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)

Safety Information

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.

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• (1S,4AS,7AS)-7-HYDROXYMETHYL-1-((3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-HYDROXYMETHYL-TETRAHYDRO-PYRAN-2-YLOXY)-1,4A,5,7A-TETRAHYDRO-CYCLOPENTA[C]PYRAN-4-CARBOXYLIC ACID METHYL ESTER