A flavanone rutinoside with diverse biological activities
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Hesperidin

Item No. 18646

Technical Information
Formal Name
7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-(2S)-4-H-1-benzopyran-4-one
CAS Number
520-26-3
Synonyms
  • Cirantin
  • Hesperetin-7-β-rutinoside
  • Hesperidoside
  • NSC 44184
Molecular Formula
C28H34O15
Formula Weight
Purity
≥90%
A crystalline solid
DMF: 3 mg/mlDMSO: 5 mg/mlDMSO:PBS (pH 7.2)(1:5): 0.5 mg/ml
λmax
283 nm
SMILES
O=C1C2=C(O)C=C(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)O3)C=C2O[C@H](C5=CC=C(OC)C(O)=C5)C1
InChi Code
InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
InChi Key
QUQPHWDTPGMPEX-QJBIFVCTSA-N
Origin
Plant/Citrus aurantium L.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Hesperidin is a flavanone rutinoside that has been found in C. aurantium and has diverse biological activities.1,2,3,4,5,6 It reduces the formation of advanced glycation end products (AGEs) in a cell-free assay when used at a concentration of 1 mM.2 Hesperidin (10 nM) reduces NETosis induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in DMSO-differentiated HL-60 neutrophil-like cells.3 It decreases LPS-induced production of prostaglandin E2 (PGE2; Item No. 14010) and nitric oxide (NO) in RAW 264.7 cells when used at a concentration of 30 µM.4 Dietary administration of hesperidin (0.5 g/kg) prevents the formation of tongue neoplasms induced by 4-nitroquinoline 1-oxide (4-NDQ; Item No. 42994) in rats.5 It increases femoral bone mineral density in ovariectomized rats.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mizelle, J.W., Dunlap, W.J., Hagen, R.E., et alIsolation and identification of some flavanone rutinosides of the grapefruit. Anal. Biochem. 12(2), 316-324 (1965).

    2. Li, D., Mitsuhashi, S., and Ubukata, M. Protective effects of hesperidin derivatives and their stereoisomers against advanced glycation end-products formation. Pharm. Biol. 50(12), 1531-1535 (2012).

    3. Juanlu, C., Chen, L., Sung, C.-J., et alPhytochemicals as potential inhibitors of NETosis: Implications for immunothrombosis and chronic disease management. BMC Complement Med. Ther. (2026).

    4. Sakata, K., Hirose, Y., Qiao, Z., et alInhibition of inducible isoforms of cyclooxygenase and nitric oxide synthase by flavonoid hesperidin in mouse macrophage cell line. Cancer Lett. 199, 139-145 (2003).

    5. Tanaka, T., Makita, H., Ohnishi, M., et alChemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis by dietary curcumin and hesperidin: Comparison with the protective effect of β-carotene. Cancer Res. 54, 4653-4659 (1994).

    6. Habauzit, V., Nielsen, I.-L., Gil-Izquierdo, A., et alIncreased bioavailability of hesperetin-7-glucoside compared with hesperidin results in more efficient prevention of bone loss in adult ovariectomised rats. Br. J. Nutr. 102(7), 976-984 (2009).