5957-80-2

Usage

Uses

Used in Anticancer Applications:
Carnosol is used as an anticarcinogen for its ability to reduce mammary DNA adduct formation and tumorigenesis in a rat model of DMBA-induced mammary tumorigenesis. It functions as a potent chemopreventive agent, protecting cells from the harmful effects of carcinogens and reducing the risk of cancer development.
Used in Pharmaceutical Industry:
Carnosol is used as an antioxidant for its ability to scavenge peroxyl and hydroxyl radicals, as well as inhibit lipid peroxidation in cell-free assays. This makes it a valuable compound for the development of pharmaceutical products aimed at preventing and treating various diseases associated with oxidative stress.
Used in Food Industry:
Carnosol is used as a natural preservative for its antimicrobial properties. It can help extend the shelf life of food products by inhibiting the growth of harmful microorganisms, ensuring the safety and quality of the products.
Used in Cosmetics Industry:
Carnosol is used as an active ingredient in cosmetics for its antioxidant and anti-aging properties. It can help protect the skin from environmental stressors, such as free radicals and UV radiation, and promote a healthier, more youthful appearance.
Used in Nutraceutical Industry:
Carnosol is used as a dietary supplement for its various health-promoting properties, including its antioxidant, antimicrobial, and anticarcinogenic activities. It can be incorporated into nutraceutical products to support overall health and well-being.

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

• 450410-87-4 11,12-O-didehydrocarnosol 
• 475654-77-4 11,12-seco-11,12-epoxy-11,12-dioxo-8,13-abietadien-20,7β-olide 
• 1449489-13-7 7α-O-methyl-11,12-seco-11,12-epoxy-11,12-dioxo-8,13-abietadien-20,6β-olide 
• 113085-62-4 7α-O-methylrosmanol 
• 27210-57-7 miltirone 
• 25460-12-2 11,12-Di-O-methylcarnosol 
• 951125-99-8 6,7-dehydrocarnosic acid 
• 1178895-02-7 7β-O-benzylrosmanol 
• 1178895-04-9 7α-thiophenylcarnosic acid 

Relevant academic research and scientific papers

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.

Syntheses of carnosic acid and carnosol, anti-oxidants in rosemary, from pisiferic acid, the major constituent of Sawara

Carnosic acid (2), a major anti-oxidant in rosemary (Rosmarinus officinalis), was synthesized from pisiferic acid (1), the major constituent of Sawara (Chamaecyparis pisifera), via ortho-oxidation of the phenol using metachlorobenzoyl peroxide (mCBPO), chloroacetyl meta-chlorobenzoyl peroxide (CAMCBPO) or 2-iodoxybenzoic acid (IBX). Carnosol (3), another anti-oxidant in rosemary, was synthesized from carnosic acid by oxidation with silver oxide. Potent antibacterial activities against Propionibacterium acnes (ATCC 6919) (minimum inhibitory concentration (MIC) μg/ml) and Staphylococcus aureus ME/GM/TC Resistant (ATCC 33592) (MIC μg/ml) of carnosic acid and carnosol were reported.

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.

PROCESS FOR PRODUCING CARNOSOL FROM CARNOSIC ACID

Catalytic processes for the production of carnosol from carnosic acid 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 needeles, 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.

Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities

The known diterpenes rosmanoi (3), rosmaquinone (4), 7-methoxyrosmanol (5), 7-ethoxyrosmanol (6), galdosol (7), and epirosmanol (8) have been obtained by partial synthesis from carnosol (2), an abundant natural product present in Salvia species. The physical and spectroscopic data of these semisynthetic diterpenes were identical to those of authentic natural samples and with data reported in the literature. These abietane diterpenes have very interesting biological activities and are present in the genus Salvia in low quantities; thus, the semisynthetic approach described here represents an efficient alternative method to obtain these compounds. Additionally, the known diterpene 16-hydroxyrosmanol (10) and a new aromatic diterpene 11 were obtained from 16-hydroxycarnosol (9) by reaction with Ph3P/NBS in CH2Cl2. The structure of the new compound 11 was established from its spectroscopic data as 12,16-epoxycarnosol.