Natural flavonoid in green tea; COX-1/cyclooxygenase-1

Catechin, the name of which is derived from catechu of the extract of Acacia catechu L., is 3,3’,4’,5,7-pentahydroxyflavan with two steric forms of (+)-catechin (Figure 1) and its enantiomer. In addition, in a broad sense, catechin represents the chemical family name of the compounds derived from catechin. Catechins are distributed in a variety of foods and herbs including tea, apples, persimmons, cacaos, grapes, and berries. This special issue is devoted to information on catechin’s activities related to human health[1].

[1]. Mamoru Isemura. Catechin in Human Health and Disease. Molecules. 2019 Feb 1;24(3):528.

(+)-catechin is the (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. It has a role as an antioxidant and a plant metabolite. It is an enantiomer of a (-)-catechin.
An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.
Cianidanol has been reported in Camellia sinensis, Paeonia obovata, and other organisms with data available.
Catechin is a metabolite found in or produced by Saccharomyces cerevisiae.
An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.
See also: Gallocatechin (has subclass); Crofelemer (monomer of); Bilberry (part of) ...

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Tea, a product obtained from the leaves and buds of the plant Camellia sinensis, is one of the richest catechin sources and contains, as the major catechin, (−)-epigallocatechin-3-gallate (EGCG) (Figure 1) which has many beneficial properties for human health such as anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects. A number of human epidemiological and clinical studies on tea have provided evidence for its anticancer benefits and these results have been supported by cell-based and animal experiments, although studies that show conflicting results have also been reported. In addition, detailed molecular mechanisms have been proposed for the action mechanism of EGCG and other catechins. One of the most attractive mechanisms is the one in which reactive oxygen species (ROS) is involved. EGCG is known to have dual actions in relation to ROS as an anti-oxidant and a pro-oxidant. Several lines of evidence have indicated that EGCG can both eliminate ROS by scavenging and enhance ROS production.
With respect to the anticancer effect of green tea catechins, Shirakami and Shimizu provided updated information on diverse mechanisms, including anti-oxidative, pro-oxidative, and anti-inflammatory activities, immune and epigenetic modification, and receptor tyrosine kinase inhibition. They pointed out that it is unclear whether the in vitro observation with high concentrations of EGCG can be directly extrapolated to cancer chemoprevention in animals and humans because of its low bioavailability.[1]

C15H14O6

290.26806

308.089

7295-85-4

(+)-Catechin hydrate;225937-10-0;Catechin;154-23-4

9064

White to off-white solid powder

~200 °C (dec.)

1.481

5

6

1

21

364

2

C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

PFTAWBLQPZVEMU-DZGCQCFKSA-N

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1

(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol; L-Epicatechin; 13392-26-2; 7295-85-4; (+/-)-Catechin; (+/-)-Epicatechin; 17334-50-8; CHEBI:23053;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~125 mg/mL (~430.63 mM)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)