Cyclandelat
3,3,5-TRIMETHYLCYCLOHEXYL MANDELATE · bs572 · Cydel · Natil · andeL · BS 572 · Capilan · Anaspat
Identifikatoren & physikalische Daten
| CAS No. | 456-59-7 |
|---|---|
| Summenformel | C17H24O3 |
| Durchschnittliche Molmasse | 276,4 g/mol |
| Monoisotopische Masse | 276,17254462 g/mol |
| SMILES | CC1CC(OC(=O)C(O)c2ccccc2)CC(C)(C)C1 |
| InChIKey | WZHCOOQXZCIUNC-UHFFFAOYSA-N |
| PubChem CID | 2893 |
| ChEMBL | CHEMBL1480987 |
| ChEBI | CHEBI:3988 |
| EC No. | 207-271-6 |
| DTXSID | DTXSID4022862 |
| Lokaler Name | Cyclandelat |
Chemische & physikalische Eigenschaften
| XLogP | 4,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 331 |
| Color/Form | CRYSTALS |
| Löslichkeit | PRACTICALLY INSOL IN WATERSOL IN LIPOIDS & THEIR SOLVENTSFREELY SOL IN PETROLEUM ETHER, ETHANOLSOL IN DIETHYL ETHER, ACETONE9.97e-02 g/LInsoluble in waterChloroform (Slightly), Methanol (Slightly, Sonicated) |
| Siedepunkt | 192-194 °C @ 14 MM HGbp14 192-194° |
| Schmelzpunkt | 50-5350-53 °C56 °C55.0-56.5° |
| Physical Description | Solid |
| Collision Cross Section | 186.2 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]184.48 Ų [M+Na]+ [CCS Type: TW |
| Dichte | 1.0535 (rough estimate) |
| Brechungsindex | 1.5490 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | powder to crystal |
| pKa (Säurekonstante) | 12.13±0.20(Predicted) |
| Farbe | White to Almost white |
| Merck | 14,2704 |
| InChI | InChI=1S/C17H24O3/c1-12-9-14(11-17(2,3)10-12)20-16(19)15(18)13-7-5-4-6-8-13/h4-8,12,14-15,18H,9-11H2,1-3H3 |
| InChIKey | WZHCOOQXZCIUNC-UHFFFAOYSA-N |
| SMILES | C1(CC(CC(C)(C)C1)C)OC(=O)C(O)C1C=CC=CC=1 |
| EPA chemische Informationen | Benzeneacetic acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl ester (456-59-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH319 (97.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Eye Irrit. 2 (97.5%) |
| Human Toxicity Excerpts | CYCLANDELATE APPEARS TO PRODUCE LITTLE SERIOUS TOXICITY. HOWEVER, ORAL DOSES OF 200 MG OR MORE ARE ASSOC WITH SIGNIFICANT INCIDENCE OF UNPLEASANT SIDE EFFECTS, INCL GASTROINTESTINAL UPSETS, FLUSHING, TINGLING, HEADACHE, DIZZINESS, & SWEATING.SIDE EFFECTS INCLUDE...NAUSEA...& HYPOTENSION....IT HAS BEEN CLAIMED THAT CYCLANDELATE REDUCED OPHTHALMIC BLOOD PRESSURE BUT INCR FLOW IN RETINAL ARTERIES. IT APPEARS THAT CYCLANDELATE PRESENTS NO SIGNIFICANT THREAT OF RAISING OCULAR PRESSURE IN OPEN-ANGLE GLAUCOMA NOR ANY THREAT OF PRECIPITATING ANGLE-CLOSURE GLAUCOMA... |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2918191350 |
| RTECS-Nr. | OO8200000 |
| Toxizität | LD50 oral in rat: 5gm/kg |
| Gefahrstoffdaten | 456-59-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Almond (Amygdalus communis L) is a kind of nut from Xinjiang, China. Traditional Chinese medicine believes that almond can promote blood circulation to dispel blood stasis, lubricate bowels to relieve constipation, and relieve cough and asthma. The indications include amenorrhea, fever, wind arthralgia, malaria, blood stasis and pain, injuries, and blood stasis with constipation.
History
The chemical synthesis of cyclandelate was first synthesized by Funcke et al. from Elan Corporation in Ireland using a-hydroxyphenylacetic acid and cis-3,3,5-cycloalkyl cyclohexanol. The raw material of mandelic acid was obtained by hydrolysis after benzaldehyde reacted to sodium cyanide. However, sodium cyanide is hypertoxic, and because of its unique structure of a-hydroxy acid, it is easy to decompose under the acid condition, which leads to more by-products and low yield. A series of improved methods have been developed, which can reduce the environmental pollution under the premise of ensuring the yield of Zn/HCOONH4/ C2H5OH system . The method was used to synthesize cyclandelate since then. However, this drug has not yet been approved by the Food and Drug Administration in the United States, Canada, and other countries because it easily causes white blood cell deficiency. It has been withdrawn from the market after drug approval in Japan, France, and other countries in the 1970s.
Verwenden
vasodilator