Proanthocyanidin (Procyanidin) is a class of polyphenolic compounds widely distributed in higher plants, consisting of electrophilic flavanyl units. Proanthocyanidin works as an antioxidant and anticancer agent. Proanthocyanidin also displays anti-inflammatory, cardioprotective, antibacterial and antifungal properties and may be used to study chronic venous insufficiency, capillary fragility, sunburn and retinopathy.

Physicochemical Properties

Molecular Formula	C30H26O13
Molecular Weight	594.519649982452
Exact Mass	594.137
CAS #	20347-71-1
PubChem CID	107876
Appearance	Light brown to black solid powder
Density	1.9±0.1 g/cm3
Boiling Point	986.4±65.0 °C at 760 mmHg
Flash Point	550.3±34.3 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.876
LogP	1.46
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	4
Heavy Atom Count	43
Complexity	957
Defined Atom Stereocenter Count	0
InChi Key	HGVVOUNEGQIPMS-UHFFFAOYSA-N
InChi Code	InChI=1S/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2
Chemical Name	2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-3,4-dihydrochromene-3,4,5,7-tetrol
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)

Biological Activity

ln Vitro	Complex polymer combinations called proanthocyanidins are found in plants. Berries such as cranberries, apples, pears, and red wine, together with tea and chocolate, are the main sources of nutrition[1]. Because proanthocyanidin is found in cranberries (Vaccinium macrocarpon Ait.), it has the most intriguing antibacterial activity. The efficacy of cranberry consumption in avoiding urinary tract infections (UTIs) has been proven by several clinical trials. Escherichia coli is responsible for about 85% of UTIs, despite the fact that numerous other microbes can also cause them. As P-fimbriae are proteinaceous fibers on the bacterial cell wall, they are responsible for attachment to uroepithelial cells, which is why their presence on E. coli has been clearly identified as a virulence factor. According to recent research, cranberry proanthocyanidin may prevent P-fimbriated E. coli from sticking to uroepithelial cells. It seems that proanthocyanidin with at least one A-type linkage is associated with the antiadhesion activity of cranberry juice[1].
ln Vivo	Investigated are the effects of Proanthocyanidin from cacao liquor on 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine-induced mutagenesis and in vivo carcinogenesis in female Sprague-Dawley rats. When tested in the presence of the S-9 mixture, proanthocyanidin exhibits potent antimutagenic actions in the Ames test. They also considerably suppress breast carcinogenesis, but not rat pancreatic carcinogenesis in the start stage[1].
References	[1]. Proanthocyanidins, anthocyanins and cardiovascular diseases. Food research international 2014 v.59 pp. 41-52. [2]. Proanthocyanidins in health care: current and new trends. Curr Med Chem. 2004 May;11(10):1345-59.
Additional Infomation	Procyanidin is oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions. Procyanidin has been reported in Lathyrus laxiflorus, Vitis amurensis, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL H2O : 5 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (Infinity mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. 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 (Infinity 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	1.6820 mL	8.4101 mL	16.8203 mL
	5 mM	0.3364 mL	1.6820 mL	3.3641 mL
	10 mM	0.1682 mL	0.8410 mL	1.6820 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.