12-O-Methylcarnosic acidCAS# 62201-71-2 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 62201-71-2 | SDF | Download SDF |
| PubChem ID | 9974918 | Appearance | White powder |
| Formula | C21H30O4 | M.Wt | 346.46 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Synonyms | Carnosic acid 12-methyl ether; 12-Methoxycarnosic acid | ||
| Solubility | Soluble in chloroform; insoluble in water | ||
| Chemical Name | (4aR,10aS)-5-hydroxy-6-methoxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid | ||
| SMILES | CC(C)C1=C(C(=C2C(=C1)CCC3C2(CCCC3(C)C)C(=O)O)O)OC | ||
| Standard InChIKey | QQNSARJGBPMQDI-YCRPNKLZSA-N | ||
| Standard InChI | InChI=1S/C21H30O4/c1-12(2)14-11-13-7-8-15-20(3,4)9-6-10-21(15,19(23)24)16(13)17(22)18(14)25-5/h11-12,15,22H,6-10H2,1-5H3,(H,23,24)/t15-,21+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. 12-O-Methylcarnosic acid is effective preventing gastric lesions. 2. 12-O-Methylcarnosic acid has antioxidant activity. 3. 12-O-Methylcarnosic acid can suppress melanin production with downregulation of tyrosinase expression in HMV-II melanoma cells. 4. 12-O-Methylcarnosic acid is able to significantly activate peroxisome proliferator-activated receptor (PPAR)γ, it may have anti-diabetic activity. |
| Targets | PPAR |
12-O-Methylcarnosic acid Dilution Calculator
12-O-Methylcarnosic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8863 mL | 14.4317 mL | 28.8634 mL | 57.7267 mL | 72.1584 mL |
| 5 mM | 0.5773 mL | 2.8863 mL | 5.7727 mL | 11.5453 mL | 14.4317 mL |
| 10 mM | 0.2886 mL | 1.4432 mL | 2.8863 mL | 5.7727 mL | 7.2158 mL |
| 50 mM | 0.0577 mL | 0.2886 mL | 0.5773 mL | 1.1545 mL | 1.4432 mL |
| 100 mM | 0.0289 mL | 0.1443 mL | 0.2886 mL | 0.5773 mL | 0.7216 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Gastroprotective effect and cytotoxicity of carnosic acid derivatives.[Pubmed:21246485]
Planta Med. 2011 Jun;77(9):882-7.
Carnosic acid (CA) is the main phenolic diterpene of rosemary (Rosmarinus officinalis L., Lamiaceae) and presents gastroprotective effect in vitro and in vivo. To determine structure-activity relationships, seventeen esters and ethers of CA were prepared, comprising aliphatic, aromatic, and heterocyclic compounds. The naturally occurring 12-O-Methylcarnosic acid (14) was also included in the study. The compounds were evaluated for their gastroprotective activity in the HCl/EtOH-induced gastric lesions model in mice, and for cytotoxicity in human adenocarcinoma AGS cells, Hep G2 hepatocellular carcinoma cells, and human lung fibroblasts. At 10 mg/kg, some of the CA derivatives (5, 8, 9, 12, 14, and 18) were more effective preventing gastric lesions than the reference compound lansoprazole at the same dose. The dibenzoate 9, diindoleacetate 12, and the derivative 18 showed the best gastroprotective effect combined with the lowest cytotoxicity.
Activation of the nuclear receptor PPARgamma by metabolites isolated from sage (Salvia officinalis L.).[Pubmed:20696231]
J Ethnopharmacol. 2010 Oct 28;132(1):127-33.
ETHNOPHARMACOLOGICAL RELEVANCE: Salvia officinalis has been used as a traditional remedy against diabetes in many countries and its glucose-lowering effects have been demonstrated in animal studies. The active compounds and their possible mode of action are still unknown although it has been suggested that diterpenes may be responsible for the anti-diabetic effect of Salvia officinalis. AIM OF THE STUDY: To investigate whether the reported anti-diabetic effects of Salvia officinalis are related to activation of the nuclear receptor peroxisome proliferator-activated receptor (PPAR)gamma and to identify the bioactive constituents. MATERIALS AND METHODS: From a dichloromethane extract of Salvia officinalis able to activate PPARgamma several major metabolites were isolated by chromatographic techniques. To assess bioactivity of the isolated metabolites a PPARgamma transactivation assay was used. RESULTS: Eight diterpenes were isolated and identified including a new abietane diterpene being the epirosmanol ester of 12-O-methyl carnosic acid and 20-hydroxyferruginol, which was isolated from Salvia officinalis for the first time, as well as viridiflorol, oleanolic acid, and alpha-linolenic acid. 12-O-methyl carnosic acid and alpha-linolenic acid were able to significantly activate PPARgamma whereas the remaining metabolites were either unable to activate PPARgamma or yielded insignificant activation. CONCLUSIONS: Selected metabolites from Salvia officinalis were able to activate PPARgamma and hence, the anti-diabetic activity of this plant could in part be mediated through this nuclear receptor.
Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. Antioxidant activity.[Pubmed:12848492]
J Agric Food Chem. 2003 Jul 16;51(15):4247-53.
The distribution of six compounds with three different polyphenol skeletons have been studied in Rosmarinus officinalis: phenolic diterpenes (carnosic acid, carnosol, and 12-O-Methylcarnosic acid), caffeoyl derivatives (rosmarinic acid), and flavones (isoscutellarein 7-O-glucoside and genkwanin), each showing a characteristic behavior and distribution during the vegetative cycle. Only in leaves were all six compounds present, and the highest accumulation rate was related with the young stages of development. Rosmarinic acid showed the highest concentrations of all the polyphenols in all organs. The distribution of this acid in leaves, flowers, and stems suggests that in the first stages of flower growth, levels were due to in situ biosynthesis, and in the last stages, the contribution of transport phenomena was increased. The antioxidant activity of six extracts with different polyphenolic composition was evaluated in aqueous and lipid systems. The results clearly suggest that rosemary extracts are excellent antioxidants in both aqueous and lipid systems.
