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(R)-(β-D-Glucopyranosyloxy)phenylacetonitril
(r)-prunasin · Prunacin · PRUNASIN · d-prunasin · Noguro Sakura · Wild cherry glycoside · (r)-benzeneacetonitril · Prunasin (6CI, 7CI, 8CI)
Identifikatoren & physikalische Daten
| CAS No. | 99-18-3 |
|---|---|
| Summenformel | C14H17NO6 |
| Durchschnittliche Molmasse | 295,29 g/mol |
| Monoisotopische Masse | 295,10558726 g/mol |
| SMILES | N#C[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccccc1 |
| InChIKey | ZKSZEJFBGODIJW-GMDXDWKASA-N |
| PubChem CID | 119033 |
| ChEMBL | CHEMBL1778417 |
| ChEBI | CHEBI:17396 |
| EC No. | 202-738-0 |
| DTXSID | DTXSID001018995 |
| Lokaler Name | (R)-(β-D-Glucopyranosyloxy)phenylacetonitril |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 123 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 7 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 377 |
| Schmelzpunkt | 147 - 148 °C138-148°C |
| Physical Description | Solid |
| Collision Cross Section | 173.7 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| Siedepunkt | 527.0±50.0 °C(Predicted) |
| Dichte | 1.45±0.1 g/cm3(Predicted) |
| Lagerbedingungen | Hygroscopic, -20°C Freezer, Under Inert Atmosphere |
| Löslichkeit | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 12.71±0.70(Predicted) |
| Farbe | White to off-white |
| Stabilität | Hygroscopic |
| Hauptanwendungen | metabolomicsvitamins, nutraceuticals, and natural products |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChI | InChI=1/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10+,11+,12-,13+,14+/s3 |
| InChIKey | ZKSZEJFBGODIJW-OAWZEMCWNA-N |
| SMILES | O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@H](C1C=CC=CC=1)C#N |&1:1,2,3,5,7,12,r| |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Toxizitätsübersicht | Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1 / PGIII |
| RTECS-Nr. | UL3420000 |
| R-Sätze (R) | 36/37/38-25-60 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 26-36/37/39-61-45 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
(R)-Prunasin is a cyanogenic glucoside that is the precursor to amygdalin, a bitter component found in species of the genera Prunus and Olinia. It can be degraded to hydrogen cyanide, glucose, and benzaldehyde by the action of prunasin hydrolase and mandelonitrile lyase and possesses inhibitory effects on plant growth. (R)-Prunasin reportedly inhibits rat DNA polymerase β, which performs base excision repair required for DNA maintenance and replication, with an IC50 value of 98 μM.
Verwenden
Used in the synthesis of cyanogen glycoside. A component of antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair