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SML0153

Sigma-Aldrich

Geniposide

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C17H24O10
Numéro CAS:
24512-63-8
Poids moléculaire :
388.37
Numéro MDL:
MFCD16036219
Code UNSPSC :
12352200
ID de substance PubChem :
329825201
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: ≥5 mg/mL

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

IBFYXTRXDNAPMM-BVTMAQQCSA-N

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Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Genipin phyproof® Reference Substance

PHL80458

Genipin

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
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.
Li-xia Guo et al.
Acta pharmacologica Sinica, 33(2), 237-241 (2011-11-22)
To explore the role of the glucagon-like peptide 1 receptor (GLP-1R) in geniposide regulated insulin secretion in rat INS-1 insulinoma cells. Rat INS-1 insulinoma cells were cultured. The content of insulin in the culture medium was measured with ELISA assay.
Tilak Khanal et al.
Toxicology letters, 209(3), 246-254 (2012-01-17)
Intestinal microflora (IM) is able to produce toxic and carcinogenic metabolites and induce more potent cytotoxicity against cells than non-metabolites. This study was performed to investigate the cytotoxic responses of geniposide (GS) and its metabolite and to determine the role
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
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