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Sternbin (Eriodictyol 7-methyl ether; 7-O-Methyleriodictyol)

Alias: Eriodictyol 7-methyl ether; 7-O-Methyleriodictyol; Sternbin
Cat No.:V61891 Purity: ≥98%
Sternbin is the detoxification metabolite of the rice flavanone phytoalexin Sakuranetin in Pyricularia oryzae.
Sternbin (Eriodictyol 7-methyl ether; 7-O-Methyleriodictyol)
Sternbin (Eriodictyol 7-methyl ether; 7-O-Methyleriodictyol) Chemical Structure CAS No.: 51857-11-5
Product category: Flavonoids
This product is for research use only, not for human use. We do not sell to patients.
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1mg
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Product Description
Sternbin is the detoxification metabolite of the rice flavanone phytoalexin Sakuranetin in Pyricularia oryzae. Sakuranetin is a flavanone phytoalexin linked to rice disease resistance.
Sternbin (Eriodictyol 7-methyl ether; 7-O-Methyleriodictyol) (CAS 51857-11-5) is a flavanone compound with the molecular formula C₁₆H₁₄O₆ and a molecular weight of 302.28 g/mol. It is the detoxification metabolite of the rice flavanone phytoalexin sakuranetin in Pyricularia oryzae. Sternbin can be isolated from Heliotropium sinuatum and other plant sources. It exhibits antibacterial activity against a wide range of bacteria and antiviral activity against infectious salmon anemia virus (ISAV). It also inhibits the contraction of isolated rat smooth muscle.
Biological Activity I Assay Protocols (From Reference)
Targets
Bacterial targets; viral targets; smooth muscle contractile machinery. Sternbin is a flavanone with antibacterial activity against a wide range of bacteria. It also shows antiviral activity against infectious salmon anemia virus (ISAV). Additionally, it inhibits the contraction of isolated rat smooth muscle, suggesting interaction with smooth muscle contractile pathways or calcium signaling.
ln Vitro
Sternbin (Eriodictyol 7-methyl ether) is a flavanone and antibacterial agent. It has antibacterial activity against a wide range of bacteria. Sternbin has antiviral activity against infectious salmon anemia virus (ISAV). It inhibits the contraction of isolated rat smooth muscle. As a flavanone, it may also exhibit antioxidant and anti-inflammatory properties common to this class of compounds.
ln Vivo
In vivo studies of Sternbin are limited. It is a detoxification metabolite of the rice flavanone phytoalexin sakuranetin in Pyricularia oryzae. Sakuranetin is a flavanone phytoalexin linked to rice disease resistance. Sternbin represents a detoxified form of this phytoalexin, suggesting its role in plant-pathogen interactions. Its antibacterial and antiviral activities suggest potential for further in vivo evaluation in infection models.
Enzyme Assay
Non-cell-based assays for Sternbin include antibacterial susceptibility testing using broth microdilution or agar diffusion methods to determine minimum inhibitory concentrations (MICs) against bacterial strains. Antiviral activity can be assessed using plaque reduction assays against infectious salmon anemia virus (ISAV). Smooth muscle contraction assays use isolated rat smooth muscle preparations in organ baths to measure inhibition of contractile responses. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization.
Cell Assay
Cell-based assays for Sternbin use various bacterial and viral culture models to assess antibacterial and antiviral activities. For antibacterial studies, bacterial cultures are treated with the compound at various concentrations, and growth inhibition is measured by optical density or colony counting. For antiviral studies, virus-infected cells are treated with the compound, and viral replication is assessed by plaque reduction or cytopathic effect inhibition assays. Cytotoxicity is assessed using standard cell viability assays.
Animal Protocol
In vivo studies of Sternbin are limited. Based on its antibacterial and antiviral activities, potential animal models include bacterial or viral infection models. As a plant metabolite, it may be studied in plant-pathogen interaction models. Standard protocols for infection models involve administration of the compound followed by measurement of relevant endpoints such as pathogen load, survival, and tissue pathology. Further studies are needed to characterize its in vivo efficacy and safety.
ADME/Pharmacokinetics
Sternbin has a molecular formula of C₁₆H₁₄O₆ and a molecular weight of 302.28 g/mol. The IUPAC name is (S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychroman-4-one. It is also known as eriodictyol 7-methyl ether and 7-O-methyleriodictyol. It is a detoxification metabolite of the rice flavanone phytoalexin sakuranetin. It should be stored under recommended conditions and is intended for research use only.
Toxicity/Toxicokinetics
Specific toxicity data for Sternbin are limited. As a natural flavanone, it is generally considered to have low toxicity. It exhibits antibacterial and antiviral activities, indicating biological activity at certain concentrations. Standard laboratory safety practices should be followed when handling this compound. It is intended for research use only.
References

[1]. Identification of Sternbin and Naringenin as Detoxified Metabolites from the Rice Flavanone Phytoalexin Sakuranetin by Pyricularia oryzae. Chem Biodivers. 2017 Feb;14(2).

Additional Infomation
7-O-methylsuccinol has been reported to be found in Artemisia, Brumemeria, and other organisms with available data.
Sternbin (Eriodictyol 7-methyl ether) is a flavanone and antibacterial agent isolated from Heliotropium sinuatum. It is the detoxification metabolite of the rice flavanone phytoalexin sakuranetin in Pyricularia oryzae. Sakuranetin is a flavanone phytoalexin linked to rice disease resistance. Sternbin has antibacterial activity against a wide range of bacteria and antiviral activity against infectious salmon anemia virus (ISAV). It also inhibits the contraction of isolated rat smooth muscle. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H14O6
Molecular Weight
302.28
Exact Mass
302.079
CAS #
51857-11-5
PubChem CID
1268276
Appearance
White to off-white solid
Density
1.5±0.1 g/cm3
Boiling Point
607.2±55.0 °C at 760 mmHg
Flash Point
231.3±25.0 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.665
LogP
2.77
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
2
Heavy Atom Count
22
Complexity
413
Defined Atom Stereocenter Count
1
SMILES
O1C2=C([H])C(=C([H])C(=C2C(C([H])([H])[C@@]1([H])C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])=O)O[H])OC([H])([H])[H]
InChi Key
DSAJORLEPQBKDA-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
Chemical Name
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one
Synonyms
Eriodictyol 7-methyl ether; 7-O-Methyleriodictyol; Sternbin
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)
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
(e.g. IP/IV/IM/SC)
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 : PEG300Tween 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 : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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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


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.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3082 mL 16.5410 mL 33.0819 mL
5 mM 0.6616 mL 3.3082 mL 6.6164 mL
10 mM 0.3308 mL 1.6541 mL 3.3082 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.

Calculator

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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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