(-)-Gallocatechin gallate

Names

[ Name ]:
(-)-Gallocatechin gallate

[Synonym ]:
Benzoic acid, 3,4,5-trihydroxy-, (2S,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
(−)-Gallocatechin gallate
(-)-Gallocatechin gallate
(2S,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
Gallocatechin gallate
MFCD00214298
GCG
[(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
(-)-Gallocatechin 3-O-gallate

Biological Activity

[Description]:

(-)-Gallocatechin gallate is the polyphenol isolated from tea, with cancer-preventive activities.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Flavonoids

[In Vitro]

The amount of (-)-Gallocatechin gallate does not differ in leaves of different stages, and the content is relatively low[1]. (−)-gallocatechin gallate in combination with active catechins ((−)-epigallocatechin gallate) has synergistic effects on the induction of apoptosis and inhibition of cell growth for PC-9 cells. (−)-gallocatechin gallate shows inhibitory effect on α-Glucosidase and DPPH, with IC50s of 30.2 μM and 12.2 μg/mL[2].

[Cell Assay]

Cell viability is examined by measuring the capability of cells to metabolize MTT to a purple formazan dye. Human liver cancer HepG2 cells are maintained in DMEM medium supplemented with 10% fetal bovine serum, 100 units/mL penicillin, and 50 units/mL streptomycin at 37°C in a humidified incubator with 5% CO2 atmosphere. Cells are seeded in 96-well tissue culture plates for 24 h and then incubated with the tested compounds at different concentrations for 72 h. After incubation, 25 μL MTT in 5 mg/mL PBS is added and incubated for 4 h. The medium is aspirated and replaced with 150 μL dimethyl sulfoxide (DMSO) to dissolve the formazan salt. The color intensity of the formazan solution, which reflects the cell growth condition, is measured at 570 nm using a microplate spectrophotometer.

[References]

[1]. Zhang LQ, et al. Accumulation of catechins and expression of catechin synthetic genes in Camellia sinensis at different developmental stages. Bot Stud. 2016 Dec;57(1):31.

[2]. Zhou H, et al. C-geranylated flavanones from YingDe black tea and their antioxidant and α-glucosidase inhibition activities. Food Chem. 2017 Nov 15;235:227-233.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
909.1±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₂H₁₈O₁₁

[ Molecular Weight ]:
458.372

[ Flash Point ]:
320.0±27.8 °C

[ Exact Mass ]:
458.084900

[ PSA ]:
197.37000

[ LogP ]:
2.08

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.857

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH9000000

CHEMICAL NAME :: Benzoic acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)- 2H-1-benzopyran-3-yl ester, (2S-trans)-

CAS REGISTRY NUMBER :: 4233-96-9

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H18-O11

MOLECULAR WEIGHT :: 458.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #93-944

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DH9000000

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