An iridoid glycoside with diverse biological activities
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Gentiopicrin

Item No. 25102

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,6S)-5-ethenyl-6-(β-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one
CAS Number
20831-76-9
Synonyms
  • Gentiopicroside
  • NSC 606402
Molecular Formula
C16H20O9
Formula Weight
356.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 2 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
210, 245, 271 nm
SMILES
O=C1OCC=C2C1=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2C=C
InChi Code
InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
InChi Key
DUAGQYUORDTXOR-GPQRQXLASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $36

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    25 mg

    $81

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    50 mg

    $153

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    100 mg

    $268

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    Cayman Chemical
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    Product Description

    Gentiopicrin is an iridoid glycoside that has been found in G. rigescens and has diverse biological activities.1,2,3 In vivo, gentiopicrin (130 mg/kg) attenuates acute cholestasis and liver damage and reverses bile acid dyshomeostasis induced by α-napthylisothiocyanate (ANIT) in mice.1 It increases the paw withdrawal threshold in the cold-plate test and latency to paw withdrawal in the plantar test in mice when administered at doses of 25, 50, and 100 mg/kg.2 Gentiopicrin (100 mg/kg) also decreases NMDA receptor-mediated excitatory postsynaptic currents (EPSCs) in the nucleus accumbens and reverses morphine-induced conditioned place preference in mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tang, X., Yang, Q., Yang, F., et al. Target profiling analyses of bile acids in the evaluation of hepatoprotective effect of gentiopicroside on ANIT-induced cholestatic liver injury in mice. J. Ethnaopharmacol. 194, 63-71 (2016).

    2. Liun, N., Li, Y.X., Gong, S.S., et al. Antinociceptive effects of gentiopicroside on neuropathic pain induced by chronic constriction injury in mice: A behavioral and electrophysiological study. Can. J. Physiol. Pharmacol. 94(7), 769-778 (2016).

    3. Liu, S.B., Ma, L., Guo, H.J., et al. Gentiopicroside attenuates morphine rewarding effect through downregulation of GluN2B receptors in nucleus accumbens. CNS Neurosci. Ther. 18(8), 652-658 (2012).