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Dihydrobaicalin

Alias: Dihydrobaicalin; 56226-98-3; CHEMBL467197; (2S,3S,4S,5R,6S)-6-[[(2S)-5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; (2S,3S,4S,5R,6S)-6-(((2S)-5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-7-yl)oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid; BDBM50250625;
Cat No.:V60990 Purity: ≥98%
Dihydrobaicalin is a flavonoid glycoside extracted from Scutellaria lateriflora L.
Dihydrobaicalin
Dihydrobaicalin Chemical Structure CAS No.: 56226-98-3
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
5mg
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Product Description
Dihydrobaicalin is a flavonoid glycoside extracted from Scutellaria lateriflora L.
Biological Activity I Assay Protocols (From Reference)
Targets
Natural flavonoid glycoside from American skullcap (Scutellaria lateriflora L.)
ln Vitro
The aqueous extract of American skullcap (Scutellaria lateriflora L. (S. lateriflora), Lamiaceae) has been traditionally used by North American Indians as a nerve tonic and for its sedative and diuretic properties. Recent reports stated that flavonoids and possibly amino acids are responsible for the anxiolytic activity. As a part of our search for environmentally friendly solvents to extract the active components from medicinal plants, we used S. lateriflora in a comparison of accelerated solvent extraction (ASE) using water, and supercritical fluid extraction (SFE) using CO2 and 10% EtOH as modifier, at different temperatures. Flavonoids and amino acids were quantified by HPLC−UV and HPLC−MS, respectively. The flavonoid content was compared with conventional extraction methods (hot water extraction and 70% ethanol). The use of ASE at 85 °C with water as solvent gave the best results for flavonoid glycosides and amino acids, whereas SFE gave higher yields of flavonoid aglycones. However, the results obtained for total flavonoids were not significatively superior to hot water extraction or 70% aqueous EtOH extract [1].
References

[1]. Comparison of the chemical composition of extracts from Scutellaria lateriflora using accelerated solvent extraction and supercritical fluid extraction versus standard hot water or 70% ethanol extraction. Journal of agricultural and food chemistry, 2005, 53(8): 3076-3080.

Additional Infomation
Dihydrobaicalin has been reported in Scutellaria scandens, Scutellaria amoena, and other organisms with data available.
ASE at lower temperature was the best technique to extract glutamine. There was no significant difference in the recovery when using ASE extraction temperatures between 85 and 100 °C. For GABA, the ethanolic extract (70%) allowed the highest recovery. A hot water extraction extract and the ASE 85 and 100 °C showed the second best recovery yields. As glutamine passes the blood−brain barrier and not GABA, the results obtained for glutamine are more important from an activity point of view. Among the conditions tested in this work, the use of the ASE at temperatures between 85 and 100 °C shows the most promise for glutamine. For tryptophan, phenylalanine, proline, glutamic acid, asparagine, tyrosine, isoleucine, leucine, and valine, an increase in the temperature in the ASE resulted in a decrease in the amino acid content. Only tryptophan was extracted with the SFE technique using ethanol as modifier. The use of the ASE, using water at 85 °C as solvent is a suitable technique for the extraction of polyphenolics from S. lateriflora, giving yields of total flavonoids similar to the conventional extraction techniques, but with a higher concentration of glutamine and a lower amount of GABA. Comparison of the hot water extraction, the ethanolic extract, and the ASE shows that there is no advantage to use of ASE with water for the extraction of the flavonoid glycosides. However, extraction with SFE-CO2 resulted in higher aglycone yields. In further experiments, an improvement of the experimental conditions of ASE and SFE-CO2 such as the use of lower temperatures or higher temperatures with lower pressure could be explored. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H20O11
Exact Mass
448.1
CAS #
56226-98-3
PubChem CID
14135325
Appearance
Typically exists as solid at room temperature
LogP
0.8
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
4
Heavy Atom Count
32
Complexity
695
Defined Atom Stereocenter Count
6
SMILES
C1[C@H](OC2=CC(=C(C(=C2C1=O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)C4=CC=CC=C4
InChi Key
UVNUGBQJLDGZKE-XDZPIWCFSA-N
InChi Code
InChI=1S/C21H20O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-5,7,10,16-19,21,23-27H,6H2,(H,28,29)/t10-,16-,17-,18+,19-,21+/m0/s1
Chemical Name
(2S,3S,4S,5R,6S)-6-[[(2S)-5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms
Dihydrobaicalin; 56226-98-3; CHEMBL467197; (2S,3S,4S,5R,6S)-6-[[(2S)-5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; (2S,3S,4S,5R,6S)-6-(((2S)-5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-7-yl)oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid; BDBM50250625;
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 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.)
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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)
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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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