Genipin

Modify Date: 2025-08-21 02:15:12

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	Signal Word	Danger

Use of Genipin

Genipin is a natural water soluble crosslinking reagent.

Name	Genipin
Synonym	More Synonyms

Description	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.

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

Genipin MSDS(Chinese)

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

Symbol	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

HS Code	2942000000

Dielectric behavior of gelatine-glycosaminoglycans blends: an impedance analysis.

Mater. Sci. Eng. C. Mater. Biol. Appl. 33(4) , 2455-9, (2013)

The dielectric behavior of the gelatine-GAGs based blend systems has been studied to understand the dynamic behavior of the water at the protein-GAGs interfaces which are relevant for tissue engineeri...

Engineered cartilaginous tubes for tracheal tissue replacement via self-assembly and fusion of human mesenchymal stem cell constructs.

Biomaterials 52 , 452-62, (2015)

There is a critical need to engineer a neotrachea because currently there are no long-term treatments for tracheal stenoses affecting large portions of the airway. In this work, a modular tracheal tis...

Genipin crosslinked ethyl cellulose-chitosan complex microspheres for anti-tuberculosis delivery.

Colloids Surf. B Biointerfaces 103 , 530-7, (2013)

Genipin-crosslinked complex microspheres made of the combination of two polymers, ethyl cellulose and chitosan, were prepared by spray drying method. Rifabutin, an anti-tuberculosis agent was used as ...

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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Shanghai Nianxing Industrial Co., Ltd
China
Product Name: Genipin
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DC Chemicals Limited
China
Product Name: Genipin
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ShangHai DC Chemicals Co.,Ltd
China
Product Name: Genipin
Price: ￥Inquiry/1g
Purity: 98.9%
Delivery: 1 Day
Contact: Tony Lai
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Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Genipin
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Delivery: Inquiry
Contact: Ms Wang
Email: enquiry@dycnchem.com

Henan Tianfu Chemical Co., Ltd.
China
Product Name: Genipin
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Delivery: Inquiry
Contact: Anson
Email: info@tianfuchem.com

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Genipin

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HEALTH HAZARD DATA

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