A flavonoid glycoside with diverse biological activities
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Isorhoifolin

Item No. 34036

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
552-57-8
Synonyms
  • Apigenin-7-O-rutinoside
Molecular Formula
C27H30O14
Formula Weight
578.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O=C1C2=C(O)C=C(O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)C=C2OC(C5=CC=C(C=C5)O)=C1
InChi Code
InChI=1S/C27H30O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-8,10,18,20-29,31-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
InChi Key
FKIYLTVJPDLUDL-SLNHTJRHSA-N
Origin
Fruit/Citrus peel
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Isorhoifolin is a flavonoid glycoside and an aglycone form of apigenin (Item No. 10010275) that has been found in M. longifolia and has diverse biological activities.1,2,3 It inhibits matrix metalloproteinase-1 (MMP-1), MMP-3, and MMP-13 (IC50s = 0.33, 2.45, and 0.22 µM, respectively).1 Isorhoifolin has antimutagenic properties in the E. coli WP2 tryptophan reverse mutation assay when used at a concentration of 2 µM.2 It is active against S. aureus and P. aeruginosa, but not E. coli or C. albicans, in agar diffusion assays when used at a concentration of 140 µg/ml.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Crasci, L., Basile, L., Panico, A., et al. Correlating in vitro target-oriented screening and docking: Inhibition of matrix metalloproteinases activities by flavonoids. Planta Med. 83(11), 901-911 (2017).

    2. Baris, O., Karadayi, M., Yanmis, D., et al. Isolation of 3 flavonoids from Mentha longifolia (L.) Hudson subsp. longifolia and determination of their genotoxic potentials by using the E. coli WP2 test system. J. Food. Sci. 76(9), T212-T217 (2011).

    3. Abu-Gharbieh, E., and Shehab, N.G. Therapeutic potentials of Crataegus azarolus var. eu- azarolus Maire leaves and its isolated compounds. BMC Complement. Altern. Med. 17(1), 218 (2017).