| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg | |||
| Other Sizes |
| Targets |
As a flavonoid, 2-Hydroxynaringenin does not target a single specific receptor but exerts its biological effects through multiple mechanisms characteristic of polyphenolic compounds. These include: (1) Direct free radical scavenging (antioxidant activity), (2) Modulation of signaling pathways involved in inflammation (e.g., NF-kappaB, MAPK pathways), (3) Regulation of enzymes such as cyclooxygenases (COX), lipoxygenases (LOX), and inducible nitric oxide synthase (iNOS), (4) Interaction with various cellular proteins and modulation of gene expression. The additional hydroxyl group (compared to naringenin) may enhance its antioxidant potency.
|
|---|---|
| ln Vitro |
In vitro, 2-Hydroxynaringenin is a flavonoid with documented antioxidant and anti-inflammatory properties. Based on studies with other hydroxylated flavonoids, it would be expected to scavenge free radicals (including DPPH, ABTS, and superoxide radicals) and reduce oxidative stress in cell-based models. It may also suppress the production of pro-inflammatory mediators (such as TNF-alpha, IL-1beta, IL-6, PGE2, and nitric oxide) in activated macrophages (e.g., LPS-stimulated RAW 264.7 cells) by inhibiting the NF-kappaB and MAPK signaling pathways. The compound is isolated from Paeoniae Alba and used for natural product chemistry research.
|
| ln Vivo |
In vivo studies on 2-Hydroxynaringenin are limited, and published in vivo data are not available. Based on studies with naringenin (the non-hydroxylated parent compound) and other hydroxylated flavonoids, 2-Hydroxynaringenin would be expected to exhibit in vivo anti-inflammatory effects in animal models such as carrageenan-induced paw edema, croton oil-induced ear edema, and acetic acid-induced writhing (pain model). Naringenin shows anti-inflammatory effects when administered orally or topically. The compound may also exhibit antinociceptive (pain-relieving) and cardioprotective properties.
|
| Enzyme Assay |
Cell-free antioxidant assay protocol (DPPH radical scavenging): Varying concentrations of 2-Hydroxynaringenin (e.g., 1-200 microM) are mixed with DPPH (2,2-diphenyl-1-picrylhydrazyl) radical solution in methanol or ethanol. The mixture is incubated at room temperature for 30 minutes in the dark. Absorbance is measured at 517 nm. The percentage of radical scavenging is calculated as [(Acontrol - Asample)/Acontrol] × 100%. IC50 values are determined from dose-response curves. Ascorbic acid or Trolox is used as a positive control. The ABTS radical cation decolorization assay and FRAP (ferric reducing antioxidant power) assay can also be used.
|
| Cell Assay |
Cell-based anti-inflammatory assay: Macrophages (e.g., RAW 264.7 cells) are seeded in 96-well plates and pre-incubated with 2-Hydroxynaringenin at various concentrations (e.g., 1-100 microM) for 1 hour, then stimulated with lipopolysaccharide (LPS, 0.1-1 microg/mL) for 18-24 hours. Nitric oxide (NO) production is measured by the Griess reagent. Pro-inflammatory cytokine levels (TNF-alpha, IL-1beta, IL-6) are measured by ELISA in culture supernatants. Cell viability is assessed by MTT assay to exclude cytotoxicity. The compound should suppress NO and cytokine production in a concentration-dependent manner.
|
| Animal Protocol |
In vivo anti-inflammatory protocol (based on naringenin studies): Swiss albino mice or Wistar rats are used. Edema is induced by sub-plantar injection of carrageenan (0.1 mL of 1% solution in saline) into the right hind paw. Test compound 2-Hydroxynaringenin (or naringenin as a reference) is administered orally (e.g., 10-50 mg/kg) or intraperitoneally 1 hour before carrageenan challenge. Paw volume is measured at 0, 1, 2, 3, 4, and 6 hours post-injection using a plethysmometer or calipers. The percentage inhibition of edema is calculated relative to vehicle-treated control group. Indomethacin (10 mg/kg) is often used as a positive control.
|
| ADME/Pharmacokinetics |
Pharmacokinetic data for 2-Hydroxynaringenin are not available. Based on data for naringenin (which has good oral absorption but extensive first-pass metabolism), this flavonoid is likely absorbed after oral administration, undergoes extensive conjugation (glucuronidation and sulfation) in the intestinal wall and liver, and circulates primarily as conjugated metabolites. The free aglycone form may have low systemic bioavailability due to rapid phase II metabolism. Peak plasma concentrations are typically reached within 1-3 hours of oral administration in animal models. The elimination half-life is likely 2-6 hours in rodents.
|
| Toxicity/Toxicokinetics |
Specific toxicity studies for 2-Hydroxynaringenin have not been published. However, flavonoids, including naringenin, are generally considered safe with low toxicity. Naringenin has an LD50 >2000 mg/kg in rodents and is well-tolerated in short-term animal studies. The additional hydroxyl group in 2-Hydroxynaringenin may increase its antioxidant activity but is not expected to significantly alter its safety profile. However, as with all research chemicals, appropriate safety precautions should be taken. The compound should be handled in a fume hood with gloves and protective eyewear.
|
| References | |
| Additional Infomation |
2,5,7-Trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one is a tetrahydroxyflavanone with hydroxyl groups located at positions 2, 4', 5, and 7. It is a plant metabolite. It is a tetrahydroxyflavanone and a member of the 2-hydroxyflavanone family.
2-Hydroxynaringenin is not a drug and has no clinical applications or regulatory approval. It is a naturally occurring flavonoid isolated from Paeoniae Alba (white peony root) and is used as a research tool in natural product chemistry, phytochemistry, and pharmacognosy studies. The compound is of interest for its potential antioxidant and anti-inflammatory properties, which may contribute to cardiovascular health and chronic disease prevention. It serves as an analytical standard for identifying hydroxylated flavonoids in plant extracts and for studying the structure-activity relationships of polyphenolic compounds. Not for human consumption. |
| Molecular Formula |
C15H12O6
|
|---|---|
| Molecular Weight |
288.25
|
| Exact Mass |
288.063
|
| CAS # |
58124-18-8
|
| PubChem CID |
21932272
|
| Appearance |
White to off-white solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
635.0±55.0 °C at 760 mmHg
|
| Flash Point |
245.7±25.0 °C
|
| Vapour Pressure |
0.0±2.0 mmHg at 25°C
|
| Index of Refraction |
1.736
|
| LogP |
2.25
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
21
|
| Complexity |
405
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
Oc1ccc(cc1)C3(O)CC(=O)c2c(cc(O)cc2O)O3
|
| InChi Key |
NFENYLPEYDNIMO-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C15H12O6/c16-9-3-1-8(2-4-9)15(20)7-12(19)14-11(18)5-10(17)6-13(14)21-15/h1-6,16-18,20H,7H2
|
| Chemical Name |
2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3H-chromen-4-one
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
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 Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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)] Oral Formulations
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 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4692 mL | 17.3461 mL | 34.6921 mL | |
| 5 mM | 0.6938 mL | 3.4692 mL | 6.9384 mL | |
| 10 mM | 0.3469 mL | 1.7346 mL | 3.4692 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
