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(-)-Gallocatechin

CAS# 3371-27-5

(-)-Gallocatechin

Catalog No. BCN5927----Order now to get a substantial discount!

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Chemical structure

(-)-Gallocatechin

3D structure

Chemical Properties of (-)-Gallocatechin

Cas No. 3371-27-5 SDF Download SDF
PubChem ID 9882981 Appearance White powder
Formula C15H14O7 M.Wt 306.27
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms GC
Solubility Soluble in ethanol and methan
Chemical Name (2S,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-DOMZBBRYSA-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 (-)-Gallocatechin

1 Agrimonia sp. 2 Camellia sp. 3 Castanea sp. 4 Casuarina sp. 5 Ceratonia sp. 6 Croton sp. 7 Ephedra sp. 8 Fragaria sp. 9 Geranium sp. 10 Hamamelis sp. 11 Juniperus sp. 12 Malus sp. 13 Phyllanthus sp. 14 Potentilla sp. 15 Quercus sp. 16 Rheum sp. 17 Rhus sp. 18 Rosa sp.

Biological Activity of (-)-Gallocatechin

Description(-)-Epigallocatechin has been shown to exhibit antioxidant, anti-cancer and anti-inflammatory functions.
TargetsROS
In vitro

Antioxidant Potential of Gallocatechins. A Pulse Radiolysis and Laser Photolysis Study[Reference: WebLink]

J. Am. Chem. Soc., 1995, 117(39):9881-8.

Gallocatechins and catechins, which are constituents of green tea, and related, simpler single-ring model compounds undergo one-electron oxidation by the azidyl radical (k = (1.4-4.8) x 10(9) M(-1) s(-1)), which was used as a model one-electron, rapid oxidant.
METHODS AND RESULTS:
The initial oxidation leads to the formation of a mixture of A- and B- (or C-) ring phenoxyl radicals. This finding was confirmed by comparison with the spectra of 3,5-dihydroxyanisole (the model for A ring) and methyl gallate (the model for B or C ring) radicals and by photoionization experiments in which only the B-ring radical of epigallocatechin was generated, as expected from its lower ionization potential. The A-ring phenoxyl radical is converted to the B- (or C-) ring phenoxyl radical by inter- and intramolecular electron and proton transfer. The activation parameters clearly indicate solvent-assisted intermolecular electron and proton transfer, whereas intramolecular transfer in epigallocatechin gallate radicals is suggested to proceed through an intermediate molecular complex formation. Acid-base equilibria of parent gallocatechins (pK(al) > 8.0) are significantly altered in the corresponding phenoxyl radicals (pK(rl) = 4.4-5.5). The low reduction potentials of gallocatechin radicals, E(7) = 0.42 V (which is lower than that of vitamin E radicals, E(7) = 0.48 V), are responsible for their antioxidant efficacy, which may include the repair of vitamin E radicals. These low reduction potentials also imply high susceptibility of parent gallocatechins to rapid oxidation in aerated aqueous media. The reactivity of epigallocatechin gallate with superoxide radical at pH 7, k = 7.3 x 10(5) M(-1) s(-1) is one of the highest measured rates of reduction of superoxide radical by any chemical antioxidant. In this reaction, superoxide is converted to hydrogen peroxide, thus eliminating the redox cycling that may be involved in the corresponding oxidation reaction.
CONCLUSIONS:
The high rates of quenching of singlet oxygen by gallocatechins in acetonitrile, k = (1.1-2.2) x 10(8) M(-1) s(-1), are comparable to quenching by vitamin E, k = 5 x 10(8) M(-1) s(-1).

Protocol of (-)-Gallocatechin

Structure Identification
Biol Pharm Bull. 2015;38(2):325-30.

Biotransformation of (-)-epigallocatechin and (-)-gallocatechin by intestinal bacteria involved in isoflavone metabolism.[Pubmed: 25747993]

Four isoflavone-metabolizing bacteria were tested for their abilities to degrade (-)-epigallocatechin (EGC) and its isomer (-)-Gallocatechin (GC).
METHODS AND RESULTS:
Biotransformation of both EGC and GC was observed with Adlercreutzia equolifaciens JCM 14793, Asaccharobacter celatus JCM 14811, and Slackia equolifaciens JCM 16059, but not Slackia isoflavoniconvertens JCM 16137. With respect to the degradation of EGC, strain JCM 14793 only catalyzed 4'-dehydroxylation to produce 4'-dehydroxylated EGC (7). Strain JCM 14811 mainly produced 7, along with a slight formation of the C ring-cleaving product 1-(3,4,5-trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol (1). Strain JCM 16059 catalyzed only C ring cleavage to form 1. Interestingly, the presence of hydrogen promoted the bioconversion of EGC by these bacteria. In addition, strain JCM 14811 revealed the ability to catalyze 4'-dehydroxylation of 1 to yield 1-(3,5-dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol (2) in the presence of hydrogen. In the case of GC, strain JCM 14793 mainly produced C ring-cleaving product (1) with only a very small amount of 4'-dehydroxylated GC (8), while Strain JCM 14811 only catalyzed 4'-dehydroxylation to form 8. Strain JCM 16059 formed 1. The bioconversion of GC by the three strains was stimulated by hydrogen. Strain JCM 14793 showed the ability to convert 1 into 2 in the presence of hydrogen as did strain JCM 14811. Furthermore, strains JCM 14793 and JCM 14811 were found to have the ability to catalyze p-dehydroxylation of the pyrogallol moiety in the EGC metabolites 4-hydroxy-5-(3,4,5-trihydroxyphenyl)valeric acid (3) and 5-(3,4,5-trihydroxyphenyl)-γ-valerolactone (4), and this ability was enhanced by the presence of hydrogen.

(-)-Gallocatechin Dilution Calculator

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(-)-Gallocatechin Molarity Calculator

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Preparing Stock Solutions of (-)-Gallocatechin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2651 mL 16.3255 mL 32.6509 mL 65.3019 mL 81.6273 mL
5 mM 0.653 mL 3.2651 mL 6.5302 mL 13.0604 mL 16.3255 mL
10 mM 0.3265 mL 1.6325 mL 3.2651 mL 6.5302 mL 8.1627 mL
50 mM 0.0653 mL 0.3265 mL 0.653 mL 1.306 mL 1.6325 mL
100 mM 0.0327 mL 0.1633 mL 0.3265 mL 0.653 mL 0.8163 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 (-)-Gallocatechin

Biotransformation of (-)-epigallocatechin and (-)-gallocatechin by intestinal bacteria involved in isoflavone metabolism.[Pubmed:25747993]

Biol Pharm Bull. 2015;38(2):325-30.

Four isoflavone-metabolizing bacteria were tested for their abilities to degrade (-)-epigallocatechin (EGC) and its isomer (-)-Gallocatechin (GC). Biotransformation of both EGC and GC was observed with Adlercreutzia equolifaciens JCM 14793, Asaccharobacter celatus JCM 14811, and Slackia equolifaciens JCM 16059, but not Slackia isoflavoniconvertens JCM 16137. With respect to the degradation of EGC, strain JCM 14793 only catalyzed 4'-dehydroxylation to produce 4'-dehydroxylated EGC (7). Strain JCM 14811 mainly produced 7, along with a slight formation of the C ring-cleaving product 1-(3,4,5-trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol (1). Strain JCM 16059 catalyzed only C ring cleavage to form 1. Interestingly, the presence of hydrogen promoted the bioconversion of EGC by these bacteria. In addition, strain JCM 14811 revealed the ability to catalyze 4'-dehydroxylation of 1 to yield 1-(3,5-dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol (2) in the presence of hydrogen. In the case of GC, strain JCM 14793 mainly produced C ring-cleaving product (1) with only a very small amount of 4'-dehydroxylated GC (8), while Strain JCM 14811 only catalyzed 4'-dehydroxylation to form 8. Strain JCM 16059 formed 1. The bioconversion of GC by the three strains was stimulated by hydrogen. Strain JCM 14793 showed the ability to convert 1 into 2 in the presence of hydrogen as did strain JCM 14811. Furthermore, strains JCM 14793 and JCM 14811 were found to have the ability to catalyze p-dehydroxylation of the pyrogallol moiety in the EGC metabolites 4-hydroxy-5-(3,4,5-trihydroxyphenyl)valeric acid (3) and 5-(3,4,5-trihydroxyphenyl)-gamma-valerolactone (4), and this ability was enhanced by the presence of hydrogen.

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