(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
carnol · CARNOSOL · BCL6-IN-13 · D-α-Alanine · Carnosol-RM · CARNOSOL(RG) · CARNOSOL USP/EP/BP · Carnosol (Standard)
![Molekülstruktur von (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one](/img/chemical/2579.png)
Identifikatoren & physikalische Daten
| CAS No. | 5957-80-2 |
|---|---|
| Summenformel | C20H26O4 |
| Durchschnittliche Molmasse | 330,4 g/mol |
| Monoisotopische Masse | 330,18310931 g/mol |
| SMILES | CC(C)c1cc2c(c(O)c1O)C13CCCC(C)(C)C1CC2OC3=O |
| InChIKey | XUSYGBPHQBWGAD-UHFFFAOYSA-N |
| PubChem CID | 2579 |
Chemische & physikalische Eigenschaften
| XLogP | 4,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 66,8 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 24 |
| Formalladung | 0 |
| Komplexität | 542 |
| Schmelzpunkt | 240~242℃ |
| Siedepunkt | 524.8±50.0 °C(Predicted) |
| Dichte | 1.26±0.1 g/cm3(Predicted) |
| Lagerbedingungen | Sealed in dry,Store in freezer, under -20°C |
| Löslichkeit | DMSO:66.0(Max Conc. mg/mL)199.74(Max Conc. mM) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 8.91±0.40(Predicted) |
| Farbe | White |
| Biologische Quelle | Rosemarinus officinalis L. leaves |
| Hauptanwendungen | food and beverages |
| InChI | InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1 |
| InChIKey | XUSYGBPHQBWGAD-PJSUUKDQSA-N |
| SMILES | C1(C)(C)[C@@]2([H])[C@]3(C(=O)O[C@@]([H])(C2)C2=C3C(O)=C(O)C(C(C)C)=C2)CCC1 |
| LogP (Verteilungskoeffizient) | 2.832 (est) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| Zollcode | 29322090 |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 5957-80-2(Hazardous Substances Data) |
| Gefahrenklasse | Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
Carnosol is a phenol that has been found in rosemary (R. officinalis) and has diverse biological activities. It decreases nitric oxide (NO) production in mouse peritoneal exudate macrophages when used at concentrations ranging from 6 to 25 μM. Carnosol scavenges peroxyl and hydroxyl radicals and inhibits lipid peroxidation in cell-free assays. It inhibits 5-lipoxygenase (5-LO; IC50 = 0.1 μM for the recombinant human enzyme) and the synthesis of leukotrienes in human polymorphonuclear leukocytes (PMNs; IC50 = 7 μM). In vivo, carnosol (200 mg/kg) reduces mammary DNA adduct formation and tumorigenesis in a rat model of DMBA-induced mammary tumorigenesis.
Verwenden
Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.