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SML0153

Sigma-Aldrich

Geniposide

≥98% (HPLC)

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
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

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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 Liu et al.
CNS neuroscience & therapeutics, 18(8), 674-682 (2012-06-26)
Jasminoidin and ursodeoxycholic acid are 2 bioactive compounds extracted from Chinese medicine that have been proven to exert a synergistic effect as a combined administration for the treatment of stroke. The aim of this study was to reveal the pharmacogenomic
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
Mi Jeong Kang et al.
Archives of pharmacal research, 35(4), 733-738 (2012-05-04)
Possible role of metabolism by the intestinal bacteria in geniposide-induced cytotoxicity was investigated in human hepatoma HepG2 cells. Initially, toxic effects of geniposide and its metabolite genipin were compared. Genipin, a deglycosylated form of geniposide, was cytotoxic at the concentrations
Xin-Sheng Wang et al.
Ultrasonics sonochemistry, 19(6), 1155-1159 (2012-05-15)
Fructus gardeniae (Zhizi), one of commonly-used traditional Chinese medicines, is derived from the ripe fruit of the evergreen shrub, Gardenia jasminoides Ellis, and is an ingredient of many traditional Chinese preparations, and has numerous pharmacological actions. Geniposide is the important
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