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6902-77-8

6902-77-8 Structure

6902-77-8 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack 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 InformationBack 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.
Spectrum DetailBack Directory
[Spectrum Detail]

GENIPIN(6902-77-8)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

6902-77-8(sigmaaldrich)
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