C9617

Carnosol

• Synonym(e): Picrosalvin
• Empirische Formel (Hill-System): C₂₀H₂₆O₄
• CAS-Nummer: 5957-80-2
• Molekulargewicht: 330.42
• NACRES: NA.25
• PubChem Substance ID: 329775081
• UNSPSC Code: 12352100
• MDL number: MFCD02752467

Eigenschaften

• biological source: Rosemarinus officinalis L.
• form: powder
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: CC(C)c1cc2[C@@H]3C[C@H]4C(C)(C)CCC[C@]4(C(=O)O3)c2c(O)c1O
• 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
• InChI key: XUSYGBPHQBWGAD-PJSUUKDQSA-N

Beschreibung

General description

Carnosol (CAR) is an ortho-diphenolic diterpene, extracted from the Mediterranean dietary herb Rosmarinus officinalis L. (rosemary).[1] It was first isolated from the Salvia carnosa (Sage) plant.[1] Carnosol is also a pro-electrophilic molecule.[2]

Application

Carnosol has been used as an anti-cancer agent:

• to test its anti-cancer and anti-proliferative activities on cancer stem-like cells (CSCs)[3] and Glioblastoma multiforme (GBM) cells[3][4]
• to inspect its anti-carcinogenic effects on nineteen genes involved in up-and down-regulation of different genetic carcinogenesis pathways and on HeLa cells in human cervical cancer model
• as a reference standard to identify and quantify the metabolites of rosemary extract using liquid chromatography coupled to tandem mass spectrometry (LC/ESI-MS/MS)[5]

Biochem/physiol Actions

Ein phenolisches Diterpen mit antioxidativen und antikarzinogenen Aktivitäten.

Carnosol together with carnosic acid (CA) accounts for 90% of the antioxidant activity of rosemary leaves.[2] It exerts neuroprotective properties and protects against neuroinflammation[2], and oxidative stress-induced brain damage under chronic stress conditions.[6] Carnosol is a strong chemo-therapeutic agent studied for several types of cancer like breast, leukemia, skin, prostate, and colon.[1][7] It is also an antimicrobial agent.[8]

Sicherheitshinweise

• pictograms: GHS07
• signalword: Warning
• hcodes: H317
• pcodes: P280 - P302 + P352
• Hazard Classifications: Skin Sens. 1
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable