5957-80-2

Basic information

• Product Name: CARNOSOL
• Synonyms: CARNOSOL;1,3,4,9,10,10AS-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISO-PROPYL-2H-9S,4AR-(EPOXYMETHANO)PHENANTHREN-12-ONE;1,3,4,9,10AS-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISO-PROPYL-2H-9S,4AR-(EPOXYMETHANO)PHENANTHREN-12-ONE;1,2,3,4,4A,9,10,10AS-OCTAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISOPROPYL-9S, 4AR (EPOXYMETHANO)PHENANTHREN-12-ONE;CARNOSOL(RG);Carnosol, froM RoseMarinus officinalis;Carnosol, 98%, from Rosemarinus officinalis
• CAS NO: 5957-80-2
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.42
• Product Categories: Miscellaneous Natural Products;Antioxidant;Biochemicals Found in Plants;Nutrition Research;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 5957-80-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 240～242℃
• Boiling Point: 524.8 °C at 760 mmHg
• Flash Point: 187 °C
• Appearance: White to beige solid.
• Density: 1.26 g/cm³
• Vapor Pressure: 1.24E-11mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: −20°C
• PKA: 8.91±0.40(Predicted)
• CAS DataBase Reference: CARNOSOL(CAS DataBase Reference)
• NIST Chemistry Reference: CARNOSOL(5957-80-2)
• EPA Substance Registry System: CARNOSOL(5957-80-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 5957-80-2(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 5957-80-2 differently. You can refer to the following data:
1. Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.
2. 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.

Chemical Properties

White powder

Uses

Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.

Cytotoxicity

IC50 (μg/mL): 65 (HL-60), 58 (K562), 50(Hep G2), 48 (MCF-7), 53 (MOLT-4)(Farimani et al. 2012)IC50 (μg/mL): 61.46 (AGS) (Areche et al.2009)IC50 (μg/mL): 2 (P388) (Aoyagi et al.2006)IC50 (μg/mL): 1.19 (A2780), 3.30(SW1573), 8.59 (WiDr), 7.93 (T-47D),1.29 (HBL-100) (Guerrero et al. 2006).

InChI:InChI=1/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-/m1/s1

Upstream product

• 3650-09-7 carnosic acid 

Downstream Products

• 1178895-04-9 7α-thiophenylcarnosic acid 
• 1178895-02-7 7β-O-benzylrosmanol 
• 27210-57-7 miltirone 
• 25460-12-2 11,12-Di-O-methylcarnosol 
• 951125-99-8 6,7-dehydrocarnosic acid 
• 113085-62-4 7α-O-methylrosmanol 
• 1449489-13-7 7α-O-methyl-11,12-seco-11,12-epoxy-11,12-dioxo-8,13-abietadien-20,6β-olide 
• 52591-18-1 galdosol 
• 93380-12-2 epi-rosmanol 

Relevant articles and documents

Preparation method of miltirone

The invention discloses a preparation method of miltirone. The method comprises the following steps: by taking carnosic acid as a raw material, peroxyacid salt or silver oxide as an oxidizing agent and salt formed by a fourth period element as a catalyst, carrying out oxidation reaction to obtain carnosol with high yield; then subjecting the carnosol to a heating reaction under catalysis of formate to obtain the miltirone in one step. The synthesis method disclosed by the invention is simple and convenient to operate and high in yield, avoids using relatively toxic dimethyl sulfate, boron tribromide and trimethylsilyl trifluoromethanesulfonate as reagents, and is suitable for industrial production.

PROCESS FOR PRODUCING CARNOSOL FROM CARNOSIC ACID USING HYDROGEN PEROXIDE OR PERACIDS

Catalytic processes for the production of carnosol from carnosic acid using hydrogen peroxide or a peracid are presented. The carnosic acid may be in pure form, in an impure form, part of a plant extract, or may be present in rosemary needles. The catalyst may be iron, iron salts, a minor amount of water, rosemary needles, or a mixture thereof.

Novel derivatives of carnosic acid

Incubations with Nocardia sp., NRRL 5646 were conducted to produce new derivatives of the abietane-diterpene chemoprotectant and antioxidant, carnosic acid. Reduction of the C-20 carboxylic acid functional group followed by methylation at the C-12 phenol afforded the novel compound 11,20-dihydroxy-12-methoxy-abiet-8,11,13-triene. Oxidative cyclization of carnosic acid to carnosol followed by dihydroxylation at the isopropyl moiety afforded the novel compound 11,12,16,17-tetrahydroxy-7-10-(epoxymethano)-abiet-8,11,13-triene-20-one. The metabolites are new carnosic acid derivatives whose structures were confirmed by mass spectrometry and NMR spectroscopic analysis. The radical quenching properties of the new metabolites using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging assay showed activities improved over that of mixed tocopherols and carnosic acid.