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| | Genipin Basic information |
| Product Name: | Genipin | | Synonyms: | Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate;cyclopenta(c)pyran-4-carboxylicacid,1,4a-alpha,5,7a-alpha-tetrahydro-1-hydrox;GENIPIN;1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester;Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate;(1R)-1,4aα,5,7aα-Tetrahydro-1-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;(1R)-1,4aα,5,7aα-Tetrahydro-1α-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;enipin | | CAS: | 6902-77-8 | | MF: | C11H14O5 | | MW: | 226.23 | | EINECS: | 636-196-5 | | Product Categories: | Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract | | Mol File: | 6902-77-8.mol |  |
| | Genipin Chemical Properties |
| 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.) | | InChI | InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1 | | InChIKey | AZKVWQKMDGGDSV-BCMRRPTOSA-N | | SMILES | [C@@H]1(O)OC=C(C(OC)=O)[C@@]2([H])CC=C(CO)[C@@]12[H] | | CAS DataBase Reference | 6902-77-8(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 3/14-36/37/39 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | RTECS | GY5828000 | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29329990 |
| | Genipin Usage And Synthesis |
| 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. | | Uses | Genipin is an active aglycone derived from geniposide, an iridoid glycoside found in the fruit of Gardenia jasminoides Ellis. It has been used in traditional Chinese medicine and is a hydrolytic product of geniposide. Genipin is also known for its inhibitory effect on uncoupling protein 2 (UCP2). | | Uses | 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
| | 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. |
| | Genipin Preparation Products And Raw materials |
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