| Identification | More | [Name]
1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester | [CAS]
6902-77-8 | [Synonyms]
1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester
GENIPIN
cyclopenta(c)pyran-4-carboxylicacid,1,4a-alpha,5,7a-alpha-tetrahydro-1-hydrox
Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
(1R)-1,4aα,5,7aα-Tetrahydro-1-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester
(1R)-1,4aα,5,7aα-Tetrahydro-1α-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester | [EINECS(EC#)]
636-196-5 | [Molecular Formula]
C11H14O5 | [MDL Number]
MFCD00888600 | [Molecular Weight]
226.23 | [MOL File]
6902-77-8.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [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 |
| Hazard Information | Back Directory | [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 an iridoid glycoside called geniposide, which is found in the fruit of Gardenia jasminoides Ellis. Genipin is a hydrolytic product of geniposide. Genipin has been used in traditional Chinese medicine. Genipin is | [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(6902-77-8) 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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