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Ethyl gallate

CAS# 831-61-8

Ethyl gallate

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Quality Control of Ethyl gallate

Number of papers citing our products

Chemical structure

Ethyl gallate

3D structure

Chemical Properties of Ethyl gallate

Cas No. 831-61-8 SDF Download SDF
PubChem ID 13250 Appearance White powder
Formula C9H10O5 M.Wt 198.2
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms Ethyl 3,4,5-trihydroxybenzoate; Gallic acid ethyl ester; 3,4,5-Trihydroxybenzoic acid ethyl ester
Solubility DMSO : 150 mg/mL (756.93 mM; Need ultrasonic)
Chemical Name ethyl 3,4,5-trihydroxybenzoate
SMILES CCOC(=O)C1=CC(=C(C(=C1)O)O)O
Standard InChIKey VFPFQHQNJCMNBZ-UHFFFAOYSA-N
Standard InChI InChI=1S/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3
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 gallate

The herbs of Coriaria nepalensis

Biological Activity of Ethyl gallate

DescriptionEthyl gallate has anti-cancer, antioxidant activities, it may be an alternative class of vasopressors for use in septic shock. Ethyl gallate can treat acute lung injury (ALI) mainly by reducing the total cells and infiltration of activated polymorphonuclear leukocytes (PMNs). Ethyl gallate inhibits Akt , NF-κB p-65, Bcl-2/Bax, and mRNA levels of MMP-2 and MMP-9.
TargetsNF-kB | p65 | Bcl-2/Bax | PI3K | Akt | MMP(e.g.TIMP)
In vitro

Ethyl gallate suppresses proliferation and invasion in human breast cancer cells via Akt-NF-κB signaling.[Pubmed: 25522911]

Oncol Rep. 2015 Mar;33(3):1284-90.

Euphorbia fischeriana Steud is a traditional Chinese Medicine that is known to possess a variety of anticarcinogenic properties. However, the bioactive constituents in Euphorbia fischeriana Steud and molecular mechanisms underlying this action in cancer treatment remain poorly understood. The present study investigated the chemotherapy activity and molecular targets of Ethyl gallate, which is identified as the major constituent extracted from the roots of Euphorbia fischeriana Steud in breast cancer cell lines in vitro.
METHODS AND RESULTS:
The results showed Ethyl gallate obviously decreased cell proliferation in MDA-MB-231 and MCF-7 cells in a dose- and time-dependent manner. Highly invasive MDA-MB-231 cells were found to be highly sensitive to treatment. Furthermore, significantly decreased metastatic potential of highly metastatic MDA-MB‑231 cells by Ethyl gallate was identified via the inhibition of cell motility using invasion and migration through a polyethylene terephthalate membrane. Ethyl gallate treatment decreased the activity of matrix metalloproteinase-2 (MMP-2) and MMP-9 by the downregulation of mRNA levels using RT-PCR, enzymes that are critical to tumor invasion. Treatment with Ethyl gallate decreased phosphatidylinositol 3-kinase (PI3K)/Akt and nuclear factor-κB (NF-κB) activation in MDA-MB-231 cells. These results indicate that Ethyl gallate suppresses proliferation and invasion in human breast cancer cells by modulating the PI3K/Akt pathway, which may contribute to inhibiting their downstream targets such as NF-κB p-65, Bcl-2/Bax, and mRNA levels of MMP-2 and MMP-9 in breast cancer cells.
CONCLUSIONS:
Thus, the present study shed new light on Ethyl gallate, an important bioactive constituent of Euphorbia fischeriana Steud, in human breast cancer treatment. The findings may provide basal theories for wide therapeutic application in human breast cancer.

In vivo

In vitro protection of biological macromolecules against oxidative stress and in vivo toxicity evaluation of Acacia nilotica (L.) and ethyl gallate in rats.[Pubmed: 25043389]

BMC Complement Altern Med. 2014 Jul 21;14:257.

Recently, enormous research has been focused on natural bioactive compounds possessing potential antioxidant and anticancer properties using cell lines and animal models. Acacia nilotica (L.) is widely distributed in Asia, Africa, Australia and Kenya. The plant is traditionally used to treat mouth, ear and bone cancer. However, reports on Acacia nilotica (L.) Wild. Ex. Delile subsp. indica (Benth.) Brenan regarding its toxicity profile is limited. Hence in this study, we investigated the antioxidant capacity and acute toxicity of Ethyl gallate, a phenolic antioxidant present in the A. nilotica (L.) leaf extract.
METHODS AND RESULTS:
The antioxidant activity of Ethyl gallate against Fenton's system (Fe3+/H2O2/ascorbic acid) generated oxidative damage to pBR322 DNA and BSA was investigated. We also studied the interaction of Ethyl gallate to CT-DNA by wave scan and FTIR analysis. The amount of Ethyl gallate present in the A. nilotica (L.) leaf extract was calculated using HPLC and represented in gram equivalence of Ethyl gallate. The acute toxicity profile of Ethyl gallate in the A. nilotica (L.) leaf extract was analyzed in albino Wistar rats. Measurement of liver and kidney function markers, total proteins and glucose were determined in the serum. Statistical analysis was done using statistical package for social sciences (SPSS) tool version 16.0. Ethyl gallate was found to be effective at 100 μg/mL concentration by inhibiting the free radical mediated damage to BSA and pBR322 DNA. We also found that the interaction of Ethyl gallate and A. nilotica (L.) leaf extract to CT-DNA occurs through intercalation. One gram of A. nilotica (L.) leaf extract was found to be equivalent to 20 mg of Ethyl gallate through HPLC analysis. Based on the acute toxicity results, A. nilotica (L.) leaf extract and Ethyl gallate as well was found to be non-toxic and safe.
CONCLUSIONS:
Results revealed no mortality or abnormal biochemical changes in vivo and the protective effect of A. nilotica (L.) leaf extract and Ethyl gallate on DNA and protein against oxidative stress in vitro. Hence, A. nilotica (L.) leaf extract or Ethyl gallate could be used as potential antioxidants with safe therapeutic application in cancer chemotherapy.

Bioactive Components from Qingwen Baidu Decoction against LPS-Induced Acute Lung Injury in Rats.[Pubmed: 28445422 ]

Molecules. 2017 Apr 26;22(5). pii: E692.

Qingwen Baidu Decoction (QBD) is an extraordinarily "cold" formula. It was traditionally used to cure epidemic hemorrhagic fever, intestinal typhoid fever, influenza, sepsis and so on. The purpose of this study was to discover relationships between the change of the constituents in different extracts of QBD and the pharmacological effect in a rat model of acute lung injury (ALI) induced by lipopolysaccharide (LPS).
METHODS AND RESULTS:
The study aimed to discover the changes in constituents of different QBD extracts and the pharmacological effects on acute lung injury (ALI) induced by LPS. The results demonstrated that high dose and middle dose of QBD had significantly potent anti-inflammatory effects and reduced pulmonary edema caused by ALI in rats (p < 0.05). To explore the underlying constituents of QBD, we assessed its influence of six different QBD extracts on ALI and analyzed the different constituents in the corresponding HPLC chromatograms by a Principal Component Analysis (PCA) method. The results showed that the pharmacological effect of QBD was related to the polarity of its extracts, and the medium polarity extracts E2 and E5 in particular displayed much better protective effects against ALI than other groups. Moreover, HPLC-DAD-ESI-MSn and PCA analysis showed that verbascoside and angoroside C played a key role in reducing pulmonary edema.
CONCLUSIONS:
In addition, the current study revealed that Ethyl gallate, pentagalloylglucose, galloyl paeoniflorin, mudanpioside C and harpagoside can treat ALI mainly by reducing the total cells and infiltration of activated polymorphonuclear leukocytes (PMNs).

Protocol of Ethyl gallate

Kinase Assay

Effect of ethyl gallate on invasion abilities and its mechanism of breast cancer MDA-MB-231 cells.[Pubmed: 25924474]

Yao Xue Xue Bao. 2015 Jan;50(1):45-9.

This study is to investigate the effect of Ethyl gallate on invasion capabilities and its mechanism of breast cancer MDA-MB-231 cells.
METHODS AND RESULTS:
Using cell adhesion and transwell assay, separately, the effects of Ethyl gallate on the invasion of MDA-MB-231 cells were measured. The Akt-NF-κB signal pathway protein expressions were analyzed with Western blot. Also, the mRNA levels of MMP-9 and MMP-2 were analyzed by RT-PCR. Ethyl gallate inhibited the abilities of motility, adhesion and invasion of breast cancer MDA-MB-231 cells in vitro (P<0.05), inhibited the mRNA levels of MMP-9, MMP-2, phosphorylation of AKt and protein expression of NF-κB.
CONCLUSIONS:
It is concluded that Ethyl gallate can inhibit the abilities of invasion of breast cancer in vitro by inhibiting the mRNA levels of MMP-9/MMP-2, phosphorylation of Akt and protein expression of NF-κB.

Cell Research

In vitro evaluation of antiproliferative effect of ethyl gallate against human oral squamous carcinoma cell line KB.[Pubmed: 25104086 ]

Nat Prod Res. 2015;29(4):366-9.

Although some polyphenols are known to possess anticancer activity against different cancer cell lines through induction of apoptosis, the mode of antiproliferative effect of Ethyl gallate against human oral squamous carcinoma cell line KB was not studied until now. Therefore, the antiproliferative effect of Ethyl gallate was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay in comparison with the reference drug paclitaxel.
METHODS AND RESULTS:
Generation of reactive oxygen species, mitochondrial membrane potential loss, DNA damage and apoptosis were determined using 2,7-diacetyldichlorofluorescein fluorescence, uptake of rhodamine-123 by mitochondria, comet assay and acridine orange/ethidium bromide dual-dye staining method. Both Ethyl gallate and paclitaxel exhibited cytotoxicity in a dose-dependent manner. The 50% inhibitory concentration for Ethyl gallate was 30 and 20 μg/mL for paclitaxel.
CONCLUSIONS:
A volume of 50 μg/mL of Ethyl gallate was found to be significantly effective (P < 0.05) in controlling the cancer cell proliferation leading to acute apoptosis.

Animal Research

Benefits of ethyl gallate versus norepinephrine in the treatment of cardiovascular collapse in Pseudomonas aeruginosa septic shock in dogs.[Pubmed: 22020237]

Crit Care Med. 2012 Feb;40(2):560-72.

Vasopressor therapy is required in septic shock to maintain tissue perfusion in the face of hypotension. Unfortunately, there are significant side effects of current vasopressors, and newer agents need to be developed. We recently discovered that Ethyl gallate, a nonflavonoid phenolic antioxidant found in food substances, could reverse low mean arterial pressure found in an experimental model of septic shock due to inhibition of hydrogen peroxide signaling. In the present study, we compared the hemodynamic and biochemical effects of Ethyl gallate vs. those of the commonly used vasopressor, norepinephrine, in a bacteremic canine model of Pseudomonas aeruginosa sepsis in two protocols.
METHODS AND RESULTS:
We performed these studies in anesthetized and mechanically ventilated dogs. In the early treatment protocol, we infused P. aeruginosa until mean arterial pressure first decreased to ~60 mm Hg (about 2-3 hrs), after which we stopped the infusion and randomly administered Ethyl gallate or norepinephrine in respective groups. In the late treatment protocol, we administered Ethyl gallate or norepinephrine after a sustained ~5-hr decrease in mean arterial pressure to 60 mm Hg and continued the infusion for the duration of the experiment. We followed parameters for over 10 hrs after the initiation of P. aeruginosa in both groups. We measured stroke work, urine output, serum creatinine, among other parameters, and used serum troponin T as an index of myocardial injury. We found that in both protocols, Ethyl gallate and norepinephrine improved mean arterial pressure and stroke work to similar extents over the duration of the study. Particularly in the late treatment protocol, Ethyl gallate resulted in a lower heart rate, a lower troponin T, and a greater urine output as compared with norepinephrine (p < .05).
CONCLUSIONS:
These results suggest that phenolic antioxidants, such as Ethyl gallate, that inhibit hydrogen peroxide signaling, may represent an alternative class of vasopressors for use in septic shock.

Ethyl gallate Dilution Calculator

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Preparing Stock Solutions of Ethyl gallate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.0454 mL 25.227 mL 50.4541 mL 100.9082 mL 126.1352 mL
5 mM 1.0091 mL 5.0454 mL 10.0908 mL 20.1816 mL 25.227 mL
10 mM 0.5045 mL 2.5227 mL 5.0454 mL 10.0908 mL 12.6135 mL
50 mM 0.1009 mL 0.5045 mL 1.0091 mL 2.0182 mL 2.5227 mL
100 mM 0.0505 mL 0.2523 mL 0.5045 mL 1.0091 mL 1.2614 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 gallate

Benefits of ethyl gallate versus norepinephrine in the treatment of cardiovascular collapse in Pseudomonas aeruginosa septic shock in dogs.[Pubmed:22020237]

Crit Care Med. 2012 Feb;40(2):560-72.

INTERVENTIONS: Vasopressor therapy is required in septic shock to maintain tissue perfusion in the face of hypotension. Unfortunately, there are significant side effects of current vasopressors, and newer agents need to be developed. We recently discovered that Ethyl gallate, a nonflavonoid phenolic antioxidant found in food substances, could reverse low mean arterial pressure found in an experimental model of septic shock due to inhibition of hydrogen peroxide signaling. In the present study, we compared the hemodynamic and biochemical effects of Ethyl gallate vs. those of the commonly used vasopressor, norepinephrine, in a bacteremic canine model of Pseudomonas aeruginosa sepsis in two protocols. MEASUREMENTS AND MAIN RESULTS: We performed these studies in anesthetized and mechanically ventilated dogs. In the early treatment protocol, we infused P. aeruginosa until mean arterial pressure first decreased to approximately 60 mm Hg (about 2-3 hrs), after which we stopped the infusion and randomly administered Ethyl gallate or norepinephrine in respective groups. In the late treatment protocol, we administered Ethyl gallate or norepinephrine after a sustained approximately 5-hr decrease in mean arterial pressure to 60 mm Hg and continued the infusion for the duration of the experiment. We followed parameters for over 10 hrs after the initiation of P. aeruginosa in both groups. We measured stroke work, urine output, serum creatinine, among other parameters, and used serum troponin T as an index of myocardial injury. We found that in both protocols, Ethyl gallate and norepinephrine improved mean arterial pressure and stroke work to similar extents over the duration of the study. Particularly in the late treatment protocol, Ethyl gallate resulted in a lower heart rate, a lower troponin T, and a greater urine output as compared with norepinephrine (p < .05). CONCLUSIONS: These results suggest that phenolic antioxidants, such as Ethyl gallate, that inhibit hydrogen peroxide signaling, may represent an alternative class of vasopressors for use in septic shock.

In vitro evaluation of antiproliferative effect of ethyl gallate against human oral squamous carcinoma cell line KB.[Pubmed:25104086]

Nat Prod Res. 2015;29(4):366-9.

Although some polyphenols are known to possess anticancer activity against different cancer cell lines through induction of apoptosis, the mode of antiproliferative effect of Ethyl gallate against human oral squamous carcinoma cell line KB was not studied until now. Therefore, the antiproliferative effect of Ethyl gallate was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay in comparison with the reference drug paclitaxel. Generation of reactive oxygen species, mitochondrial membrane potential loss, DNA damage and apoptosis were determined using 2,7-diacetyldichlorofluorescein fluorescence, uptake of rhodamine-123 by mitochondria, comet assay and acridine orange/ethidium bromide dual-dye staining method. Both Ethyl gallate and paclitaxel exhibited cytotoxicity in a dose-dependent manner. The 50% inhibitory concentration for Ethyl gallate was 30 and 20 mug/mL for paclitaxel. A volume of 50 mug/mL of Ethyl gallate was found to be significantly effective (P < 0.05) in controlling the cancer cell proliferation leading to acute apoptosis.

In vitro protection of biological macromolecules against oxidative stress and in vivo toxicity evaluation of Acacia nilotica (L.) and ethyl gallate in rats.[Pubmed:25043389]

BMC Complement Altern Med. 2014 Jul 21;14:257.

BACKGROUND: Recently, enormous research has been focused on natural bioactive compounds possessing potential antioxidant and anticancer properties using cell lines and animal models. Acacia nilotica (L.) is widely distributed in Asia, Africa, Australia and Kenya. The plant is traditionally used to treat mouth, ear and bone cancer. However, reports on Acacia nilotica (L.) Wild. Ex. Delile subsp. indica (Benth.) Brenan regarding its toxicity profile is limited. Hence in this study, we investigated the antioxidant capacity and acute toxicity of Ethyl gallate, a phenolic antioxidant present in the A. nilotica (L.) leaf extract. METHODS: The antioxidant activity of Ethyl gallate against Fenton's system (Fe3+/H2O2/ascorbic acid) generated oxidative damage to pBR322 DNA and BSA was investigated. We also studied the interaction of Ethyl gallate to CT-DNA by wave scan and FTIR analysis. The amount of Ethyl gallate present in the A. nilotica (L.) leaf extract was calculated using HPLC and represented in gram equivalence of Ethyl gallate. The acute toxicity profile of Ethyl gallate in the A. nilotica (L.) leaf extract was analyzed in albino Wistar rats. Measurement of liver and kidney function markers, total proteins and glucose were determined in the serum. Statistical analysis was done using statistical package for social sciences (SPSS) tool version 16.0. RESULTS: Ethyl gallate was found to be effective at 100 mug/mL concentration by inhibiting the free radical mediated damage to BSA and pBR322 DNA. We also found that the interaction of Ethyl gallate and A. nilotica (L.) leaf extract to CT-DNA occurs through intercalation. One gram of A. nilotica (L.) leaf extract was found to be equivalent to 20 mg of Ethyl gallate through HPLC analysis. Based on the acute toxicity results, A. nilotica (L.) leaf extract and Ethyl gallate as well was found to be non-toxic and safe. CONCLUSIONS: Results revealed no mortality or abnormal biochemical changes in vivo and the protective effect of A. nilotica (L.) leaf extract and Ethyl gallate on DNA and protein against oxidative stress in vitro. Hence, A. nilotica (L.) leaf extract or Ethyl gallate could be used as potential antioxidants with safe therapeutic application in cancer chemotherapy.

Ethyl gallate suppresses proliferation and invasion in human breast cancer cells via Akt-NF-kappaB signaling.[Pubmed:25522911]

Oncol Rep. 2015 Mar;33(3):1284-90.

Euphorbia fischeriana Steud is a traditional Chinese Medicine that is known to possess a variety of anticarcinogenic properties. However, the bioactive constituents in Euphorbia fischeriana Steud and molecular mechanisms underlying this action in cancer treatment remain poorly understood. The present study investigated the chemotherapy activity and molecular targets of Ethyl gallate, which is identified as the major constituent extracted from the roots of Euphorbia fischeriana Steud in breast cancer cell lines in vitro. The results showed Ethyl gallate obviously decreased cell proliferation in MDA-MB-231 and MCF-7 cells in a dose- and time-dependent manner. Highly invasive MDA-MB-231 cells were found to be highly sensitive to treatment. Furthermore, significantly decreased metastatic potential of highly metastatic MDA-MB231 cells by Ethyl gallate was identified via the inhibition of cell motility using invasion and migration through a polyethylene terephthalate membrane. Ethyl gallate treatment decreased the activity of matrix metalloproteinase-2 (MMP-2) and MMP-9 by the downregulation of mRNA levels using RT-PCR, enzymes that are critical to tumor invasion. Treatment with Ethyl gallate decreased phosphatidylinositol 3-kinase (PI3K)/Akt and nuclear factor-kappaB (NF-kappaB) activation in MDA-MB-231 cells. These results indicate that Ethyl gallate suppresses proliferation and invasion in human breast cancer cells by modulating the PI3K/Akt pathway, which may contribute to inhibiting their downstream targets such as NF-kappaB p-65, Bcl-2/Bax, and mRNA levels of MMP-2 and MMP-9 in breast cancer cells. Thus, the present study shed new light on Ethyl gallate, an important bioactive constituent of Euphorbia fischeriana Steud, in human breast cancer treatment. The findings may provide basal theories for wide therapeutic application in human breast cancer.

[Effect of ethyl gallate on invasion abilities and its mechanism of breast cancer MDA-MB-231 cells].[Pubmed:25924474]

Yao Xue Xue Bao. 2015 Jan;50(1):45-9.

This study is to investigate the effect of Ethyl gallate on invasion capabilities and its mechanism of breast cancer MDA-MB-231 cells. Using cell adhesion and transwell assay, separately, the effects of Ethyl gallate on the invasion of MDA-MB-231 cells were measured. The Akt-NF-kappaB signal pathway protein expressions were analyzed with Western blot. Also, the mRNA levels of MMP-9 and MMP-2 were analyzed by RT-PCR. Ethyl gallate inhibited the abilities of motility, adhesion and invasion of breast cancer MDA-MB-231 cells in vitro (P<0.05), inhibited the mRNA levels of MMP-9, MMP-2, phosphorylation of AKt and protein expression of NF-kappaB. It is concluded that Ethyl gallate can inhibit the abilities of invasion of breast cancer in vitro by inhibiting the mRNA levels of MMP-9/MMP-2, phosphorylation of Akt and protein expression of NF-kappaB.

Description

Ethyl gallate is a nonflavonoid phenolic compound and also a scavenger of hydrogen peroxide.

Keywords:

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