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SML0153

Geniposide

Name: Geniposide
Brand: SIGMA

≥98% (HPLC), iridoid glycoside, powder

Synonym(s):

(1S,4αS,7αS)- 1-(β-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)- cyclopenta[c]pyran-4-carboxylic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₂₄O₁₀

CAS Number:

24512-63-8

Molecular Weight:

388.37

UNSPSC Code:

12352200

PubChem Substance ID:

329825201

NACRES:

NA.77

MDL number:

MFCD16036219

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Product Name

Geniposide, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H₂O: ≥5 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]3[C@@H]1CC=C3CO

InChI

1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1

InChI key

IBFYXTRXDNAPMM-BVTMAQQCSA-N

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Bioactive Small Molecules

Biochem/physiol Actions

Geniposide is an iridoid glycoside with a variety of biological activities including neuroprotective, anti-diabetic, antiproliferative, and antioxidative activity. Geniposide has been shown to regulate Nrf2 translocation and upregulate downstream antioxidant protein HO-1 expression through the PI3K/Akt signaling pathway, which may account for its neuroprotective and antioxidative activity. Glucagon-like peptide 1 (GLP-1) receptor may also play a critical role in geniposide induced HO-1 expression.

Geniposide is an iridoid glycoside with antioxidative and other biological activities.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000521670

0000344616

0000237508

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Synergism and rules from combination of Baicalin, Jasminoidin and Desoxycholic acid in refined Qing Kai Ling for treat ischemic stroke mice model.

Jian Li et al.

PloS one, 7(9), e45811-e45811 (2012-10-11)

Refined Qing-Kai-Ling (QKL), a modified Chinese medicine, consists of three main ingredients (Baicalin, Jasminoidin and Desoxycholic acid), plays a synergistic effect on the treatment of the acute stage of ischemic stroke. However, the rules of the combination and synergism are

The evaluation and implementation of Direct Analysis in Real Time quadrupole time-of-flight tandem mass spectrometry for characterization and quantification of geniposide in Re Du Ning Injections.

Yan-Jing Li et al.

Rapid communications in mass spectrometry : RCM, 26(11), 1377-1384 (2012-05-05)

The Direct Analysis in Real Time (DART) ionization source coupled with a quadrupole time-of-flight tandem mass spectrometry (Q-TOF MS/MS) system has the capability to desorb analytes directly from samples from complex Chinese herbal preparations without sample cleanup or chromatographic separation.

Glucagon-like peptide 1 receptor plays an essential role in geniposide attenuating lipotoxicity-induced β-cell apoptosis.

Jianhui Liu et al.

Toxicology in vitro : an international journal published in association with BIBRA, 26(7), 1093-1097 (2012-07-24)

β-Cell apoptosis is considered to be a major cause of loss of β cells in diabetes. Geniposide could prevent oxidative stress-induced neuron apoptosis, and improved glucose stimulated insulin secretion by activating glucagon-like peptide 1 receptor (GLP-1R) in INS-1 cells. Here

LPS-induced iNOS expression in N9 microglial cells is suppressed by geniposide via ERK, p38 and nuclear factor-κB signaling pathways.

Gu Zhang et al.

International journal of molecular medicine, 30(3), 561-568 (2012-06-20)

Activated microglia producing reactive nitrogen species, inflammatory factors, reactive oxygen species (ROS) and other neurovirulent factors, can lead to the development of neurodegenerative diseases. Certain compounds can inhibit the activation of microglia. However, the mechanisms remain unclear. In the present

Simple and effective large-scale preparation of geniposide from fruit of Gardenia jasminoides Ellis using a liquid-liquid two-phase extraction.

Min Zhou et al.

Fitoterapia, 83(8), 1558-1561 (2012-09-15)

Geniposide was prepared on a large-scale using a selective two-phase liquid-liquid extraction. The aqueous residue from the fruit of Gardenia jasminoides Ellis was treated with sodium carbonate and extracted with n-butanol several times. The n-butanol extracts were treated with activated

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Global Trade Item Number

SKU	GTIN
SML0153-10MG	04061837076985
SML0153-50MG	04061832723303

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