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Homoeriodictyol

Alias: 5,7,4'-Trihydroxy-3'-methoxyflavanone; (-)-Homoeriodictyol; Homoeriodictyol; Eriodictyonone
Cat No.:V34577 Purity: ≥98%
Homoeriodictyol is the flavonoid metabolite of Eriocitrin.
Homoeriodictyol
Homoeriodictyol Chemical Structure CAS No.: 446-71-9
Product category: Natural Products
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Homoeriodictyol is the flavonoid metabolite of Eriocitrin. Eriocitrin is a potent antioxidant.
Homoeriodictyol is a methylated metabolite of eriodictyol, which is the aglycone of eriocitrin, a flavonoid glycoside present in lemon fruit. It is formed by O-methylation at the 3' position of the B ring of eriodictyol. In rats orally administered eriocitrin, Homoeriodictyol was detected in plasma and urine as both free and conjugated forms (glucuronide and/or sulfate conjugates). [1]
Biological Activity I Assay Protocols (From Reference)
ln Vivo
Following oral administration of eriocitrin (75 μmol/kg in distilled water) to male Sprague-Dawley rats, Homoeriodictyol was detected in the plasma at 4.0 h post-administration, but only after treatment with β-glucuronidase/sulfatase, indicating its presence as conjugated metabolites (glucuro and/or sulfo conjugates). Free (nonconjugate) Homoeriodictyol was not detected in plasma. In urine collected for 24 h after oral administration of eriocitrin (50 μmol/kg in distilled water), both nonconjugates and conjugates of Homoeriodictyol were detected. The plasma antioxidant activity (resistance to lipid peroxidation induced by AAPH) was significantly increased at 0.5, 1.0, 2.0, and 4.0 h post-administration of eriocitrin, and the presence of Homoeriodictyol (along with other metabolites) in plasma at 4.0 h may contribute to this antioxidative activity. [1]
Animal Protocol
Male Sprague-Dawley rats (5 weeks old, weighing 195-210 g) were fasted overnight, then administered eriocitrin (75 μmol/kg in distilled water) by gastric intubation. At different times (0.5, 1.0, 2.0, and 4.0 h) following administration, rats were anesthetized with ether, and blood was withdrawn from the abdominal aorta into heparinized tubes to obtain plasma.
For urine collection, rats were administered eriocitrin (50 μmol/kg in distilled water) by gastric intubation, and urine was collected for 24 h and 48 h. Plasma and urine samples were analyzed by HPLC and LC-MS for metabolites, including Homoeriodictyol. To detect conjugated forms, samples were treated with β-glucuronidase/sulfatase (5.4×10² units/mL of β-glucuronidase and 0.2×10² units/mL of sulfatase) for 20 min at 37°C before analysis. [1]
ADME/Pharmacokinetics
Homoeriodictyol is a metabolite of eriocitrin detected in rat plasma at 4.0 h after oral administration, existing exclusively in conjugated (glucuronide and/or sulfate) forms, as it was not detectable without β-glucuronidase/sulfatase treatment. [1]
In urine collected for 24 h following oral administration of eriocitrin, both nonconjugate (free) and conjugate forms of Homoeriodictyol were detected. [1]
Homoeriodictyol is formed by O-methylation at the 3' position of the B ring of eriodictyol, which is the aglycone of eriocitrin, and this methylation likely occurs in the liver. [1]
The total absorption ratio of eriocitrin (calculated from the sum of all detected metabolites, including Homoeriodictyol, in renal excreted urine) was 5.68% ± 0.32. [1]
References

[1]. Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats. J Agric Food Chem. 2000 Aug;48(8):3217-24.

Additional Infomation
High-sweet charantin is a trihydroxyflavanone composed of 3'-methoxyflavanones, with the three hydroxyl substituents located at positions 4', 5, and 7. It is a metabolite and flavoring agent. It is both a monomethoxyflavanone and a trihydroxyflavanone, belonging to the 3'-methoxyflavanone and 4'-hydroxyflavanone classes. Functionally, it is related to sweet charantin. High-sweet charantin has been reported to be found in Sichuan poplar, chili peppers, and other organisms with relevant data.
Homoeriodictyol is one of the main eriocitrin metabolites in vivo, together with eriodictyol and hesperetin. The o-dihydroxy structure at the 3' and 4' positions in the B ring of eriodictyol is considered important for antioxidative activity; O-methylation (forming Homoeriodictyol and hesperetin) seems to be responsible for the loss of antioxidant activity. [1]
The metabolic pathway of eriocitrin involves intestinal bacterial hydrolysis to eriodictyol, followed by absorption and subsequent methylation in the liver to produce Homoeriodictyol (3'-O-methyleriodictyol) and hesperetin (4'-O-methyleriodictyol). [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H14O6
Molecular Weight
302.27876
Exact Mass
302.079
Elemental Analysis
C, 63.58; H, 4.67; O, 31.76
CAS #
446-71-9
Related CAS #
690229-01-7 (sodium); 446-71-9 (free acid)
PubChem CID
73635
Appearance
White to off-white solid
Density
1.458g/cm3
Boiling Point
583.8ºC at 760mmHg
Melting Point
225-227ºC (dec.)
Flash Point
222.1ºC
Vapour Pressure
3.14E-14mmHg at 25°C
Index of Refraction
1.664
LogP
2.518
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
COC1=C(O)C=CC([C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)=C1
InChi Key
FTODBIPDTXRIGS-ZDUSSCGKSA-N
InChi Code
InChI=1S/C16H14O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-6,13,17-19H,7H2,1H3/t13-/m0/s1
Chemical Name
(2S)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms
5,7,4'-Trihydroxy-3'-methoxyflavanone; (-)-Homoeriodictyol; Homoeriodictyol; Eriodictyonone
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.

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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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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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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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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