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Geniposide

CAT: 0804-HY-N0009-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N0009-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Geniposide is an iridoid glucoside extracted from Gardenia jasminoidesEllis fruits; exhibits a varity of biological activities such as anti-diabetic, antioxidative, antiproliferative and neuroprotective activities.
CAS Number
24512-63-8
UNSPSC
12352005
Hazard Statement
H301
Target
Amyloid-β; Influenza Virus
Type
Natural Products
Related Pathways
Anti-infection; Neuronal Signaling
Applications
Neuroscience-Neurodegeneration
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/Geniposide.html
Concentration
10mM
Purity
99.72
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : 50 mg/mL (ultrasonic)
Smiles
O[C@@H]1[C@@H](CO)O[C@@H](O[C@H]2[C@@]3([H])[C@@](CC=C3CO)([H])C(C(OC)=O)=CO2)[C@H](O)[C@H]1O
Molecular Formula
C17H24O10
Molecular Weight
388.37
Precautions
H301
References & Citations
[1]Liu H, et al. Fructus Gardenia (Gardenia jasminoides J. Ellis) phytochemistry, pharmacology ofcardiovascular, and safety with the perspective of new drugs development. J Asian Nat Prod Res. 2013;15 (1) :94-110.|[2]Li F, et al. Geniposide attenuates inflammatory response by suppressing P2Y14 receptor and downstream ERK1/2 signaling pathway in oxygen and glucose deprivation-induced brain microvascular endothelial cells. J Ethnopharmacol. 2016 Jun 5;185:77-86.|[3]Wu SY, et al. Effect of geniposide, a hypoglycemic glucoside, on hepatic regulating enzymes in diabetic mice induced by a high-fat diet and streptozotocin. Acta Pharmacol Sin. 2009 Feb;30 (2) :202-8.|[4]Wang J, et al. Geniposide protects against acute alcohol-induced liver injury in mice via up-regulating the expression of the main antioxidant enzymes. Can J Physiol Pharmacol. 2015 Apr;93 (4) :261-7.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Geniposide

Geniposide is a terpene glycoside.

CAS Number24512-63-8
PubChem CID107848
IUPAC Namemethyl (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-tetrahydrocyclopenta[c]pyran-4-carboxylate
Molecular FormulaC17H24O10
Molecular Weight388.4
XLogP-2.3
Topological Polar Surface Area155
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Heavy Atom Count27
Formal Charge0
Complexity617
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
InChI
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
InChIKey
IBFYXTRXDNAPMM-BVTMAQQCSA-N
Chemical Structure
2D Structure
2D structure of Geniposide
CAS: 24512-63-8
CID: 107848
Formula: C17H24O10
MW: 388.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight388.4
XLogP3-2.3
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Exact Mass388.13694696
Monoisotopic Mass388.13694696
Topological Polar Surface Area155 Ų
Heavy Atom Count27
Formal Charge0
Complexity617
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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