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(Rac)-Hydnocarpin (Hydnocarpin racemate)

Alias: (Rac)-Hydnocarpin
Cat No.:V62055 Purity: ≥98%
(Rac)-Hydnocarpin is a natural flavonoid extracted from the Rhizoctonia spp.
(Rac)-Hydnocarpin (Hydnocarpin racemate)
(Rac)-Hydnocarpin (Hydnocarpin racemate) Chemical Structure CAS No.: 51419-48-8
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
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Product Description
(Rac)-Hydnocarpin is a flavonoid isolated from the Rhizoctonia spp. species and has moderate cytotoxicity against cancer cells.
(Rac)-Hydnocarpin (Hydnocarpin racemate) (CAS 51419-48-8) is a flavonoid lignan isolated from various medicinal plants including Hydnocarpus anthelminthica, Pueraria lobata, and Rhizoctonia spp. It has the molecular formula C₂₅H₂₀O₉ and a molecular weight of 464.42 g/mol. The compound exhibits strong anti-inflammatory, antioxidant, anticancer, and antimicrobial effects. In ovarian cancer cell lines, it demonstrates significant cytotoxicity while showing lower toxicity to normal ovarian epithelial cells. (Rac)-Hydnocarpin is used as a research tool for studying cancer therapy, inflammation control, and natural product pharmacology. It is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
PI3K/Akt, NF-κB, and MAPK signaling pathways. (Rac)-Hydnocarpin modulates key cellular pathways including PI3K/Akt, NF-κB, and MAPK, contributing to apoptosis induction and suppression of tumor cell proliferation. The compound primarily activates caspase-9 and caspase-3, triggering mitochondria-mediated apoptosis, with caspase-8 playing a lesser role. Reactive oxygen species generation plays a major regulatory role in its apoptotic process. The compound also inhibits multidrug resistance transporters, enhancing the efficacy of certain chemotherapeutic agents.
ln Vitro
(Rac)-Hydnocarpin exhibits moderate cytotoxicity against cancer cells. In ovarian cancer cell lines, it shows significant cytotoxic activity while maintaining lower toxicity to normal ovarian epithelial cells. The compound induces apoptosis primarily through the mitochondrial pathway, activating caspase-9 and caspase-3. It exhibits strong anti-inflammatory activity by modulating NF-κB signaling, antioxidant effects through free radical scavenging, and antimicrobial activity against various pathogens. The compound's antiproliferative effects are mediated through PI3K/Akt and MAPK pathway modulation.
ln Vivo
In vivo studies of (Rac)-Hydnocarpin are limited. As a flavonoid lignan with anticancer and anti-inflammatory activities, the compound has potential for evaluation in animal models of cancer and inflammation. Its ability to inhibit multidrug resistance transporters suggests potential for combination therapy approaches. The compound enhances the efficacy of certain chemotherapeutic agents by inhibiting multidrug resistance transporters. Further in vivo studies are needed to fully characterize its pharmacokinetic and pharmacodynamic properties, as well as its efficacy and safety profile.
Enzyme Assay
Non-cell-based assays for (Rac)-Hydnocarpin include enzyme inhibition studies to assess its effects on PI3K/Akt, NF-κB, and MAPK signaling components. Kinase activity assays using purified enzymes or cell lysates can measure the compound's inhibitory effects. Antioxidant activity is assessed using DPPH radical scavenging, ABTS, and FRAP assays. Antimicrobial activity is evaluated by broth microdilution for MIC determination against bacterial and fungal strains. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization and purity assessment.
Cell Assay
Cell-based assays for (Rac)-Hydnocarpin use various cancer cell lines, particularly ovarian cancer cell lines, to assess its cytotoxic and antiproliferative activity. Cells are cultured in appropriate medium and treated with the compound at various concentrations. Cell viability is measured using MTT, CCK-8, or SRB assays. Apoptosis is evaluated by flow cytometry using Annexin V/PI staining, caspase activity assays (caspase-3, caspase-9), and detection of apoptotic markers by Western blot. ROS generation is measured using fluorescent probes such as DCFH-DA. NF-κB, PI3K/Akt, and MAPK pathway activation are assessed by Western blot.
Animal Protocol
In vivo studies of (Rac)-Hydnocarpin are limited. Based on its biological activities, potential animal models include: tumor xenograft models for anticancer evaluation; carrageenan-induced paw edema models for anti-inflammatory assessment; and infection models for antimicrobial evaluation. Standard protocols for these models involve administration of the compound (oral, intraperitoneal, or intravenous) followed by measurement of relevant endpoints including tumor volume, inflammatory markers, and histopathological analysis. The compound's ability to inhibit multidrug resistance transporters suggests potential for combination therapy studies.
ADME/Pharmacokinetics
(Rac)-Hydnocarpin has a molecular formula of C₂₅H₂₀O₉ and a molecular weight of 464.42 g/mol. The IUPAC name is 5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one. Purity is ≥95%. The compound should be stored as a powder at -20°C for up to 3 years or in solvent at -80°C for up to 2 years. It is soluble in DMSO and other organic solvents. It is intended for research use only.
Toxicity/Toxicokinetics
Specific toxicity data for (Rac)-Hydnocarpin are limited. The compound exhibits moderate cytotoxicity against cancer cells while showing lower toxicity to normal ovarian epithelial cells, suggesting some selectivity for cancer cells. As a natural flavonoid lignan, it is generally considered to have low to moderate toxicity. However, comprehensive toxicological studies have not been reported. Standard laboratory safety practices should be followed when handling this compound, including the use of personal protective equipment. It is intended for research use only.
References

[1]. Exploring Mitochondria-Mediated Intrinsic Apoptosis by New Phytochemical Entities: An Explicit Observation of Cytochrome c Dynamics on Lung and Melanoma Cancer Cells. J Med Chem. 2019 Sep 12;62(17):8311-8329.

Additional Infomation
Reports indicate that honeysuckle and mullein contain hydnocarpin, and relevant data is available for reference.
(Rac)-Hydnocarpin (Hydnocarpin racemate) is a flavonoid lignan isolated from various medicinal plants including Hydnocarpus anthelminthica, Pueraria lobata, and Rhizoctonia spp. It exhibits strong anti-inflammatory, antioxidant, anticancer, and antimicrobial effects. Mechanistically, the compound modulates PI3K/Akt, NF-κB, and MAPK signaling pathways, contributing to apoptosis induction and suppression of tumor cell proliferation. It primarily activates the mitochondrial apoptosis pathway through caspase-9 and caspase-3. The compound also enhances the efficacy of certain chemotherapeutic agents by inhibiting multidrug resistance transporters. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C25H20O9
Molecular Weight
464.42
Exact Mass
464.11
CAS #
51419-48-8
PubChem CID
5489114
Appearance
Off-white to yellow solid
Density
1.5±0.1 g/cm3
Boiling Point
740.9±60.0 °C at 760 mmHg
Flash Point
257.8±26.4 °C
Vapour Pressure
0.0±2.6 mmHg at 25°C
Index of Refraction
1.685
LogP
2.66
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
4
Heavy Atom Count
34
Complexity
772
Defined Atom Stereocenter Count
0
SMILES
COc1cc(ccc1O)C2C(Oc3cc(ccc3O2)c4cc(=O)c5c(cc(cc5o4)O)O)CO
InChi Key
NMICSFNNFDNGEL-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H20O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-10,23,25-29H,11H2,1H3
Chemical Name
5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
Synonyms
(Rac)-Hydnocarpin
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 33.33 mg/mL (71.77 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.38 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.38 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.38 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1532 mL 10.7661 mL 21.5322 mL
5 mM 0.4306 mL 2.1532 mL 4.3064 mL
10 mM 0.2153 mL 1.0766 mL 2.1532 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.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

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