An iridoid glycoside with diverse biological activities
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Genipin 1-gentiobioside

Item No. 35621

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,4aS,7aS)-1-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-cyclopenta[c]pyran-4-carboxylic acid, methyl ester
CAS Number
29307-60-6
Synonyms
  • Genipin-1-β-D-gentiobioside
Molecular Formula
C23H34O15
Formula Weight
550.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 5 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
236 nm
SMILES
COC(C1=CO[C@H]([C@@]2([H])[C@]1([H])CC=C2CO)O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O)CO)=O
InChi Code
InChI=1S/C23H34O15/c1-33-20(32)10-6-34-21(13-8(4-24)2-3-9(10)13)38-23-19(31)17(29)15(27)12(37-23)7-35-22-18(30)16(28)14(26)11(5-25)36-22/h2,6,9,11-19,21-31H,3-5,7H2,1H3/t9-,11-,12-,13-,14-,15-,16+,17+,18-,19-,21+,22-,23+/m1/s1
InChi Key
FYZYXYLPBWLLGI-AUOPOVQUSA-N
Origin
Plant/Gardenia jasminoides
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $57

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    1 mg

    $107

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    5 mg

    $390

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    Product Description

    Genipin 1-gentiobioside is an iridoid glycoside that has been found in G. jasminoides and has diverse biological activities.1,2,3 It inhibits acetylcholinesterase (AChE) by 60.23% when used at a concentration of 25 µg/ml.1 Genipin 1-gentiobioside (50-500 µg/ml) is cytotoxic to BRL 3A rat liver fibroblasts.2 It inhibits the germination of G. jasminoides and N. offinicale seeds and the growth of B. rapa roots.3 Genipin 1-gentiobioside (2.5 mg/kg) prevents scopolamine-induced increases in escape latency in the Morris water maze in mice.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kwak, J.H., and Lee, D.-U. Structure–antiamnesic activity relationship of iridoid glycosides from gardenia fruits. Chem. Lett. 44(6), 837-839 (2017).

    2. Li, C., Lan, M., Lv, J., et al. Screening of the hepatotoxic components in Fructus Gardeniae and their effects on rat liver BRL-3A cells. Molecules 24(21), 3920 (2019).

    3. Shimomura, H., Sashida, Y., Nakata, H., et al. Germination and growth inhibitors in fruits of Gardenia jasminoides. Plant Cell Physiol. 24(1), 123-126 (1983).