Genipin

Modify Date: 2024-01-02 16:35:15

Genipin Structure
Genipin structure
 Common Name Genipin
CAS Number 6902-77-8 Molecular Weight 226.226
Density 1.4±0.1 g/cm3 Boiling Point 416.0±45.0 °C at 760 mmHg
Molecular Formula C11H14O5 Melting Point 106-108 °C(lit.)
MSDS Chinese USA Flash Point 164.9±22.2 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Genipin


Genipin is a natural water soluble crosslinking reagent.

 Names

Name Genipin
Synonym More Synonyms

 Genipin Biological Activity

Description Genipin is a natural water soluble crosslinking reagent.
Related Catalog
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

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GY5828000
CHEMICAL NAME :
Cyclopenta(c)pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7- (hydroxymethyl)-, methyl ester
CAS REGISTRY NUMBER :
6902-77-8
LAST UPDATED :
199612
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C11-H14-O5
MOLECULAR WEIGHT :
226.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 19,259,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
237 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 94,157,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
190 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 94,157,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
153 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 94,157,1974

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H319
Precautionary Statements P301 + P310-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn
Risk Phrases 22
Safety Phrases 22
RIDADR UN 2811 6.1/PG 3
RTECS GY5828000
HS Code 2942000000

 Customs

HS Code 2942000000

 Articles31

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 Synonyms

Methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
MFCD00888600
Cyclopenta[c]pyran-4-carboxylic acid, 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester, (1R,4aS,7aS)-
EINECS 300-006-4
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