3371-27-5

Basic information

• Product Name: (-)-GALLOCATECHIN
• Synonyms: [2S,3R]-2-[3,4,5-TRIHYDROXYPHENYL]-3,4-DIHYDRO-1[2H]-BENZOPYRAN-3,5,7-TRIOL;(-)-GALLOCATECHIN;GALLOCATECHIN;(-)-GC;GALLOCATECHIN, (-)-(SH);()-Gallocatechin,(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol;(2S,3R)-3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol;(2S-trans)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
• CAS NO: 3371-27-5
• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.27
• Product Categories: Miscellaneous Natural Products;Catechins & Tannins;Aromatics;Heterocycles;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 3371-27-5.mol

Chemical Properties

• Melting Point: 200℃
• Boiling Point: 685.63 °C at 760 mmHg
• Flash Point: 368.456 °C
• Appearance: /
• Density: 1.696 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.776
• Storage Temp.: 2-8°C
• Solubility: H2O: 5 mg/mL with brief sonication
• PKA: 9.02±0.15(Predicted)
• CAS DataBase Reference: (-)-GALLOCATECHIN(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-GALLOCATECHIN(3371-27-5)
• EPA Substance Registry System: (-)-GALLOCATECHIN(3371-27-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3371-27-5(Hazardous Substances Data)

Usage

Uses

Used in Antioxidant Applications:
(-)-Gallocatechin is used as an antioxidant for its free radical scavenging ability, which helps in protecting cells from damage caused by reactive oxygen species.
Used in Cancer Chemoprevention:
(-)-Gallocatechin is used as a potential cancer chemopreventive agent due to its anti-tumorigenic properties, which may help in preventing the development of cancer.
Used in Dental Applications:
(-)-Gallocatechin is used as an agent to inhibit the growth and adherence of P. gingivalis onto the buccal epithelial cells, which can help in preventing periodontal diseases.
Used in Analytical Chemistry:
(-)-Gallocatechin is used as a reference standard for the identification of phenolic compounds present in various sources such as pineapple (Ananas comosus) using high-performance liquid chromatography (HPLC), and for evaluating the catechin profiles from Camellia sinensis green tea, white tea, and flower samples by high-performance liquid chromatography/photodiode array detection (RP-HPLC/PDAD) analysis.
Used in Food Industry:
(-)-Gallocatechin is used as a reference standard for the flavan-3-ols profiling in muscadine grape hybrid varieties using high-performance liquid chromatography-quadrupole, time-of-flight, tandem mass spectrometry (HPLC-qTOF-MS/MS) analysis, which helps in the quality assessment and authentication of grape products.

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.

InChI:InChI=1/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

Upstream product

• 89013-67-2 (-)-epigallocatechin 3,4'-di-O-gallate 
• 89013-66-1 (-)-epigallocatechin 3,3'-di-O-gallate 
• 2596-50-1 (-)-epigallocathechin gallate 
• 332386-74-0 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol 
• 1333874-50-2 7-O-(β-Glcp-6-O-galloyl)-(+)-catechin-(4α->8)-(+)-catechin-(4α->8)-(-)-epigallocatechin 
• 108-98-5 thiophenol 
• 1449477-34-2 C₂₄H₃₆O₉ 
• 1449477-27-3 C₂₄H₃₄O₈ 
• 1449477-26-2 C₄₄H₅₀O₁₀ 
• 1449477-38-6 C₄₄H₄₈O₁₀ 
• 1449477-36-4 C₄₄H₅₀O₁₀ 
• 1449477-39-7 C₃₀H₃₈O₁₀ 
• 1449477-37-5 C₃₀H₃₈O₁₀ 
• 135820-76-7 gallocatechin-(4α->8)-gallocatechin-(4α->8)-epigallocatechin 

Downstream Products

• 3371-27-5 (-)-gallocatechin 
• 4670-05-7 theaflavin 
• 302776-47-2 theanaphthoquinone 
• 979-92-0 S-(5'-adenosyl)-L-homocysteine 

Relevant articles and documents

Oxidation and epimerization of epigallocatechin in banana fruits

To examine the metabolism of proanthocyanidins in banana fruit, (-)- epigallocatechin was treated with the homogenate of the fruit flesh to yield (-)-gallocatechin and an oxidation product, 1-(3,4,5-trihydroxyphenyl)-3- (2,4,6-trihydroxyphenyl)-2-hydroxy-

A new mechanism for oxidation of epigallocatechin and production of benzotropolone pigments

Enzymatic oxidation of (-)-epigallocatechin gave two new quinone dimers, dehydrotheasinensin C and proepitheaflagallin. Dehydrotheasinensin C has a hydrated cyclohexenetrione structure and its oxidation-reduction dismutation reaction yielded black tea pol

Enzymatic oxidation of gallocatechin and epigallocatechin: Effects of C-ring configuration on the reaction products

Tea leaf is rich in pyrogallol-type catechins, and their oxidation is important in the generation of black tea polyphenols. In the present study, the enzymatic oxidation of three pyrogallol-type catechins, (+)- and (-)-gallocatechins and (-)-epigallocatechin, was compared. The reactions yielded unstable quinone products, which were trapped as condensation products with o-phenylenediamine. The oxidation of (+)-gallocatechin proceeded very slowly compared to the reaction of (-)-epigallocatechin, and yielded a proepitheaflagallin-type dimer as the major product, though oxidation of (-)-epigallocatechin gave predominantly dehydrotheasinensin C. The cis-configuration of the C-3 hydroxyl group and the B-ring of (-)-epigallocatechin was apparently crucial for rapid and selective production of dehydrotheasinensin C. Oxidation of (-)-gallocatechin proceeded in a manner similar to that of (+)-gallocatechin, and produced an enantiomer of the (+)-gallocatechin product. The results suggest that enzymes catalyze oxidation of the pyrogallol B-ring to the o-quinone, with subsequent non-enzymatic coupling reactions proceed under highly steric control.

Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols

N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant

Mechanism of oolongtheanin formation via three intermediates

To clarify the mechanism of oolongtheanin formation, the oxidations of (?)-epigallocatechin and (?)-epigallocatechin gallate were investigated, and key intermediates were isolated. These intermediates were determined to be dehydrotheasinensins and pro-oolongtheanins, which we have reported previously, and one novel intermediate. Based on the chemical structures of these intermediates, a mechanism was proposed for oolongtheanin formation from catechins, and confirmed by NMR and GC–MS analysis.

Metabolic characterization of the anthocyanidin reductase pathway involved in the biosynthesis of flavan-3-ols in elite Shuchazao tea (Camellia sinensis) cultivar in the field

Anthocyanidin reductase (ANR) is a key enzyme in the ANR biosynthetic pathway of flavan-3-ols and proanthocyanidins (PAs) in plants. Herein, we report characterization of the ANR pathway of flavan-3-ols in Shuchazao tea (Camellia sinesis), which is an elite and widely grown cultivar in China and is rich in flavan-3-ols providing with high nutritional value to human health. In our study, metabolic profiling was preformed to identify two conjugates and four aglycones of flavan-3-ols: (-)-epigallocatechin-gallate [(-)-EGCG], (-)-epicatechin-gallate [(-)-ECG], (-)-epigallocatechin [(-)-EGC], (-)-epicatechin [(-)-EC], (+)-catechin [(+)-Ca], and (+)-gallocatechin [(+)-GC], of which (-)-EGCG, (-)-ECG, (-)-EGC, and (-)-EC accounted for 70-85% of total flavan-3-ols in different tissues. Crude ANR enzyme was extracted from young leaves. Enzymatic assays showed that crude ANR extracts catalyzed cyanidin and delphinidin to (-)-EC and (-)-Ca and (-)-EGC and (-)-GC, respectively, in which (-)-EC and (-)-EGC were major products. Moreover, two ANR cDNAs were cloned from leaves, namely CssANRa and CssANRb. His-Tag fused recombinant CssANRa and CssANRb converted cyanidin and delphinidin to (-)-EC and (-)-Ca and (-)-EGC and (-)-GC, respectively. In addition, (+)-EC was observed from the catalysis of recombinant CssANRa and CssANRb. Further overexpression of the two genes in tobacco led to the formation of PAs in flowers and the reduction of anthocyanins. Taken together, these data indicate that the majority of leaf flavan-3-ols in Shuchazao's leaves were produced from the ANR pathway.

Enantioselective total syntheses of (+)-gallocatechin, (-)- epigallocatechin, and 8-C-ascorbyl-(-)-epigallocatechin

Reading the tea leaves: The enatioselective total syntheses of 8-C-ascorbyl-(-)-epigallocatechin was accomplished by CuII-mediated oxidative coupling of ascorbic acid and (-)-epigallocatechin as a key step. Also, the asymmetric total syntheses of tea-leaf extracts (+)-gallocatechin and (-)-epigallocatechin were achieved by Au-catalyzed intramolecular cycliarylation of the precursor epoxide and Sharpless dihydroxylation. Copyright

Isolation of two new bioactive proanthocyanidins from Cistus salvifolius herb extract

Two new proanthocyanidins, epigallocatechin-3-O-p-hydroxybenzoate- (4β→8)-epigallocatechin (1) and epigallocatechin-3-O-p- hydroxybenzoate-(4β→8)-epigallocatechin-3-O-gallate (2) in addition to the known compound epigallocatechin-(4β→6)-epigallocatechin-3-O- gallate (3), were isolated from the air-dried herb of Cistus salvifolius. The chemical structures were determined on the basis of 1D-and 2D-NMR-spectra (HSQC, HMBC) of their peracetylated derivatives, MALDI-TOF-mass spectra, and by acid-catalysed degradation with phloroglucinol. The isolated compounds 1-3 and the water extract of C. salvifolius herb were tested for their inhibitory activities against COX-1 and COX-2. Compound 2 showed the strongest inhibitory effect on COX-2 followed by compound 3, compound 1 and the water extract, while compounds 1-3 exhibited moderate in vitro inhibition against COX-1.

New oligomeric proanthocyanidins from Alhagi pseudalhagi

Two new oligomeric proanthocyanidin glucosides were isolated from the aerial part and roots of Alhagi pseudalhagi. Their structures and relative configurations were elucidated as 7-O-β-D-Glc p→6 galloyl-(+)catechin-(4α-8)-(+)-catechin-(4α-8)-(-

General synthesis of epi-series catechins and their 3-gallates: Reverse polarity strategy

A general synthetic route to the epi-series catechins was developed based on the reverse polarity strategy. Aromatic nucleophilic substitution reaction followed by the sulfinyl-metal exchange and cyclization enabled stereo-controlled access to various members of epi-series catechins and their 3-gallates.