Epigallocatechin CAS NO.970-74-1

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Epigallocatechin
970-74-1
standard supplier in China

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ProName: Epigallocatechin
CasNo: 970-74-1
Molecular Formula: C15H14O7= 306.3
Appearance: detailed see specifications
Application: analysis,activity test,Botanical Refer...
DeliveryTime: 1-3?working?days?after?confirming?the?...
PackAge: According to the clients requirement.
Port: China main port
ProductionCapacity: 1 Metric Ton/Day
Purity: ≥98%
Storage: Store at 2~8°C
Transportation: by air or by ocean shipping
LimitNum: 10 Milligram
Plant of Origin: Chinese herbal medicine
Testing Method: NMR/MS/HPLC
Product Ecification: 1mg-1kg
Heavy Metal: <10ppm
Voluntary Standards: company standard
Storage: Store in dry, dark and ventilated plac...
PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.

Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of (-)-Epigallocatechin(EGC)

Cas No.	970-74-1
PubChem ID	72277	Appearance	White-light ochre powder
Formula	C₁₅H₁₄O₇	M.Wt	306.3
Type of Compound	Flavonoids	Storage	Desiccate at -20°C
Synonyms	EGC; Epigallocatechin; l-Epigallocatechin; epi-Gallocatechin
Solubility	DMSO : ≥ 150 mg/mL (489.76 mM) *"≥" means soluble, but saturation unknown.
Chemical Name	(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
SMILES	C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
Standard InChIKey	XMOCLSLCDHWDHP-IUODEOHRSA-N
Standard InChI	InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
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 (-)-Epigallocatechin(EGC)

1 Camellia sp. 2 Casuarina sp. 3 Ephedra sp. 4 Geranium sp. 5 Ginkgo sp. 6 Hippophae sp. 7 Illicium sp. 8 Juniperus sp. 9 Maytenus sp. 10 Phyllanthus sp. 11 Potentilla sp. 12 Primula sp. 13 Rosa sp.

Biological Activity of (-)-Epigallocatechin(EGC)

Description	(-)-Epigallocatechin exhibits antiplatelet,anticoagulation,anti-tumor,anti-cancer and anti-inflammatory functions. Epigallocatechin activates haem oxygenase-1 expression via protein kinase Cdelta and Nrf2. Cu(2+) with (-)-epigallocatechin (EGC) facilitated DNA cleavage, while Ag+ with EGC showed a strong repressive effect.
Targets	LDL \| NO \| HO-1
In vitro	Isolation and characterization of rat intestinal bacteria involved in biotransformation of (-)-epigallocatechin.[Pubmed: 24947740] Arch Microbiol. 2014 Oct;196(10):681-95. Two intestinal bacterial strains MT4s-5 and MT42 involved in the degradation of (-)-Epigallocatechin(EGC) were isolated from rat feces. METHODS AND RESULTS: Strain MT4s-5 was tentatively identified as Adlercreutzia equolifaciens. This strain converted (-)-Epigallocatechin(EGC) into not only 1-(3, 4, 5-trihydroxyphenyl)-3-(2, 4, 6-trihydroxyphenyl)propan-2-ol (1), but also 1-(3, 5-dihydroxyphenyl)-3-(2, 4, 6-trihydroxyphenyl)propan-2-ol (2), and 4'-dehydroxylated (-)-Epigallocatechin(EGC) (7). Type strain (JCM 9979) of Eggerthella lenta was also found to convert (-)-Epigallocatechin(EGC) into 1. Strain MT42 was identified as Flavonifractor plautii and converted 1 into 4-hydroxy-5-(3, 4, 5-trihydroxyphenyl)valeric acid (3) and 5-(3, 4, 5-trihydroxyphenyl)-γ-valerolactone (4) simultaneously. Strain MT42 also converted 2 into 4-hydroxy-5-(3, 5-dihydroxyphenyl)valeric acid (5), and 5-(3, 5-dihydroxyphenyl)-γ-valerolactone (6). Furthermore, F. plautii strains ATCC 29863 and ATCC 49531 were found to catalyze the same reactions as strain MT42. Interestingly, formation of 2 from (-)-Epigallocatechin(EGC) by strain MT4s-5 occurred rapidly in the presence of hydrogen supplied by syntrophic bacteria. Strain JCM 9979 also formed 2 in the presence of the hydrogen or formate. Strain MT4s-5 converted 1, 3, and 4 to 2, 5, and 6, respectively, and the conversion was stimulated by hydrogen, whereas strain JCM 9979 could catalyze the conversion only in the presence of hydrogen or formate. CONCLUSIONS: On the basis of the above results together with previous reports, the principal metabolic pathway of (-)-Epigallocatechin(EGC) and EGCg by catechin-degrading bacteria in gut tract is proposed. Green tea catechins suh α(–)-epicatechin and (–)-epigallocatechin accelerate Cu2+-induced low density lipoprotein in propagation phase[Reference: WebLink] Febs Letters, 1997, 401(2-3):230-234. METHODS AND RESULTS: Effects of (-)-epicatechin (EC) and (-)-Epigallocatechin(EGC) on Cu2+-induced low density lipoprotein (LDL) oxidation were studied in initiation and propagation phases. When 1.5 microM EC or EGC was added to the mixture of isolated human LDL and Cu2+ in the initiation phase, the oxidation of LDL was inhibited in agreement with previous findings. In contrast, in the propagation phase, 1.5 microM of EC or EGC worked as an accelerator of the oxidation, and acceleration ratios (maximum about 6 times) were modified depending on the concentrations of catechin used and the oxidation process in the propagation phase. The evidence was obtained from formation of thiobarbituric acid reactive substances (TBARS), detecting conjugated diene measured by absorbance at 234 nm and investigating fragmentation of apoprotein B (apo B) in LDL. Even in the propagation phase of LDL oxidation, the elevated concentrations of EC or EGC worked as inhibitors: after 40 min incubation of LDL with Cu2+, 10.0 microM EC or 2.0 microM EGC inhibited LDL oxidation. Yet, nitric oxide (NO) released from 5 microM zwitterionic polyamine/NO adducts had an inhibitory in all phases of LDL oxidation. CONCLUSIONS: These results indicate that catechins such as EC and EGC can act as free radical terminators (reducing agents) or accelerators (oxidizing agents) under oxidation circumstances, which is a different character from NO. From the above evidence, further investigations are needed on many natural flavonoids, the most potent antioxidative compounds in foods. DNA cleavage activities of (-)-epigallocatechin, (-)-epicatechin, (+)-catechin, and (-)-epigallocatechin gallate with various kinds of metal ions.[Pubmed: 10610127] Biosci Biotechnol Biochem. 1999 Sep;63(9):1654-6. The DNA cleavage activities of (+)-catechin (C), (-)-epicatechin (EC), (-)-Epigallocatechin(EGC), and (-)-epigallocatechin gallate (EGCg) were examined with 16 different metal ions. Cu(2+) with all the catechins facilitated DNA cleavage, while Ag+ with EGC and EC showed a strong repressive effect. The other metal ions examined showed little effect.
In vivo	Blood anticoagulation and antiplatelet activity of green tea (-)-epigallocatechin (EGC) in mice.[Pubmed: 24056410] Food Funct. 2013 Oct;4(10):1521-5. (-)-Epigallocatechin(EGC) was prepared from green tea polyphenols through column chromatography of a polyamide (3.6 × 40 cm). METHODS AND RESULTS: Three dosages of EGC (0.25, 0.5, 1.0 g kg(-1) d(-1)) were ingested respectively by ICR mice via gavage. Compared with the control group, group (-)-Epigallocatechin(EGC) 0.5 (dosage, 0. 5 g kg(-1) d(-1)) and group (-)-Epigallocatechin(EGC) 1.0 (dosage, 1.0 g kg(-1) d(-1)) presented significant inhibition on platelet aggregation in mice accompanied by 18.4 and 25.6% of inhibition ratio, respectively. The bleeding times (BT) of mice in group (-)-Epigallocatechin(EGC) 0.5 and group EGC1.0 were significantly prolonged (P < 0.01) as well as blood clotting time (BCT) in group (-)-Epigallocatechin(EGC) 1.0 (P < 0.05). All three dosages of EGC prolonged activated partial thromboplastin time (APTT) significantly (P < 0.01), but had no prominent effect on prothrombin time (PT) and fibrinogen level which indicated that the anticoagulation of (-)-Epigallocatechin(EGC) could not be attributed to the level decrease of coagulation factor such as fibrinogen. CONCLUSIONS: The results demonstrated that EGC had prominent antiplatelet activity and blood anticoagulation in a dose-dependent manner.

References on (-)-Epigallocatechin(EGC)

DNA cleavage activities of (-)-epigallocatechin, (-)-epicatechin, (+)-catechin, and (-)-epigallocatechin gallate with various kinds of metal ions.[Pubmed:10610127]

Biosci Biotechnol Biochem. 1999 Sep;63(9):1654-6.

The DNA cleavage activities of (+)-catechin (C), (-)-epicatechin (EC), (-)-epigallocatechin (EGC), and (-)-epigallocatechin gallate (EGCg) were examined with 16 different metal ions. Cu(2+) with all the catechins facilitated DNA cleavage, while Ag+ with EGC and EC showed a strong repressive effect. The other metal ions examined showed little effect.

Isolation and characterization of rat intestinal bacteria involved in biotransformation of (-)-epigallocatechin.[Pubmed:24947740]

Arch Microbiol. 2014 Oct;196(10):681-95.

Two intestinal bacterial strains MT4s-5 and MT42 involved in the degradation of (-)-epigallocatechin (EGC) were isolated from rat feces. Strain MT4s-5 was tentatively identified as Adlercreutzia equolifaciens. This strain converted EGC into not only 1-(3, 4, 5-trihydroxyphenyl)-3-(2, 4, 6-trihydroxyphenyl)propan-2-ol (1), but also 1-(3, 5-dihydroxyphenyl)-3-(2, 4, 6-trihydroxyphenyl)propan-2-ol (2), and 4'-dehydroxylated EGC (7). Type strain (JCM 9979) of Eggerthella lenta was also found to convert EGC into 1. Strain MT42 was identified as Flavonifractor plautii and converted 1 into 4-hydroxy-5-(3, 4, 5-trihydroxyphenyl)valeric acid (3) and 5-(3, 4, 5-trihydroxyphenyl)-gamma-valerolactone (4) simultaneously. Strain MT42 also converted 2 into 4-hydroxy-5-(3, 5-dihydroxyphenyl)valeric acid (5), and 5-(3, 5-dihydroxyphenyl)-gamma-valerolactone (6). Furthermore, F. plautii strains ATCC 29863 and ATCC 49531 were found to catalyze the same reactions as strain MT42. Interestingly, formation of 2 from EGC by strain MT4s-5 occurred rapidly in the presence of hydrogen supplied by syntrophic bacteria. Strain JCM 9979 also formed 2 in the presence of the hydrogen or formate. Strain MT4s-5 converted 1, 3, and 4 to 2, 5, and 6, respectively, and the conversion was stimulated by hydrogen, whereas strain JCM 9979 could catalyze the conversion only in the presence of hydrogen or formate. On the basis of the above results together with previous reports, the principal metabolic pathway of EGC and EGCg by catechin-degrading bacteria in gut tract is proposed.

Blood anticoagulation and antiplatelet activity of green tea (-)-epigallocatechin (EGC) in mice.[Pubmed:24056410]

Food Funct. 2013 Oct;4(10):1521-5.

EGC was prepared from green tea polyphenols through column chromatography of a polyamide (3.6 x 40 cm). Three dosages of EGC (0.25, 0.5, 1.0 g kg(-1) d(-1)) were ingested respectively by ICR mice via gavage. Compared with the control group, group EGC0.5 (dosage, 0. 5 g kg(-1) d(-1)) and group EGC1.0 (dosage, 1.0 g kg(-1) d(-1)) presented significant inhibition on platelet aggregation in mice accompanied by 18.4 and 25.6% of inhibition ratio, respectively. The bleeding times (BT) of mice in group EGC0.5 and group EGC1.0 were significantly prolonged (P < 0.01) as well as blood clotting time (BCT) in group EGC1.0 (P < 0.05). All three dosages of EGC prolonged activated partial thromboplastin time (APTT) significantly (P < 0.01), but had no prominent effect on prothrombin time (PT) and fibrinogen level which indicated that the anticoagulation of EGC could not be attributed to the level decrease of coagulation factor such as fibrinogen. The results demonstrated that EGC had prominent antiplatelet activity and blood anticoagulation in a dose-dependent manner.

Description

(-)-Epigallocatechin (EGC) is the most abundant flavonoid in green tea, can bind to unfolded native polypeptides and prevent conversion to amyloid fibrils.

Keywords:

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