A natural antioxidant
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Keracyanin (chloride)

Item No. 15778

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyrylium, monochloride
CAS Number
18719-76-1
Synonyms
  • Cyanidin 3-rutinoside
  • Meralop
  • Sambucin
Molecular Formula
C27H31O15 • Cl
Formula Weight
631.0
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
283, 539 nm
SMILES
OC(C(O)=C1)=CC=C1C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]5[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O5)O4.[Cl-]
InChi Code
InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+
InChi Key
ADZHXBNWNZIHIX-XYGAWYNKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

    $190

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    Cayman Chemical
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    Product Description

    Keracyanin (chloride) is a polyphenolic anthocyanin found naturally in many plants.1 It has high antioxidant activity, protecting erythrocytes from apoptosis.1,2 However, keracyanin (chloride) impairs growth and induces apoptosis in the highly tumorigenic RE-149 DHD cell line.3 It inhibits a range of mammalian and bacterial proteases, including neutrophil elastase, matrix metalloproteinase-1 (MMP-1), and MMP-9 at concentrations of 6.25-50 µg/ml.4 When added to food, keracyanin (chloride) significantly reduces body weight gain, resistance to insulin, and lipid accumulation in mice fed a high-fat diet.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tyl, C.E., and Bunzel, M. Antioxidant activity-guided fractionation of blue wheat (UC66049 Triticum aestivum L.). J. Agric. Food Chem. 60(3), 731-739 (2012).

    2. Zhang, J., Hou, X., Ahmad, H., et al. Assessment of free radicals scavenging activity of seven natural pigments and protective effects in AAPH-challenged chicken erythrocytes. Food Chem. 145, 57-65 (2014).

    3. Zikri, N.N., Riedl, K.M., Wang, L.S., et al. Black raspberry components inhibit proliferation, induce apoptosis, and modulate gene expression in rat esophageal epithelial cells. Nutr. Cancer 61(6), 816-826 (2009).

    4. Santos, J., La, V.D., Bergeron, C., et al. Inhibition of host- and bacteria-derived proteinases by natural anthocyanins. J. Periodontal. Res. 46(5), 550-557 (2011).

    5. Wu, T., Qi, X., Liu, Y., et al. Dietary supplementation with purified mulberry (Morus australis Poir) anthocyanins suppresses body weight gain in high-fat diet fed C57BL/6 mice. Food Chem. 141(1), 482-487 (2013).