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SML0153

Sigma-Aldrich

Geniposide

≥98% (HPLC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C17H24O10
Número de CAS:
24512-63-8
Peso molecular:
388.37
MDL number:
MFCD16036219
UNSPSC Code:
12352200
PubChem Substance ID:
329825201
NACRES:
NA.77

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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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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
K Hiramatsu et al.
Alimentary pharmacology & therapeutics, 36(6), 575-586 (2012-07-24)
Idiopathic mesenteric phlebosclerosis (IMP) is a rare disease, characterised by thickening of the wall of the right hemicolon with calcification of mesenteric veins. However, the aetiology remains unknown. To investigate the possible association of herbal medicines with IMP. The clinical
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
Jinhong Liu et al.
Aging, 12(22), 22744-22758 (2020-11-17)
Acute kidney injury is one of the most common complications that occurs in septic shock. An effective therapeutic intervention is urgently needed. Geniposide has been reported to possess pleiotropic activities against different diseases. However, the effect of geniposide on sepsis-induced
Jun Wang et al.
Neurochemical research, 37(10), 2235-2248 (2012-08-08)
Geniposide, an iridoid glycoside isolated from Gardenia, has neuroprotective activities against oxidative stress and inflammation. The present study investigated the in vivo protective effect of geniposide on ischemia/reperfusion-injured rats by middle cerebral artery occlusion (MCAO), and the inhibitory effects of
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