A flavanone
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Narirutin

Item No. 25124

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
14259-46-2
Synonyms
  • Naringenin-7-O-rutinoside
  • (2S)-Narirutin
Molecular Formula
C27H32O14
Formula Weight
580.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
212, 226, 284, 332 nm
SMILES
OC1=C(C(C[C@@H](C2=CC=C(O)C=C2)O3)=O)C3=CC(O[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)=C1
InChi Code
InChI=1S/C27H32O14/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/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
InChi Key
HXTFHSYLYXVTHC-AJHDJQPGSA-N
Origin
Plant/Aurantii fructus immaturus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    Narirutin is a flavanone originally isolated from C. paradisi that has anti-inflammatory and antidepressant-like activities.1 It reduces airway sensitivity, eosinophil counts and IL-4 levels in bronchoalveolar lavage fluid (BALF), and serum IgE levels in an ovalbumin mouse model of allergic eosinophilic airway inflammation when administered at a dose of 10 mg/kg.2 Narirutin decreases immobility in the forced swim test and latency to feeding in the novelty-suppressed feeding test, indicating antidepressant-like activity in a mouse model of chronic mild stress-induced depression.3

    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 al. Isolation and identification of some flavanone rutinosides of the grapefruit. Anal. Biochem. 12(2), 316-324 (1965).

    2. Funaguchi, N., Ohno, Y., La, B.L.B., et al. Narirutin inhibits airway inflammation in an allergic mouse model. Clin. Exp. Pharmacol. Physiol. 34(8), 766-770 (2007).

    3. Li, Y., Du, Y., Yang, J., et al. Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model. Neuroreport 29(15), 1264-1268 (2018).