MilliporeSigma
All Photos(3)

Documents

G6657

Sigma-Aldrich

(−)-Gallocatechin

≥98% (HPLC)

Sign Into View Organizational & Contract Pricing

Synonym(s):
(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
Empirical Formula (Hill Notation):
C15H14O7
CAS Number:
Molecular Weight:
306.27
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
G6782C0692E4268
vibrant-m

G6657

(−)-Gallocatechin

vibrant-m

G6782

(−)-Gallocatechin gallate

vibrant-m

C0692

(−)-Catechin gallate

vibrant-m

E4268

(−)-Epigallocatechin gallate

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

Quality Level

200

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

-

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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 9

1 of 9

(−)-Epicatechin ≥90% (HPLC)

Sigma-Aldrich

E1753

(−)-Epicatechin

(+)-Catechin analytical standard

Supelco

43412

(+)-Catechin

(−)-Catechin 3-gallate phyproof® Reference Substance

PHL82497

(−)-Catechin 3-gallate

Epigallocatechin primary reference standard

03960590

Epigallocatechin

(−)-Gallocatechin gallate analytical standard

Supelco

80352

(−)-Gallocatechin gallate

(−)-Epicatechin analytical standard

Supelco

68097

(−)-Epicatechin

(+)-Catechin hydrate ≥98% (HPLC), powder

Sigma-Aldrich

C1251

(+)-Catechin hydrate

(+)-Catechin phyproof® Reference Substance

PHL89172

(+)-Catechin

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
Simultaneous analysis of individual catechins and caffeine in green tea
Goto T, et al.,
Journal of Chromatography A, 295-299 (1996)
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
T Matsuo et al.
Phytochemistry, 36(4), 1027-1029 (1994-07-01)
From the MeOH-extract of guava leaves, (+)-gallocatechin was isolated as a bio-antimutagenic compound against UV-induced mutation in Escherichia coli. This strengthens the evidence that phenolic compounds require three neighbouring-OH groups in order to possess this activity.
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

Articles

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Related Content

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service