methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

• ChemBase ID: 73271
• Molecular Formular: C11H14O5
• Molecular Mass: 226.22586
• Monoisotopic Mass: 226.08412355
• SMILES: O1C=C([C@@H]2[C@H]([C@@H]1O)C(=CC2)CO)C(=O)OC
• Canonical SMILES: COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate
• IUPAC Traditional name: genipin
• Synonyms: Genipin; Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate; Genipin

Database IDs

• CAS Number: 6902-77-8
• MDL Number: MFCD00888600
• PubChem SID: 162038191
• PubChem CID: 442424
• CHEMBL: 459016
• Chemspider ID: 390864
• KEGG ID: C09780
• Wikipedia Title: Genipin

CALCULATED PROPERTIES

• Acid pKa: 12.036946
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.4438958
• LogD (pH = 7.4): -0.44390568
• Log P: -0.44389567
• Molar Refractivity: 56.0933 cm^3
• Polarizability: 21.838507 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥25 mg/mL; H2O: insoluble
• Apperance: powder

Safety Information

• Storage Condition: -20°C
• RTECS: GY5828000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319
• GHS Precautionary statements: P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C11H14O5

DETAILS

Selleck Chemicals - S2412

Research Area: Metabolic Disease
Biological Activity:
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 used in traditional Chinese medicine to relieve the symptoms of type 2 diabetes. Genipin is an excellent natural cross-linker for proteins, collagen, gelatin, and chitosan cross-linking. Genipin has a low acute toxicity, with LD50 i.v. 382 mg/kg in mice. Therefore, much less toxic than glutaraldehyde and many other commonly used synthetic cross-linking regents. Genipin is also used for pharmaceutical purposes, such as choleretic action for liver diseases control. Furthermore，genipin can be used as a cross-linking agent for immobilized enzyme, the regulating agent for drug delivery, the raw materials for gardenia blue pigment preparation,as well as the intermediate for alkaloid synthetic etc. Genipin is a naturally occurring material that shows great potential as a use in biomaterials and also as a fingerprint reagent. [1][2][3]References on Genipin[1] http://en.wikipedia.org/wiki/Genipin, , [2] Biomaterials. , 2005 Jun, 26(18):3911-8[3] Chang WH et al., 2003, 14(5):481-95

Sigma Aldrich - G4796

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

REFERENCES

• Chen YS et al. Biomaterials. 2005 Jun; 26(18):3911-8.