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Iriflophenone 3-C-glucoside

Alias: Iriflophenone 3Cglucoside; Iriflophenone 3 C glucoside
Cat No.:V40466 Purity: ≥98%
Iriflophenone 3-C-β-D-glucopyranoside, extracted from Cyclopia genistoides, has anti-oxidant effect.
Iriflophenone 3-C-glucoside
Iriflophenone 3-C-glucoside Chemical Structure CAS No.: 104669-02-5
Product category: New2
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
Iriflophenone 3-C-β-D-glucopyranoside, extracted from Cyclopia genistoides, has anti-oxidant effect.
Iriflophenone 3-C-glucoside (Iriflophenone 3-C-β-D-glucopyranoside) is a naturally occurring compound extracted from Cyclopia genistoides (honeybush). It has a molecular weight of 408.36 g/mol and molecular formula C19H20O10. The compound has antioxidant activity. It is used as a research tool for studying natural product chemistry and antioxidant mechanisms.
Biological Activity I Assay Protocols (From Reference)
Targets
Iriflophenone 3-C-glucoside targets oxidative stress pathways through its antioxidant activity. As a natural phenolic compound, it likely scavenges free radicals, chelates metal ions, and modulates cellular antioxidant defense systems. The C-glucosidic linkage at the 3-position may affect the compound's stability and bioavailability compared to O-glucosides. The compound's antioxidant activity makes it a potential candidate for studying oxidative stress-related diseases.
ln Vitro
In vitro studies have demonstrated that Iriflophenone 3-C-glucoside has antioxidant activity. It is extracted from Cyclopia genistoides (honeybush). The compound's antioxidant properties make it valuable for studying natural product chemistry and oxidative stress mechanisms. Further detailed in vitro characterization data, including IC50 values for various antioxidant assays, are available from the compound's isolation and characterization.
ln Vivo
In vivo studies of Iriflophenone 3-C-glucoside are limited. As a naturally occurring compound with antioxidant activity extracted from Cyclopia genistoides, it may have potential health benefits related to oxidative stress reduction. Honeybush tea, which contains this compound, has been consumed traditionally for its health benefits. However, specific in vivo pharmacokinetic and pharmacodynamic studies for the purified compound are limited.
Enzyme Assay
In vitro enzyme/receptor binding (non-cell) assays for Iriflophenone 3-C-glucoside typically involve antioxidant activity measurements. DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity is measured by incubating the compound with DPPH solution and measuring absorbance at 517 nm. ABTS radical scavenging, FRAP (ferric reducing ability), and ORAC (oxygen radical absorbance capacity) assays are also performed. Metal chelation activity can be assessed using ferrozine-based assays. IC50 values for radical scavenging are calculated from dose-response curves. The compound's antioxidant activity is compared to standard antioxidants such as Trolox or ascorbic acid.
Cell Assay
For in vitro cell-based assays, various cell lines (e.g., hepatocytes, neuronal cells, or endothelial cells) are cultured in appropriate media. Cells are treated with Iriflophenone 3-C-glucoside at concentrations ranging from 1-100 μM for 1-24 hours. Oxidative stress is induced by exposure to H₂O₂, or other oxidants. Cell viability is assessed by MTT or CCK-8 assays. Intracellular ROS levels are measured using DCFH-DA fluorescent probe. Antioxidant enzyme activities (SOD, catalase, GPx) are measured in cell lysates. Lipid peroxidation is assessed by measuring MDA levels. The compound's cytoprotective effects against oxidative stress are evaluated.
Animal Protocol
In vivo animal studies with Iriflophenone 3-C-glucoside are limited. The compound could be administered orally or intraperitoneally to rodents to study its antioxidant effects in vivo. Models of oxidative stress (e.g., CCl₄-induced hepatotoxicity, ischemia-reperfusion injury) could be used. Antioxidant enzyme activities and oxidative stress markers in tissues would be measured. However, specific published protocols are limited.
ADME/Pharmacokinetics
Iriflophenone 3-C-glucoside has a molecular weight of 408.36 g/mol and molecular formula C19H20O10. IUPAC name: (4-hydroxyphenyl)(2,4,6-trihydroxy-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanone. The compound is a C-glucoside. Storage recommendations: powder at -20°C for 3 years or 4°C for 2 years. Pharmacokinetic properties are characteristic of flavonoid glycosides, with limited oral bioavailability and metabolism by gut microbiota. The compound is intended for research purposes only.
Toxicity/Toxicokinetics
In preclinical studies, Iriflophenone 3-C-glucoside has shown a favorable safety profile as a naturally occurring compound. As a component of honeybush tea, it has a history of traditional use. The compound's antioxidant activity may provide protective effects against oxidative damage. Standard toxicology studies would be required for therapeutic development. The compound is intended for research purposes only and is not approved for human use.
References

[1]. Iriflophenone-3-C-glucoside from Cyclopia genistoides: isolation and quantitative comparison of antioxidant capacity with mangiferin and isomangiferin using on-line HPLC antioxidant assays. J Chromatogr B Analyt Technol Biomed Life Sci.

Additional Infomation
Reports indicate that agarwood contains irisone 3-C-glucoside, and relevant data is available for reference.
Iriflophenone 3-C-glucoside (Iriflophenone 3-C-β-D-glucopyranoside) is a naturally occurring compound extracted from Cyclopia genistoides (honeybush). It has a molecular weight of 408.36 g/mol and molecular formula C19H20O10. The compound has antioxidant activity. It is used as a research tool for studying natural product chemistry and antioxidant mechanisms. Iriflophenone 3-C-glucoside is not FDA-approved and is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₉H₂₀O₁₀
Molecular Weight
408.36
Exact Mass
408.105
CAS #
104669-02-5
PubChem CID
184358
Appearance
Off-white to light yellow solid powder
Density
1.7±0.1 g/cm3
Boiling Point
669.9±55.0 °C at 760 mmHg
Flash Point
239.9±25.0 °C
Vapour Pressure
0.0±2.2 mmHg at 25°C
Index of Refraction
1.734
LogP
2.35
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
4
Heavy Atom Count
29
Complexity
565
Defined Atom Stereocenter Count
5
SMILES
C1=CC(=CC=C1C(=O)C2=C(C=C(C(=C2O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
InChi Key
BZYKNVLTMWYEFA-ZJKJAXBQSA-N
InChi Code
InChI=1S/C19H20O10/c20-6-11-15(25)17(27)18(28)19(29-11)13-10(23)5-9(22)12(16(13)26)14(24)7-1-3-8(21)4-2-7/h1-5,11,15,17-23,25-28H,6H2/t11-,15-,17+,18-,19+/m1/s1
Chemical Name
(4-hydroxyphenyl)-[2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methanone
Synonyms
Iriflophenone 3Cglucoside; Iriflophenone 3 C glucoside
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 : ~100 mg/mL (~244.88 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.12 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 (6.12 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
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 (6.12 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 2.4488 mL 12.2441 mL 24.4882 mL
5 mM 0.4898 mL 2.4488 mL 4.8976 mL
10 mM 0.2449 mL 1.2244 mL 2.4488 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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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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