CAS Number6902-77-8
SynonymsMethyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate; MFCD00888600; EINECS 300-006-4
Molecular FormulaC11H14O5
Molecular Weight226.23
Purity≥98 (HPLC)%
Density1.4±0.1 g/cm3
Boiling Point416.0±45.0 °C at 760 mmHg
Melting Point106-108 °C(lit.)
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 6902-77-8 |
| Catalog No. | 2A-9010710 |
| Chinese Name | 京尼平 |
| Synonyms | Methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate; MFCD00888600; EINECS 300-006-4 |
| Molecular Formula | C11H14O5 |
| Molecular Weight | 226.23 |
| Purity | ≥98 (HPLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 416.0±45.0 °C at 760 mmHg |
| Melting Point | 106-108 °C(lit.) |
| Appearance | powder |
| Storage Condition | Room Temperature |
| Application | Genipin is a natural water-soluble cross-linking agent. |
| HTC | 2942000000 |
| PubChem ID | 329799931 |
| MDL Number | MFCD00888600 |
| SMILES | COC(=O)C1=CO[C@@H](O)C2C1CC=C2CO |
| 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 |
| InChI Key | AZKVWQKMDGGDSV-BCMRRPTOSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/10710_1_6902_77_8.pdf |
| Bioactivity | Genipin is a natural water soluble crosslinking reagent. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Metabolic Disease Natural Products >> Terpenoids and Glycosides In Vitro Genipin stimulats glucose uptake in a time- and dose-dependent manner. The maximal effect is achieved at 2 h with a concentration of 10 μM. In myotubes, genipin promotes glucose transporter 4 (GLUT4) translocation to the cell surface, which increases the phosphorylation of insulin receptor substrate-1 (IRS-1), AKT, and GSK3β. Meanwhile, genipin increases ATP levels, closed KATP channels, and then increases the concentration of calcium in the cytoplasm in C2C12 myotubes. Genipin-stimulated glucose uptake could be blocked by both the PI3-K inhibitor wortmannin and calcium chelator EGTA. Moreover, genipin increases the level of reactive oxygen species and ATP in C2C12 myotubes[1]. Genipin increases mitochondrial membrane potential, which then increases ATP levels and closes KATP channels, thereby stimulating insulin secretion in pancreatic β-cells. Genipin activates glucose-excited POMC neurons[2]. Cytochrome c content increases significantly in the cytosol of genipin-treated FaO cells. Activation of caspase-3 and caspase-7 is ultimately responsible for genipin-induced apoptotic process in hepatoma cells. ROS level notably increases in Hep3B cells treated with 200 μM genipin[3]. Kinase Assay Briefly, the peptide substrate N-acetyl-Asp-Glu-Val-Asp-ρ-nitroanilide (Ac-DEVD-ρNA) is added to the cell lysates in assay buffer (50 mM HEPES, pH 7.4, 100 mM NaCl, 0.1% CHAPS, 10 mM dithiothreitol, 1 mM EDTA, 10% glycerol) and incubated at 37°C. The cleavage of the substrate is monitored at 405 nm. References [1]. Ma C, et al. Genipin stimulates glucose transport in C2C12 myotubes via IRS-1 and calcium- dependent mechanism. J Endocrinol. 2012 Dec 20. [2]. Parton LE, et al. Glucose sensing by POMC neurons regulates glucose homeostasis and is impaired in obesity. Nature. 2007 Sep 13;449(7159):228-32. [3]. Kim BC, et al. Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway. Biochem Pharmacol. 2005 Nov 1;70(9):1398-407. [4]. Ye D, et al. Genipin normalizes depression-like behavior induced by prenatal stress through inhibiting DNMT1. Epigenetics. 2018 Mar 9:1-22. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 416.0±45.0 °C at 760 mmHg Melting Point 106-108 °C(lit.) Molecular Formula C11H14O5 Molecular Weight 226.226 Flash Point 164.9±22.2 °C Exact Mass 226.084122 PSA 75.99000 LogP 0.12 Vapour Pressure 0.0±2.2 mmHg at 25°C Index of Refraction 1.565 InChIKey AZKVWQKMDGGDSV-BCMRRPTOSA-N SMILES COC(=O)C1=COC(O)C2C(CO)=CCC12 |
| Use of | Genipin is a natural water soluble crosslinking reagent. Properties Articles31 Name Genipin Synonym More Synonyms Genipin Biological Activity Description Genipin is a natural water soluble crosslinking reagent. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Metabolic Disease Natural Products >> Terpenoids and Glycosides References [2]. Parton LE, et al. Glucose sensing by POMC neurons regulates glucose homeostasis and is impaired in obesity. Nature. 2007 Sep 13;449(7159):228-32. [3]. Kim BC, et al. Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway. Biochem Pharmacol. 2005 Nov 1;70(9):1398-407. [4]. Ye D, et al. Genipin normalizes depression-like behavior induced by prenatal stress through inhibiting DNMT1. Epigenetics. 2018 Mar 9:1-22. Chemical & Physical Properties Molecular Formula C11H14O5 Exact Mass 226.084122 PSA 75.99000 Index of Refraction 1.565 InChIKey AZKVWQKMDGGDSV-BCMRRPTOSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Dangerous Regulations for land transport: 2811 International Dangerous Regulations for sea transport: 2811 International Dangerous Regulations for air transport: 2811 14.2 United Nations shipping name European Land Transport Dangerous Regulations: TOXIC SOLID, ORGANIC, N.O.S. (Genipin) IMDG: TOXIC SOLID, ORGANIC, N.O.S. (Genipin) International air transport hazard regulations: Toxic solid, organic, n.o.s. (Genipin) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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