)
EPA Substance Registry System Methyl cinnamate (103-26-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H317
Precautionary statements  P280
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.
NFPA 704
1
0 0

Methyl cinnamate price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W269816 Methyl cinnamate natural, ≥98%, FCC, FG 103-26-4 100g $184 2024-03-01 Buy
Sigma-Aldrich W269816 Methyl cinnamate natural, ≥98%, FCC, FG 103-26-4 1kg $934 2024-03-01 Buy
Sigma-Aldrich 96410 Methyl cinnamate ≥99.0% (GC) 103-26-4 100g $34.3 2024-03-01 Buy
Sigma-Aldrich 80835 Methyl cinnamate analytical standard 103-26-4 250mg $79.1 2022-05-15 Buy
TCI Chemical C0360 Methyl Cinnamate >99.0%(GC) 103-26-4 25g $17 2024-03-01 Buy
Product number Packaging Price Buy
W269816 100g $184 Buy
W269816 1kg $934 Buy
96410 100g $34.3 Buy
80835 250mg $79.1 Buy
C0360 25g $17 Buy

Methyl cinnamate Chemical Properties,Uses,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.

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.

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.

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%.

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View Lastest Price from Methyl cinnamate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Methyl cinnamate pictures 2025-01-21 Methyl cinnamate
103-26-4
US $55.00 / kg 1kg 99% 5000kg/week Hebei Zhuanglai Chemical Trading Co.,Ltd
Methyl cinnamate pictures 2025-01-20 Methyl cinnamate
103-26-4
US $0.00 / kg 1kg 99%min 10000kg WUHAN FORTUNA CHEMICAL CO., LTD
Methyl cinnamate pictures 2024-11-19 Methyl cinnamate
103-26-4
US $44.00 / g 99.95% 10g TargetMol Chemicals Inc.
  • Methyl cinnamate pictures
  • Methyl cinnamate
    103-26-4
  • US $55.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
Methyl cinnaMate >=99.0% (GC) Methyl cinnaMate, >=99%,FCC,Kosher,FG Methyl cinmate METHYL TRANS-3-PHENYLACRYLATE METHYL TRANS-3-PHENYLPROPENOATE FEMA 2698 METHYL-3-PHENYL PROP-2-ENOATE METHYL 3-PHENYLPROPENOATE METHYL-3-PHENYLPROPENOTE METHYL CINNAMATE METHYL CINNAMYLATE methl β-phenylacrylate METHYL CINNAMATE 99% METHYL CINNAMATE 98+% NATURAL FCC BETA-PHENYLMETHYLACRYLATE Methyl cinnamate, predominantly trans, 99% METHYL CINNAMATE, NATURAL METHYL CINNAMATE / CINNAMIC ACID METHYL ESTER 3-Phenyl-2-propenoic acid methyl ester 3-Phenyl-2-propenoic acid methyl 3-Phenylacrylic acid methyl ester Benzeneacrylic acid methyl ester Methyl cinnamate,98% 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 CINNAMIC ACID METHYLESTER(RG) methyl cinanmate Methyl cinnaMate, 98% 500GR Cinnamic Acid Methyl Ester Methyl trans-3-Phenylacrylate trans-3-Phenylacrylic Acid Methyl Ester CINNAMIC ACID METHYLESTER(SG) Methyl (2E)-3-phenylprop-2-enoate Methyl Cinnamate > METHYL CINNAMATE 103-26-4 Methyl cinnamate USP/EP/BP Methyl Cimnamate TIANFU-CHEM Methyl cinnamate 2,3-D methyl ester (Z)-3-phenyl-2-propenoic acid methyl ester Natural Methyl Cinnamate Ethyl trans-&beta METHYL TRANS-CINNAMATE CINNAMIC ACID METHYL ESTER METHYL 3-PHENYLACRYLATE Methyl Cinamate FEMA 2618 8022-15-9 103-26-4 103-26-5 103-26-7 103-26-6 C10H10O1 C6H5CHCHCOOCH3 C6H5C2H2COOCH3 Carbonyl Compounds
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