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Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
enipin · GENIPIN · Jingping · Genipin>GENIPIN(SH) · GENIPIN(RG) · (+)-Genipin · Genipin(AS) · Genipin 95%
![Molekülstruktur von Methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate](/img/chemical/23340.png)
Identifikatoren & physikalische Daten
| CAS No. | 6902-77-8 |
|---|---|
| Summenformel | C11H14O5 |
| Durchschnittliche Molmasse | 226,23 g/mol |
| SMILES | COC(=O)C1=COC(O)C2C(CO)=CCC12 |
| InChIKey | AZKVWQKMDGGDSV-UHFFFAOYSA-N |
| PubChem CID | 23340 |
| ChEBI | CHEBI:94318 |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 76 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 357 |
| Schmelzpunkt | 120 - 121 °C118.0 to 123.0 °C |
| Physical Description | Solid |
| Siedepunkt | 287.83°C (rough estimate) |
| Dichte | 1.1230 (rough estimate) |
| Brechungsindex | 1.4720 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | DMSO: ≥25mg/mL |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 12.06±0.60(Predicted) |
| Farbe | White to Almost white |
| 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 Datenbank | 6902-77-8(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29329990 |
| RTECS-Nr. | GY5828000 |
| R-Sätze (R) | 22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 3/14-36/37/39 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Verwenden
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).