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G4796

Genipin

Name: Genipin
Brand: SIGMA

≥98% (HPLC), powder

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Synonym(s):

Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate

Empirical Formula (Hill Notation):

C₁₁H₁₄O₅

CAS Number:

6902-77-8

Molecular Weight:

226.23

MDL number:

MFCD00888600

PubChem Substance ID:

329799931

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: ≥25 mg/mL
H₂O: insoluble

SMILES string

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

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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.

Application

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

Biochem/physiol Actions

Genipin stimulates insulin secretion in UCP2-dependent manner (Uncoupling protein 2). Genipin is a protein, collagen, gelatin, and chitosan cross-linker.

Features and Benefits

This compound is featured on the InsR page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Formation of model hepatocellular aggregates in a hydrogel scaffold using degradable genipin crosslinked gelatin microspheres as cell carriers.

Ting Ting Lau et al.

Biomedical materials (Bristol, England), 7(6), 065003-065003 (2012-11-03)

Primary hepatocyte is probably the preferred cell for cell therapy in liver regeneration. However, its non-ideal proliferation capacity and rapid loss of phenotype during 2D culture compromises the quality and quantity of the transplanted hepatocytes, resulting in variable success rates

Using dairy ingredients to produce edible films and biodegradable packaging materials

Tomasula PM

Dairy-Derived Ingredients: Food and Nutraceutical Uses, 589-624 (2009)

UCP2 expression may represent a predictive marker of neoadjuvant chemotherapy effectiveness for locally advanced uterine cervical cancer

Imai K, et al.

Oncology Letters, 14(1), 951-957 (2017)

Effect of Sulfuric Acid Concentration on Radiological Properties of Genipin Gel Dosimeter

Al-Jarrah A, et al.

International Journal of Chemistry (Canadian Center of Science and Education), 2, 2320-4087 (2014)

Genipin-crosslinked chitosan hydrogels as biomedical and pharmaceutical aids

Muzzarelli RAA

Carbohydrate Polymers, 77(1), 1-9 (2009)

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