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G6657

(−)-Gallocatechin

≥98% (HPLC)

Synonym(s):

(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol

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About This Item

Empirical Formula (Hill Notation):
C15H14O7
CAS Number:
3371-27-5
Molecular Weight:
306.27
NACRES:
NA.77
PubChem Substance ID:
24895266
UNSPSC Code:
12352205
MDL number:
MFCD01632616
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Quality Level

200

assay

≥98% (HPLC)

solubility

H2O: 5 mg/mL (heat 2-10 min at 105C), alcohol: soluble

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

O[C@@H]1Cc2c(O)cc(O)cc2O[C@H]1c3cc(O)c(O)c(O)c3

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

InChI key

XMOCLSLCDHWDHP-DOMZBBRYSA-N

General description

(−)-Gallocatechin is a polyphenolic compound and one of the primary catechins present in green tea Camellia sinensis.

Application

(−)-Gallocatechin has been used as a reference standard:
  • for the identification of phenolic compounds present in Pineapple (Ananas comosus) using high-performance liquid chromatography (HPLC)
  • to evaluate the catechin profiles from Camellia sinensis green tea, white tea, and flower sample by high-performance liquid chromatography/photodiode array detection (RP-HPLC/PDAD) analysis
  • as a reference standard for the flavan-3-ols profiling muscadine grape hybrid varieties using high-performance liquid chromatography-quadrupole, time-of-flight, tandem mass spectrometry (HPLC-qTOF-MS/MS) analysis

Biochem/physiol Actions

(−)-Gallocatechin (GC) exerts antioxidant properties by scavenging free radicals. It can also inhibit osteoclastgenesis. GC elicits antimutagenic activity in Escherichia coli against ultraviolet (UV)-induced mutation. It also displays an inhibitory effect on the growth and adherence of Porphyromonas gingivalis in the buccal epithelial cells.

Other Notes

Polyphenolic compound found in green tea. An epimer of (−)-epigallocatechin.

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000453797
0000453797
0000442599
0000442598
0000442599

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Simultaneous analysis of individual catechins and caffeine in green tea
Goto T, et al.,
Journal of Chromatography A, 295-299 (1996)
Chun Hay Ko et al.
Journal of agricultural and food chemistry, 57(16), 7293-7297 (2009-08-06)
In this study, three tea catechins, epigallocatechin (EGC), gallocatechin (GC), and gallocatechin gallate (GCG), were investigated for their effects on bone metabolism. The effects of the tea catechins on bone formation were evaluated using cultured rat osteoblast-like osteosarcoma cell line
Q Guo et al.
Biochimica et biophysica acta, 1427(1), 13-23 (1999-03-20)
The purpose of this study is to examine the relationship between the free radical scavenging activities and the chemical structures of tea catechins ((-)-epigallocatechin gallate (EGCG), (-)-epigallocatechin (EGC) and (-)-epicatechin (EC)) and their corresponding epimers ((-)-gallocatechin gallate (GCG), (-)-gallocatechin (GC)
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