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Delphinidin-3-O-arabinoside chloride

Alias: Delphinidin-3-O-arabinoside chloride
Cat No.:V62119 Purity: ≥98%
Delphinidin-3-O-arabinoside chloride is an anthocyanin compound.
Delphinidin-3-O-arabinoside chloride
Delphinidin-3-O-arabinoside chloride Chemical Structure CAS No.: 171370-55-1
Product category: Flavonoids
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Delphinidin-3-O-arabinoside chloride is an anthocyanin compound. Delphinidin-3-O-arabinoside chloride is a combination of a 3-O-arabinoside group and delphinidin, a naturally occurring purple anthocyanin. Rhododendron flowers can be used to isolate delphinidin-3-O-arabinoside in its furanose form.
Delphinidin-3-O-arabinoside chloride (CAS 171370-55-1) is a naturally occurring anthocyanin, a type of flavonoid pigment found in various fruits and vegetables. It consists of a delphinidin molecule linked to an arabinose sugar at the 3-position, along with a chloride ion. It has the molecular formula C₂₀H₁₉ClO₁₁ and a molecular weight of 470.81 g/mol. Delphinidin-3-O-arabinoside chloride is a dietary antioxidant. The compound exhibits several biological activities, including antioxidant, anti-inflammatory, hepatoprotective, antidiabetic, antimicrobial, neuroprotection, anti-adipogenesis, cardiovascular protection, and anticancer effects. It is found in pomace extracts of Saskatoon berries and other plant sources. The compound is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
Multiple targets including antioxidant enzymes, inflammatory mediators, and signaling pathways. Delphinidin-3-O-arabinoside chloride acts as a potent antioxidant by scavenging free radicals and reducing oxidative stress. The anthocyanin structure, particularly the presence of multiple hydroxyl groups on the B-ring, enables the compound to neutralize reactive oxygen species (ROS) and reactive nitrogen species (RNS). The compound also exhibits anti-inflammatory activity by modulating inflammatory signaling pathways, including the NF-κB pathway, and reducing the production of pro-inflammatory cytokines. Its cardioprotective effects are mediated through the inhibition of LDL oxidation and improvement of endothelial function. The compound's anticancer activity involves the induction of apoptosis and inhibition of cell proliferation.
ln Vitro
Delphinidin-3-O-arabinoside chloride exhibits significant antioxidant activity. It has been shown to scavenge free radicals and reduce oxidative stress in various in vitro systems. The compound demonstrates DPPH radical-scavenging capacity, ABTS radical scavenging capacity, reducing power, and oxygen radical absorbance capacity (ORAC). It has significantly higher antioxidant activity compared to Fe²⁺ controls. The compound also shows anti-inflammatory activity by reducing the production of inflammatory mediators. Its antimicrobial activity has been demonstrated against various bacterial and fungal strains. The compound's anticancer effects include inhibition of cancer cell proliferation and induction of apoptosis in various cancer cell lines.
ln Vivo
In vivo studies of delphinidin-3-O-arabinoside chloride are limited. As an anthocyanin, it is expected to be absorbed after oral administration and distributed to various tissues. Anthocyanins are known to undergo extensive metabolism, including deglycosylation, glucuronidation, and sulfation, and are eliminated primarily in urine and bile. The compound's antioxidant and anti-inflammatory activities suggest potential benefits in animal models of oxidative stress, inflammation, and metabolic disease. Further studies are needed to characterize its specific in vivo pharmacokinetic and pharmacodynamic properties.
Enzyme Assay
Non-cell-based assays for delphinidin-3-O-arabinoside chloride include standard antioxidant assays such as DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) radical scavenging, ferric reducing antioxidant power (FRAP), and oxygen radical absorbance capacity (ORAC) assays. These assays measure the compound's ability to scavenge free radicals or reduce oxidants in cell-free systems. For compound characterization, standard analytical methods including HPLC-UV, LC-MS/MS, and NMR are used to confirm identity and purity. The compound's stability under various conditions (pH, temperature, light) can be assessed using spectrophotometric methods.
Cell Assay
Cell-based assays for delphinidin-3-O-arabinoside chloride use various cell lines to assess its biological activities. For antioxidant studies, cells are exposed to oxidative stress inducers (e.g., H₂O₂) and treated with the compound, and intracellular ROS levels are measured using fluorescent probes such as DCFH-DA. For anti-inflammatory studies, macrophage cell lines (e.g., RAW 264.7) are stimulated with LPS and treated with the compound, and inflammatory mediators (NO, TNF-α, IL-6) in culture supernatant are measured. For anticancer studies, cancer cell lines are treated with the compound and cell viability (MTT), apoptosis (Annexin V/PI), and cell cycle progression are assessed.
Animal Protocol
In vivo studies of delphinidin-3-O-arabinoside chloride are limited. Based on its biological activities, potential animal models include: DSS-induced colitis models for anti-inflammatory evaluation; high-fat diet-induced obesity models for anti-adipogenesis and metabolic studies; and tumor xenograft models for anticancer evaluation. Standard protocols for these models involve administration of the compound (oral, intraperitoneal, or intravenous) followed by measurement of relevant endpoints including inflammatory markers, metabolic parameters, tumor volume, and histopathological analysis.
ADME/Pharmacokinetics
Delphinidin-3-O-arabinoside chloride has a molecular weight of 470.81 g/mol and a molecular formula of C₂₀H₁₉ClO₁₁. The SMILES notation is provided. The compound should be stored as a powder at -20°C for up to 3 years or in solvent at -80°C for 1 year. It can be shipped with blue ice or at ambient temperature. The compound is soluble in appropriate solvents for in vitro and in vivo studies. For in vivo formulation, standard protocols for anthocyanins can be used. The product can be stored for up to 24 months at 2-8°C if stored as stated on the product vial.
Toxicity/Toxicokinetics
Toxicological data for delphinidin-3-O-arabinoside chloride are limited. Anthocyanins are generally considered to have low toxicity and are widely consumed in the human diet as components of fruits and vegetables. No significant toxicity has been reported at dietary levels. High doses may cause gastrointestinal effects. The compound is intended for research use only. Standard laboratory safety practices should be followed when handling this compound, including the use of personal protective equipment.
References

[1]. Delphinidin 3-α-arabinopyranoside and other anthocyanins from flowers of Rhododendron cv. Lems Stormcloud[J]. Journal of Horticultural Science, 1995, 70(4): 637-642.

Additional Infomation
Delphinidin-3-O-arabinoside is a glycoside of flavonoids.
Delphinidin-3-O-arabinoside chloride is a naturally occurring anthocyanin found in various fruits and vegetables, including Saskatoon berries and other plant sources. Anthocyanins are water-soluble pigments responsible for the red, purple, and blue colors of many fruits and vegetables. They are known for their potent antioxidant and health-promoting properties. Delphinidin-3-O-arabinoside chloride is used as a reference standard for the identification and quantification of anthocyanins in plant extracts and food products. Its biological activities, including antioxidant, anti-inflammatory, and anticancer effects, make it a compound of interest for nutritional and pharmacological research. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H19CLO11
Molecular Weight
470.81
Exact Mass
470.061
CAS #
171370-55-1
PubChem CID
91810628
Appearance
Purple to purplish red solid
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
3
Heavy Atom Count
32
Complexity
596
Defined Atom Stereocenter Count
4
SMILES
[Cl-].O1C([H])([H])[C@]([H])([C@]([H])([C@@]([H])([C@@]1([H])OC1=C([H])C2=C(C([H])=C(C([H])=C2[O+]=C1C1C([H])=C(C(=C(C=1[H])O[H])O[H])O[H])O[H])O[H])O[H])O[H])O[H]
InChi Key
BQQCUFJAUJKCKH-GOWHUIJJSA-N
InChi Code
InChI=1S/C20H18O11.ClH/c21-8-3-10(22)9-5-15(31-20-18(28)17(27)13(25)6-29-20)19(30-14(9)4-8)7-1-11(23)16(26)12(24)2-7;/h1-5,13,17-18,20,25,27-28H,6H2,(H4-,21,22,23,24,26);1H/t13-,17-,18+,20-;/m0./s1
Chemical Name
(2S,3R,4S,5S)-2-[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxyoxane-3,4,5-triol;chloride
Synonyms
Delphinidin-3-O-arabinoside chloride
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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 2.1240 mL 10.6200 mL 21.2400 mL
5 mM 0.4248 mL 2.1240 mL 4.2480 mL
10 mM 0.2124 mL 1.0620 mL 2.1240 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?
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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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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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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