Genipin
Synonym(s):Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
- CAS NO.:6902-77-8
- Empirical Formula: C11H14O5
- Molecular Weight: 226.23
- MDL number: MFCD00888600
- EINECS: 636-196-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-14 14:09:35
What is Genipin?
Chemical properties
It is a white crystalline powder that is soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from the fruit of Gardenia jasminoides Ellis.
The Uses of Genipin
Genipin is an active aglycone derived from an iridoid glycoside called geniposide, which is found in the fruit of Gardenia jasminoides Ellis. Genipin is a hydrolytic product of geniposide. Genipin has been used in traditional Chinese medicine. Genipin is
The Uses of Genipin
Genipin has been used:
- in chemosensitivity assay
- in the preparation of recombinant human (rh)-odontogenic ameloblast-associated protein (ODAM) -impregnated collagen gel and in vitro mineralization assay
- in genipin gel preparation
What are the applications of Application
Genipin is an anti-inflammatory, anti-angiogenic, cell-permeable inhibitor of uncoupling protein 2 (UCP2).
Definition
ChEBI: Genipin is an iridoid monoterpenoid. It has a role as an uncoupling protein inhibitor, a hepatotoxic agent, an apoptosis inhibitor, an antioxidant, an anti-inflammatory agent and a cross-linking reagent.
General Description
Genipin is a natural cross linking agent, which is extracted from gardenia fruit. It prevents lipid peroxidation and production of nitric oxide. Genipin protects the hippocampal neurons from the toxicity of Alzheimer′s amyloid β protein. It has anti-inflammatory and anti-angiogenesis effects. Genipin is involved in drug delivery system.
Biochem/physiol Actions
Genipin stimulates insulin secretion in UCP2-dependent manner (Uncoupling protein 2). Genipin is a protein, collagen, gelatin, and chitosan cross-linker.
Properties of Genipin
Melting point: | 118.0 to 123.0 °C |
Boiling point: | 287.83°C (rough estimate) |
Density | 1.1230 (rough estimate) |
refractive index | 1.4720 (estimate) |
storage temp. | Inert atmosphere,Room Temperature |
solubility | DMSO: ≥25mg/mL |
form | powder |
pka | 12.06±0.60(Predicted) |
color | White to Almost white |
λmax | 240nm(MeOH)(lit.) |
CAS DataBase Reference | 6902-77-8(CAS DataBase Reference) |
Safety information for Genipin
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral |
Computed Descriptors for Genipin
InChIKey | AZKVWQKMDGGDSV-BCMRRPTOSA-N |
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