Ethyl cinnamate

CAS# 103-36-6

Ethyl cinnamate

Catalog No. BCN5044----Order now to get a substantial discount!

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Chemical structure

Ethyl cinnamate

3D structure

Chemical Properties of Ethyl cinnamate

Cas No. 103-36-6 SDF Download SDF
PubChem ID 637758 Appearance Oil
Formula C11H12O2 M.Wt 176.21
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name ethyl (E)-3-phenylprop-2-enoate
SMILES CCOC(=O)C=CC1=CC=CC=C1
Standard InChIKey KBEBGUQPQBELIU-CMDGGOBGSA-N
Standard InChI InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Ethyl cinnamate

The barks of Cinnamomum cassia Presl

Biological Activity of Ethyl cinnamate

DescriptionEthyl cinnamate has antifungal, and vasorelaxant effects, it can inhibit the tonic contractions induced by high K+ and phenylephrine (PE) in a concentration-dependent manner, with respective IC50 values of 0.30 +/- 0.05 mM and 0.38 +/- 0.04 mM. Ethyl cinnamate can lead to the damage of cell membrane system and metabolic disorder through inducing lipid peroxidation via initiating ROS overproduction.Ethyl cinnamate has acute inhibition to the maximum quantum yield and the potential activity of photosystem II of Chlorella pyrenoidosa.
TargetsROS | NO | Calcium Channel | Potassium Channel | Antifection
In vitro

Toxic Effects of Ethyl Cinnamate on the Photosynthesis and Physiological Characteristics of Chlorella vulgaris Based on Chlorophyll Fluorescence and Flow Cytometry Analysis.[Pubmed: 26101784]

ScientificWorldJournal. 2015;2015:107823.

The toxic effects of Ethyl cinnamate on the photosynthetic and physiological characteristics of Chlorella vulgaris were studied based on chlorophyll fluorescence and flow cytometry analysis.
METHODS AND RESULTS:
Parameters, including biomass, F(v)/F(m) (maximal photochemical efficiency of PSII), Ф(PSII) (actual photochemical efficiency of PSII in the light), FDA, and PI staining fluorescence, were measured. The results showed the following: (1) The inhibition on biomass increased as the exposure concentration increased. 1 mg/L Ethyl cinnamate was sufficient to reduce the total biomass of C. vulgaris. The 48-h and 72-h EC50 values were 2.07 mg/L (1.94-2.20) and 1.89 mg/L (1.82-1.97). (2) After 24 h of exposure to 2-4 mg/L Ethyl cinnamate, the photosynthesis of C. vulgaris almost ceased, manifesting in Ф(PSII) being close to zero. After 72 h of exposure to 4 mg/L Ethyl cinnamate, the Fv /Fm of C. vulgaris dropped to zero. (3) Ethyl cinnamate also affected the cellular physiology of C. vulgaris, but these effects resulted in the inhibition of cell yield rather than cell death.
CONCLUSIONS:
Exposure to Ethyl cinnamate resulted in decreased esterase activities in C. vulgaris, increased average cell size, and altered intensities of chlorophyll a fluorescence. Overall, esterase activity was the most sensitive variable.

Effects of allelochemicals ethyl cinnamate on the growth and physiological characteristics of Chlorella pyrenoidosa.[Pubmed: 23487932]

Huan Jing Ke Xue. 2013 Jan;34(1):156-62.

The effects of Ethyl cinnamate on the growth and physiological characteristics of Chlorella pyrenoidosa were studied. The allelopathic mechanisms were explored, from views of chlorophyll a content, antioxidant enzyme activities, reactive oxygen species (ROS) level, malondialdehyde (MDA) content and photosynthetic activity.
METHODS AND RESULTS:
The results revealed that Ethyl cinnamate had acute inhibitory effects on the growth of Chlorella pyrenoidosa, and the inhibited degree tended to increase with increased concentrations. The effective concentration causing a 50% inhibition at 96 h was 5.45 mg c L(-1). Ethyl cinnamate induced the decrease of chlorophyll a, the over-accumulation of ROS and the increase of MDA. Therefore, it suggested that Ethyl cinnamate could lead to the damage of cell membrane system and metabolic disorder through inducing lipid peroxidation via initiating ROS overproduction. And for scavenging ROS, the algae cells were protected from oxidative damages through increasing the activity of antioxidant enzymes.
CONCLUSIONS:
The results demonstrated Ethyl cinnamate had acute inhibition to the maximum quantum yield and the potential activity of photosystem II of Chlorella pyrenoidosa, however, the photosynthetic activity could recover to some extent through self-regulation after some time.

Antifungal properties of Ocimum gratissimum essential oil (ethyl cinnamate chemotype).[Pubmed: 11449510]

Fitoterapia. 2000 Sep;71(5):567-9.

Largely widespread in tropical countries, Ocimum gratissimum has been claimed for many uses in folk medicine. Recent research on its essential oils showed five chemotypes.
CONCLUSIONS:
An Indian chemotype, with a high level of Ethyl cinnamate, presents, in vitro, an interesting spectrum of antifungal properties.

In vivo

Fragrance material review on ethyl cinnamate.[Pubmed: 18037216]

Food Chem Toxicol. 2007;45 Suppl 1:S90-4.

A toxicologic and dermatologic review of Ethyl cinnamate when used as a fragrance ingredient is presented.

Protocol of Ethyl cinnamate

Animal Research

Vasorelaxant effects of ethyl cinnamate isolated from Kaempferia galanga on smooth muscles of the rat aorta.[Pubmed: 12143006]

Planta Med. 2002 Jul;68(7):655-7.

From the rhizomes of Kaempferia galanga, Ethyl cinnamate (EC) was isolated and its vasorelaxant effect was examined on the rat aorta.
METHODS AND RESULTS:
EC inhibited the tonic contractions induced by high K+ and phenylephrine (PE) in a concentration-dependent manner, with respective IC50 values of 0.30 +/- 0.05 mM and 0.38 +/- 0.04 mM. The relaxant effect against PE-induced contractions was greater in the presence of endothelium. Pre-treatment of the aorta with methylene blue and indomethacin significantly reduced the relaxant effect. These results suggest that the inhibitory effects of EC may involve inhibition of Ca2+ influx into vascular cells and release of nitric oxide (NO) and prostacyclin from the endothelial cells.
CONCLUSIONS:
Thus, the vasorelaxant effect of EC mediated through multiple pathways may explain the traditional use of the parent plant in treating hypertension.

Ethyl cinnamate Dilution Calculator

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Ethyl cinnamate Molarity Calculator

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Preparing Stock Solutions of Ethyl cinnamate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.675 mL 28.3752 mL 56.7505 mL 113.5009 mL 141.8762 mL
5 mM 1.135 mL 5.675 mL 11.3501 mL 22.7002 mL 28.3752 mL
10 mM 0.5675 mL 2.8375 mL 5.675 mL 11.3501 mL 14.1876 mL
50 mM 0.1135 mL 0.5675 mL 1.135 mL 2.27 mL 2.8375 mL
100 mM 0.0568 mL 0.2838 mL 0.5675 mL 1.135 mL 1.4188 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Ethyl cinnamate

Fragrance material review on ethyl cinnamate.[Pubmed:18037216]

Food Chem Toxicol. 2007;45 Suppl 1:S90-4.

A toxicologic and dermatologic review of Ethyl cinnamate when used as a fragrance ingredient is presented.

Antifungal properties of Ocimum gratissimum essential oil (ethyl cinnamate chemotype).[Pubmed:11449510]

Fitoterapia. 2000 Sep;71(5):567-9.

Largely widespread in tropical countries, Ocimum gratissimum has been claimed for many uses in folk medicine. Recent research on its essential oils showed five chemotypes. An Indian chemotype, with a high level of Ethyl cinnamate, presents, in vitro, an interesting spectrum of antifungal properties.

Vasorelaxant effects of ethyl cinnamate isolated from Kaempferia galanga on smooth muscles of the rat aorta.[Pubmed:12143006]

Planta Med. 2002 Jul;68(7):655-7.

From the rhizomes of Kaempferia galanga, Ethyl cinnamate (EC) was isolated and its vasorelaxant effect was examined on the rat aorta. EC inhibited the tonic contractions induced by high K+ and phenylephrine (PE) in a concentration-dependent manner, with respective IC50 values of 0.30 +/- 0.05 mM and 0.38 +/- 0.04 mM. The relaxant effect against PE-induced contractions was greater in the presence of endothelium. Pre-treatment of the aorta with methylene blue and indomethacin significantly reduced the relaxant effect. These results suggest that the inhibitory effects of EC may involve inhibition of Ca2+ influx into vascular cells and release of nitric oxide (NO) and prostacyclin from the endothelial cells. Thus, the vasorelaxant effect of EC mediated through multiple pathways may explain the traditional use of the parent plant in treating hypertension.

Toxic Effects of Ethyl Cinnamate on the Photosynthesis and Physiological Characteristics of Chlorella vulgaris Based on Chlorophyll Fluorescence and Flow Cytometry Analysis.[Pubmed:26101784]

ScientificWorldJournal. 2015;2015:107823.

The toxic effects of Ethyl cinnamate on the photosynthetic and physiological characteristics of Chlorella vulgaris were studied based on chlorophyll fluorescence and flow cytometry analysis. Parameters, including biomass, F(v)/F(m) (maximal photochemical efficiency of PSII), capital EF, Cyrillic(PSII) (actual photochemical efficiency of PSII in the light), FDA, and PI staining fluorescence, were measured. The results showed the following: (1) The inhibition on biomass increased as the exposure concentration increased. 1 mg/L Ethyl cinnamate was sufficient to reduce the total biomass of C. vulgaris. The 48-h and 72-h EC50 values were 2.07 mg/L (1.94-2.20) and 1.89 mg/L (1.82-1.97). (2) After 24 h of exposure to 2-4 mg/L Ethyl cinnamate, the photosynthesis of C. vulgaris almost ceased, manifesting in capital EF, Cyrillic(PSII) being close to zero. After 72 h of exposure to 4 mg/L Ethyl cinnamate, the Fv /Fm of C. vulgaris dropped to zero. (3) Ethyl cinnamate also affected the cellular physiology of C. vulgaris, but these effects resulted in the inhibition of cell yield rather than cell death. Exposure to Ethyl cinnamate resulted in decreased esterase activities in C. vulgaris, increased average cell size, and altered intensities of chlorophyll a fluorescence. Overall, esterase activity was the most sensitive variable.

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