| Identification | More | [Name]
Geniposide | [CAS]
24512-63-8 | [Synonyms]
GENIPOSIDE
Methyl (1R,2S,6S)-9-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
Methyl (1R,2S,6S)-9-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-,methyl ester, (1S,4aS,7aS)-
(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,7aα-tetrahydro-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester
1α-(β-D-Glucopyranosyloxy)-1,4aα,5,7aα-tetrahydro-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid methyl ester | [Molecular Formula]
C17H24O10 | [MDL Number]
MFCD00016659 | [Molecular Weight]
388.37 | [MOL File]
24512-63-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
160.0 to 164.0 °C | [Boiling point ]
641.4±55.0 °C(Predicted) | [density ]
1.54±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
H2O: ≥5mg/mL | [form ]
powder | [pka]
12.80±0.70(Predicted) | [color ]
white to beige | [Detection Methods]
NMR,HPLC | [Stability:]
Hygroscopic | [InChIKey]
IBFYXTRXDNAPMM-BWBTYKGONA-N | [SMILES]
C12C(CO)=CCC1C(C(=O)OC)=CO[C@H]2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O |&1:14,16,17,19,20,22,r| | [LogP]
-1.920 (est) | [CAS DataBase Reference]
24512-63-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
Geniposide is an iridoid glycoside isolated from the fruit of Gardenia jasminoides Ellis. Geniposide is one of the biologically active ingredients of gardenia fruit. Geniposide is widely used in multi-component injection in the treatment of cerebrovascula | [Definition]
ChEBI: Geniposide is a terpene glycoside. | [General Description]
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG | [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. |
| Questions And Answer | Back Directory | [Pharmacological effects]
Geniposide, also known as Gardenia glycosides, geniposide. It is a brown to white crystalline powder, with little flavor and no bitter taste, a cycloolefin ether glycoside compound extracted from the dry and ripe fruit of Rubiaceae Gardenia. Geniposide has a significant role in promoting bile secretion, and can reduce blood bilirubin, as well as promote rapid excretion of bilirubin in the blood. It has an inhibitory effect on Streptococcus hemolyticus and skin fungi. It also has antipyretic, analgesic, sedative, antihypertensive and hemostatic effects. Geniposide has the function of purging pathogenic fire and eliminating restlessness, clearing heat and eliminating damp, decreasing swellinging to relieving pain. The Indications of Geniposide are heat disease, dysphoria, coma delirium, jaundice, heat stranguria, heat in blood, swelling and pain of eye, pathopyretic ulcer, and sprain. |
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