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Procyanidin B3

Alias: 2,3-trans-proanthocyanidin; Catechin(4a->8)catechin; Proanthocyanidin B3
Cat No.:V13155 Purity: ≥98%
Procyanidin B3 is a naturally occurring compound and a specific inhibitor of histone acetyltransferase (HAT).
Procyanidin B3
Procyanidin B3 Chemical Structure CAS No.: 23567-23-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
100mg
Other Sizes

Other Forms of Procyanidin B3:

  • Cyanidin Chloride
  • Procyanidin B1
  • Procyanidin B2
  • Procyanidin C1
  • Procyanidin A2
  • Procyanidin A1
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Top Publications Citing lnvivochem Products
Product Description
Procyanidin B3 is a naturally occurring compound and a specific inhibitor of histone acetyltransferase (HAT). It can bind to other sites of p300 instead of the active site, and selectively inhibits p300-mediated acetylation of androgen receptors. Procyanidin B3 has no effect on HDACs or histone methyltransferases (HMTs).
Procyanidin B3 (CAS#: 23567-23-9) is a B-type proanthocyanidin, a natural polyphenolic compound found in various plants, including cocoa, grapes, apples, and tea. It is a dimer of catechin and epicatechin linked through a 4→8 bond. Procyanidin B3 has been studied for its antioxidant, anti-inflammatory, and cardiovascular protective effects. The compound is a member of the flavan-3-ol family of polyphenols. Its molecular formula is C30H26O12 and molecular weight is 578.52 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Procyanidin B3 targets multiple pathways. It acts as a potent antioxidant by scavenging free radicals and chelating metal ions. It inhibits the activity of pro-inflammatory enzymes such as COX-2 and iNOS, reducing the production of inflammatory mediators. Procyanidin B3 also modulates the NF-κB signaling pathway, reducing the expression of pro-inflammatory cytokines. It has been shown to inhibit the activity of matrix metalloproteinases (MMPs), which are involved in tissue remodeling and cancer metastasis.
ln Vitro
In vitro, procyanidin B3 demonstrates potent antioxidant activity in various free radical scavenging assays, including DPPH and ABTS assays. It exhibits anti-inflammatory activity by reducing the production of pro-inflammatory cytokines (TNF-α, IL-6, IL-1β) in stimulated macrophages. The compound also shows inhibitory effects on cancer cell proliferation and induces apoptosis in various cancer cell lines. Specific IC50 values vary depending on the cell line and assay conditions.
ln Vivo
In vivo, procyanidin B3 has been studied for its cardiovascular protective effects, including reducing blood pressure, improving endothelial function, and reducing oxidative stress. It has also shown anti-inflammatory effects in animal models of inflammation. The compound's antioxidant properties contribute to its protective effects against oxidative stress-related diseases. Specific dosing regimens and efficacy outcomes are available in the scientific literature.
Enzyme Assay
The in vitro activity of procyanidin B3 is assessed using various biochemical and cell-based assays. For antioxidant activity, DPPH and ABTS radical scavenging assays are performed by incubating the compound with the radical solution and measuring the decrease in absorbance. For anti-inflammatory activity, macrophages are stimulated with LPS and treated with procyanidin B3, and cytokine production is measured by ELISA. The expression of COX-2, iNOS, and other inflammatory mediators is analyzed by Western blotting or qPCR.
Cell Assay
For cellular assays, macrophages (RAW 264.7), cancer cell lines, or endothelial cells are cultured in appropriate media and treated with various concentrations of procyanidin B3 (typically 1-100 μM) for 24-48 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. Cytokine production is measured by ELISA. ROS generation is measured using DCFH-DA fluorescence. The expression of target proteins is analyzed by Western blotting. Apoptosis is evaluated by flow cytometry using Annexin V/PI staining.
Animal Protocol
In vivo, procyanidin B3 is typically administered orally to animal models. In cardiovascular studies, animals are treated with procyanidin B3 at doses ranging from 10-100 mg/kg daily for several weeks, and blood pressure, endothelial function, and oxidative stress markers are assessed. In anti-inflammatory studies, animals are treated with procyanidin B3 before or after induction of inflammation, and inflammatory markers in serum and tissues are measured. Tissue samples are collected for histopathological and biochemical analysis.
ADME/Pharmacokinetics
Procyanidin B3 has a molecular weight of 578.52 g/mol and a molecular formula of C30H26O12. It is a polyphenolic compound with limited water solubility but good solubility in organic solvents such as DMSO and ethanol. The compound should be stored at -20°C under appropriate conditions to maintain stability. Pharmacokinetic parameters such as bioavailability and half-life vary depending on the route of administration and formulation.
Toxicity/Toxicokinetics
Specific toxicity data for procyanidin B3 is not detailed in the provided search results. As a natural polyphenol, it is generally considered to have low toxicity. In vitro studies at concentrations up to 100 μM did not show significant cytotoxicity in most cell lines. The compound is generally recognized as safe based on its presence in various foods. However, comprehensive toxicological studies are required to establish its full safety profile.
References

[1]. Procyanidin B3, an inhibitor of histone acetyltransferase, enhances the action of antagonist for prostate cancer cells via inhibition of p300-dependent acetylation of androgen receptor. Biochem J. 2011 Jan 1;433(1):235-44.

[2]. Procyanidin B3 prevents articular cartilage degeneration and heterotopic cartilage formation in a mouse surgical osteoarthritis model. PLoS One, 2012, 7(5): e37728.

Additional Infomation
Procyanidin B3 is a Procyanidin composed of two (+)-catechin molecules linked by a bond between the 4' and 8' positions of the α configuration. It is found in red wine, barley, beer, peaches, and the large-flowered jatropha (Jatropha macrantha, also known as Huanarpo Macho). It functions as a metabolite, antioxidant, anti-inflammatory agent, and EC 2.3.1.48 (histone acetyltransferase) inhibitor. It is a hydroxyflavanol, Procyanidin, biflavonoid, and polyphenol compound whose function is related to (+)-catechins. Procyanidin B3 has been reported to be found in tea (Camellia sinensis), peony (Paeonia obovata), and other organisms with relevant data.
Procyanidin B3 is a natural polyphenolic compound with potent antioxidant, anti-inflammatory, and cardiovascular protective effects. It is found in various foods, including cocoa, grapes, apples, and tea, and is part of the proanthocyanidin family of flavonoids. The compound has been extensively studied for its health benefits and potential therapeutic applications. Procyanidin B3 is not approved as a pharmaceutical drug but is available as a research compound and dietary supplement ingredient.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H26O12
Molecular Weight
578.53
Exact Mass
578.142
CAS #
23567-23-9
Related CAS #
Cyanidin Chloride;528-58-5;Procyanidin B1;20315-25-7;Procyanidin B2;29106-49-8;Procyanidin C1;37064-30-5;Procyanidin A2;41743-41-3;Procyanidin A1;103883-03-0
PubChem CID
146798
Appearance
White to light yellow solid powder
Density
1.7±0.1 g/cm3
Boiling Point
955.3±65.0 °C at 760 mmHg
Melting Point
218-219℃
Flash Point
531.6±34.3 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.803
LogP
0.3
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
3
Heavy Atom Count
42
Complexity
925
Defined Atom Stereocenter Count
5
SMILES
C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
InChi Key
XFZJEEAOWLFHDH-AVFWISQGSA-N
InChi Code
InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1
Chemical Name
(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms
2,3-trans-proanthocyanidin; Catechin(4a->8)catechin; Proanthocyanidin B3
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)
DMSO : ~50 mg/mL (~86.43 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.32 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 (4.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7285 mL 8.6426 mL 17.2852 mL
5 mM 0.3457 mL 1.7285 mL 3.4570 mL
10 mM 0.1729 mL 0.8643 mL 1.7285 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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g/mol

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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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