A flavanol dimer with diverse biological properties
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Isomer(s)
38893Procyanidin A1
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Procyanidin A2

Item No. 25200

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3R,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol
CAS Number
41743-41-3
Synonyms
  • (+)-Epicatechin-(4β-8,2β-O-7)-epicatechin
  • Proanthocyanidin A2
  • Procyanidin dimer A2
  • Procyanidol A2
Molecular Formula
C30H24O12
Formula Weight
576.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
λmax
282 nm
SMILES
OC1=C(C[C@@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)C3=C([C@@]([C@@]4([H])O)([H])C(C(O)=CC(O)=C5)=C5O[C@@]4(C6=CC(O)=C(O)C=C6)O7)C7=C1
InChi Code
InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1
InChi Key
NSEWTSAADLNHNH-LSBOWGMISA-N
Origin
Plant/Grape seeds
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Procyanidin A2 is a natural flavanol dimer of (–)–epicatechin (Item No. 11807) that is found in the horse chestnut (A. hippocastanum), mountain cranberry (V. vitis-idaea), and other fruits with antioxidant, anti-inflammatory, antibacterial, antiproliferative, and antidiabetic properties.1,2,3,4,5 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals (IC50 = 5.08 μM) and inhibits STAT3 activation induced by platelet derived growth factor (PDGF) in primary rat vascular smooth muscle cells (VSMCs) when used at a concentration of 30 μg/ml.3,4 Procyanidin A2 inhibits growth of S. aureus and E. coli (MICs = 62.5 and 62.5 μg/ml, respectively) and proliferation of human HepG2 liver hepatocellular carcinoma and HeLa cervical cancer cells (EC50s = 62.19 and 66.07 μg/ml, respectively).3 It also increases insulin secretion from primary mouse pancreatic islets when used at a concentration of 10 μM in vitro and inhibits bisphenol A-induced glucose increases in fasted mice when administered at a dose of 10 μmol/kg per day.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jacques, D., Haslam, E., Bedford, G.R., et al. Structure of the dimeric proanthocyanidin-A2 and its derivatives. J.C.S. Chem. Comm. 15, 518-520 (1973).

    2. Ibrahim, S.R., and Mohamed, G.A. Litchi chinensis: Medicinal uses, phytochemistry, and pharmacology. J. Ethnopharmacol. 174, 492-513 (2015).

    3. Wen, L., Wu, D., Jiang, Y., et al. Identification of flavonoids in litchi (Litchi chinensis Sonn.) leaf and evaluation of anticancer activities. J. Funct. Foods 6, 555-563 (2014).

    4. Zhang, L., Shao, J., Zhou, Y., et al. Inhibition of PDGF-BB-induced proliferation and migration in VSMCs by proanthocyanidin A2: Involvement of KDR and Jak-2/STAT-3/cPLA2 signaling pathways. Biomed. Pharmacother. 98, 847-855 (2018).

    5. Ahangarpour, A., Afshari, G., Mard, S.A., et al. Preventive effects of procyanidin A2 on glucose homeostasis, pancreatic and duodenal homebox 1, and glucose transporter 2 gene expression disturbance induced by bisphenol A in male mice. J. Physiol. Pharmacol. 67(2), 243-252 (2016).