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Merck

G6657

(−)-Gallocatechin

≥98% (HPLC)

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C15H14O7
Número CAS:
3371-27-5
Peso molecular:
306.27
NACRES:
NA.77
PubChem Substance ID:
24895266
UNSPSC Code:
12352205
MDL number:
MFCD01632616

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Nombre del producto

(−)-Gallocatechin, ≥98% (HPLC)

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

SMILES string

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

InChI key

XMOCLSLCDHWDHP-DOMZBBRYSA-N

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

Quality Level

200

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Este artículo
01388G6782C0692
(−)-Gallocatechin ≥98% (HPLC)

Sigma-Aldrich

G6657

(−)-Gallocatechin

(−)-Gallocatechin analytical standard

Supelco

01388

(−)-Gallocatechin

(−)-Gallocatechin gallate from green tea, ≥98% (HPLC)

Sigma-Aldrich

G6782

(−)-Gallocatechin gallate

(−)-Catechin gallate ≥98% (HPLC), from green tea

Sigma-Aldrich

C0692

(−)-Catechin gallate

assay

≥98% (HPLC)

assay

≥97.0% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

food and beverages

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

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

solubility

-

solubility

-

solubility

-

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)[1]
  • 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[2]
  • 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[3]

Biochem/physiol Actions

(−)-Gallocatechin (GC) exerts antioxidant properties by scavenging free radicals.[4] It can also inhibit osteoclastgenesis.[5] GC elicits antimutagenic activity in Escherichia coli against ultraviolet (UV)-induced mutation.[6] It also displays an inhibitory effect on the growth and adherence of Porphyromonas gingivalis in the buccal epithelial cells.[7]

General description

(−)-Gallocatechin is a polyphenolic compound and one of the primary catechins present in green tea Camellia sinensis.[8]

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000453797
0000453797
0000442599
0000442598
0000442598

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S Sakanaka et al.
Bioscience, biotechnology, and biochemistry, 60(5), 745-749 (1996-05-01)
Effects of polyphenolic compounds isolated from green tea (Camellia sinensis) on the growth and adherence of Porphyromonas gingivalis onto human buccal epithelial cells were investigated. Green tea polyphenols, especially (-)-epigallocatechin gallate (EGCg) which is a dominant component of tea polyphenols
G W Plumb et al.
Redox report : communications in free radical research, 7(1), 41-46 (2002-05-01)
Gallocatechins and a range of prodelphinidins were purified by high performance liquid chromatography from pomegranate peel. Gallocatechin, gallocatechin-(4-8)-catechin, gallocatechin-(4-8)-gallocatechin and catechin-(4-8)-gallocatechin were all identified, purified and quantified by LC-DAD-MS and MS-MS. The antioxidant properties of these compounds were assessed using
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)
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
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