Natural flavonoid in green tea; COX-1/cyclooxygenase-1
2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol targets multiple molecular pathways involved in oxidative stress, inflammation, and cell survival. It exerts antioxidant activity by scavenging reactive oxygen species and enhancing the activity of antioxidant enzymes. The compound's flavonoid structure allows it to interact with various signaling pathways including those involved in cancer, diabetes, and cardiovascular protection. Its effects are mediated through modulation of redox-sensitive transcription factors and enzyme activities.

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].

---

In vitro, 2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol exhibits potent antioxidant activity, scavenging reactive oxygen species and enhancing the activity of antioxidant enzymes. It shows anticancer, anti-obesity, antidiabetic, cardiovascular protective, anti-infectious, hepatoprotective, and neuroprotective effects in various cell-based assays. These activities are attributed to its ability to modulate multiple signaling pathways through its antioxidant and polyphenolic properties. Specific IC50 values are not detailed in the available literature.

In vivo, 2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol (catechin) has been extensively studied as a dietary polyphenol. Catechin and related flavan-3-ols have demonstrated beneficial effects in animal models of cancer, diabetes, obesity, cardiovascular disease, and neurodegeneration. These effects are mediated through antioxidant, anti-inflammatory, and metabolic regulatory mechanisms. However, specific published in vivo protocols for this particular compound are not detailed in the available literature, and studies would follow standard protocols for catechin and related flavonoids.

The antioxidant activity is assessed using various in vitro assays. DPPH radical scavenging, ABTS cation radical scavenging, and FRAP (ferric reducing antioxidant power) assays are commonly used to measure the compound's free radical scavenging capacity. Cellular antioxidant activity is assessed in cell cultures by measuring intracellular ROS levels using DCFH-DA after treatment with the compound and exposure to oxidative stress inducers such as H₂O₂. The activity of antioxidant enzymes (e.g., SOD, CAT, GPx) may also be measured in cell lysates.

For cellular studies, various cell lines including cancer cells, hepatocytes, neuronal cells, and adipocytes are cultured in appropriate media. Cells are treated with 2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol at various concentrations for 24-72 hours. Cell viability is assessed using MTT or similar assays. Apoptosis is evaluated by flow cytometry. ROS levels are measured using DCFH-DA. Protein expression of antioxidant enzymes, inflammatory markers, and signaling proteins is analyzed by Western blot. Glucose uptake and lipid accumulation may also be assessed in relevant cell models.

In vivo studies for catechin and related flavan-3-ols are conducted in various animal models. For anticancer studies, xenograft models are used. For diabetes and obesity studies, high-fat diet-induced or streptozotocin-induced diabetic models are employed. For cardiovascular studies, models of atherosclerosis or hypertension are used. For neuroprotection studies, models of neurodegeneration (e.g., MPTP, 6-OHDA, or Aβ-induced toxicity) are employed. The compound is typically administered via oral gavage or in the diet, and endpoints vary depending on the disease model.

Catechin and related flavonoids are known to have variable oral bioavailability due to extensive metabolism in the gastrointestinal tract and liver. The compound is subject to conjugation (glucuronidation, sulfation) and methylation, which affect its systemic exposure. Pharmacokinetic studies in animal models show that catechin reaches peak plasma concentrations within 1-2 hours after oral administration, with a half-life of several hours. However, specific PK data for 2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol are not detailed in the available literature.

Catechin and related flavan-3-ols are generally considered safe and are widely consumed in the human diet (e.g., in tea, cocoa, and fruits). At typical dietary intake levels, no significant toxicity is observed. However, at high doses used in research, potential adverse effects may include hepatotoxicity or gastrointestinal disturbances. Comprehensive toxicology studies have been conducted for catechin as a dietary supplement, but specific data for 2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol are limited.

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

(+)-Catechin is the (+)-enantiomer of catechin and is a polyphenolic antioxidant plant metabolite. It has dual functions of antioxidation and plant metabolism. It is the enantiomer of (-)-catechin. An antioxidant flavonoid compound, mainly found in woody plants, exists in both (+)-catechin and (-)-epicatechin (cis) forms. It has been reported that anthocyanin alcohols are found in tea (Camellia sinensis), peony (Paeonia obovata), and other organisms with relevant data. Catechins are metabolites found or produced in Saccharomyces cerevisiae. An antioxidant flavonoid compound, mainly found in woody plants, exists in both (+)-catechin and (-)-epicatechin (cis) forms. See also: gallic catechin (with subclasses); Kroefeller (monomer). Blueberry (partial)...

---

Tea, a product made from the leaves and buds of the tea plant (Camellia sinensis), is one of the richest sources of catechins, with its main catechin component being (−)-epigallocatechin-3-gallate (EGCG) (Figure 1). EGCG has numerous health benefits, such as anti-cancer, anti-obesity, anti-diabetic, anti-cardiovascular disease, anti-infection, hepatoprotective, and neuroprotective effects. Numerous human epidemiological and clinical studies on tea have confirmed its anti-cancer efficacy, supported by cell and animal experiments, although some studies have reported conflicting results. Furthermore, detailed molecular mechanisms of action of EGCG and other catechins have been proposed. One of the most intriguing mechanisms involves reactive oxygen species (ROS). EGCG is known to have a dual role with respect to ROS, acting as both an antioxidant and a pro-oxidant. Multiple pieces of evidence suggest that EGCG can both eliminate ROS by scavenging them and promote their production.
Regarding the anticancer effects of green tea catechins, Shirakami and Shimizu provided updated information on their various mechanisms, including antioxidant, pro-oxidative and anti-inflammatory activities, immune and epigenetic modifications, and receptor tyrosine kinase inhibition. They noted that due to the low bioavailability of EGCG, it is currently unclear whether observations of high concentrations of EGCG in vitro can be directly extrapolated to cancer chemoprevention in animals and humans. [1]

---

2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol ((±)-Catechin) is a flavan-3-ol flavonoid with potent antioxidant, anticancer, antidiabetic, cardiovascular protective, and neuroprotective effects. It scavenges ROS and enhances antioxidant enzyme activity. Widely consumed in the diet, it is used in research on oxidative stress and chronic diseases. No clinical trials or approvals exist for therapeutic use. For research use only.

C15H14O6

290.26806

308.089

7295-85-4

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

9064

White to off-white solid powder

214 °C

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.

---

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).

View More

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)

---

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).

View More

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

---

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.

---

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