A polyphenol flavonoid with HIV-related and antioxidant activities
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Procyanidin C1

Item No. 25201

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,2'R,2''R,3R,3'R,3''R,4R,4'S)-2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-[4,8':4',8''-ter-2H-1-benzopyran]-3,3',3'',5,5',5'',7,7',7''-nonol
CAS Number
37064-30-5
Synonyms
  • Proanthocyanidin C1
  • Procyanidol C1
Molecular Formula
C45H38O18
Formula Weight
866.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
282 nm
SMILES
OC1=CC=C([C@H]2OC(C([C@H]3C4=C(O)C=C(O)C=C4O[C@H](C5=CC(O)=C(O)C=C5)[C@@H]3O)=C(O)C=C6O)=C6[C@H](C7=C(O)C=C(O)C8=C7O[C@H](C9=CC=C(O)C(O)=C9)[C@H](O)C8)[C@H]2O)C=C1O
InChi Code
InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1
InChi Key
MOJZMWJRUKIQGL-XILRTYJMSA-N
Origin
Plant/Crataegi fructus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $118

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    5 mg

    $442

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    10 mg

    $736

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    Product Description

    Procyanidin C1 is a polyphenol flavonoid trimer of (–)-epicatechin (Item No. 11807) that has HIV-related and antioxidant activities.1,2 It activates latent HIV-1 provirus in JLR2 cells when used at concentrations ranging from 12.5 to 50 µM and increases NF-κB-dependent transcriptional activity in Jurkat T cells.1 Procyanidin C1 also scavenges 2,2’-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 3.2 µg/ml) and inhibits the activity of α-glucosidase (IC50 = 3.8 µg/ml) and 15-lipoxygenase (15-LO; IC50 = 57.6 µg/ml).2 Procyanidin C1 (10 µg/ml) prevents phosphorylation of ERK1/2 and the production of reactive oxygen species (ROS) in THP-1 cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hori, T., Barnor, J., Huu, T.N., et al. Procyanidin trimer C1 derived from Theobroma cacao reactivates latent human immunodeficiency virus type 1 provirus. Biochem. Biophys. Res. Commun. 459(2), 288-293 (2015).

    2. Bräunlich, M., Slimestad, R., Wangensteen, H., et al. Extracts, anthocyanins and procyanidins from Aronia melanocarpa as radical scavengers and enzyme inhibitors. Nutrients 5(3), 663-678 (2013).

    3. Terra, X., Palozza, P., Fernandez-Larrea, J., et al. Procyanidin dimer B1 and trimer C1 impair inflammatory response signalling in human monocytes. Free Radic. Res. 45(5), 611-619 (2011).

    Product Citations

    Racine, K.C., Iglesias-Carres, L., Herring, J.A., et al. Epicatechin and high-molecular weight fraction do not recapitulate the antiobesity and antidiabetes activities of whole cocoa extract. J. Agric. Food Chem. 74(26), 20500-20516 (2026).