GENIPOSIDE

Synonyms. Geniposide; (1S, 4alphaS, 7alpha- 1-(beta-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro- 7-(hydroxymethyl)- cyclopenta[c]pyran-4-carboxylic acid methy ester; Methyl (1S,4aS,7aS)-7- (hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) oxy-1,4a,5,7a- tetrahydro cyclopenta[c]pyran-4-carboxylate;

GENIPOSIDE

Click for original image

 

PRODUCT IDENTIFICATION

CAS RN

24512-63-8

EINECS RN

 

FORMULA

 C17H24O10

MOLE WEIGHT

388.37

H.S CODE

 2938.90.0000

SMILES

 COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H] ([C@ H]([C@@H]([C@H] (O3)CO)O)O)O

CLASSIFICATION

Iridoid

EXTRA NOTES

 Geniposide is an iridoid glycoside with a variety of biological activities including neuroprotective, anti-diabetic, antiproliferative, and antioxidative activity.

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white to off-white crystalline powder

MELTING POINT

160 ~ 164 C

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

 

SOLVENT SOLUBILITY  

VAPOR DENSITY

 

log P(octanol-water)

-1.22

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pH

 

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents.

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 0, Flammability: 0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Google Scholar Search - Geniposide

Drug Information Portal (U.S. National Library of Medicine) - Geniposide

PubChem Compound Summary - Geniposide

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Geniposide

http://www.ebi.ac.uk/ - Geniposide

http://www.ncbi.nlm.nih.gov/ - Geniposide

http://www.sigmaaldrich.com/
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.

www.mdpi.com/
Genipin is the bioactive compound of geniposide and a natural cross-linking agent. In order to improve the preparation process of genipin, the hydrolysis of geniposide to genipin by immobilized β-glucosidase in an aqueous-organic two-phase system was studied. β-Glucosidase was immobilized by the crosslinking-embedding method using sodium alginate as the carrier. The optimum reaction temperature, pH value and time were 55 °C, 4.5 and 2.5 h, respectively. To reduce genipin hydrolysis and byproduct production the reaction was carried out in an aqueous-organic two-phase system comprising ethyl acetate and sodium acetate buffer. The product was analyzed by HPLC, UV, IR, and NMR. The yield of genipin was 47.81% and its purity was over 98% (HPLC). 

 

SALES SPECIFICATION

APPEARANCE

white to off-white crystalline powder

ASSAY

98.0% min

MELTING POINT

160 ~ 164 C
SPECIFIC ROTATION

+13.0° ~ +17.0° (c =1 in EtOH)

HEAVY METALS

10ppm max
RESIDUE ON IGNITION

0.2% max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulates

HAZARD CLASS

  
PACKING GROUP  

 

PACKING