7-O-MethylrosmanolCAS# 113085-62-4 |
- 7beta-Methoxyrosmanol
Catalog No.:BCN7965
CAS No.:24703-38-6
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 113085-62-4 | SDF | Download SDF |
| PubChem ID | 23243692 | Appearance | Powder |
| Formula | C21H28O5 | M.Wt | 360.45 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1R,8S,9S,10S)-3,4-dihydroxy-8-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-trien-15-one | ||
| SMILES | CC(C)C1=C(C(=C2C(=C1)C(C3C4C2(CCCC4(C)C)C(=O)O3)OC)O)O | ||
| Standard InChIKey | XNPVHIQPSAZTLC-NYUBLWNDSA-N | ||
| Standard InChI | InChI=1S/C21H28O5/c1-10(2)11-9-12-13(15(23)14(11)22)21-8-6-7-20(3,4)18(21)17(16(12)25-5)26-19(21)24/h9-10,16-18,22-23H,6-8H2,1-5H3/t16-,17+,18-,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. 7-O-methylrosmanol can effectively suppress FSK-induced luciferase expression under the control of the CRE, PEPCK-C and G6Pase gene promoters, it may contribute to its antihyperglycemic activity. |
| Targets | cAMP |
7-O-Methylrosmanol Dilution Calculator
7-O-Methylrosmanol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7743 mL | 13.8715 mL | 27.7431 mL | 55.4862 mL | 69.3577 mL |
| 5 mM | 0.5549 mL | 2.7743 mL | 5.5486 mL | 11.0972 mL | 13.8715 mL |
| 10 mM | 0.2774 mL | 1.3872 mL | 2.7743 mL | 5.5486 mL | 6.9358 mL |
| 50 mM | 0.0555 mL | 0.2774 mL | 0.5549 mL | 1.1097 mL | 1.3872 mL |
| 100 mM | 0.0277 mL | 0.1387 mL | 0.2774 mL | 0.5549 mL | 0.6936 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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Inhibitory effect of carnosic acid on HIV-1 protease in cell-free assays [corrected].[Pubmed:8229021]
J Nat Prod. 1993 Aug;56(8):1426-30.
In order to find new effective HIV protease inhibitors, two diterpenes (carnosic acid [1] and carnosol [5]) were isolated from rosemary (Rosmarinus officinalis L.), and rosmanol [2] and semisynthetic derivatives (7-O-Methylrosmanol [3], 7-O-ethylrosmanol [4], and 11,12-O,O-dimethylcarnosol [6]) were prepared. The inhibitory activity of all six compounds against HIV-1 protease was tested. The carnosic acid [1] showed the strongest inhibitory effect (IC90 = 0.08 micrograms/ml). The same compound was also assayed against HIV-1 virus replication (IC90 = 0.32 micrograms/ml). The cytotoxic TC90 on H9 lymphocytes was 0.36 micrograms/ml, which is very close to the effective antiviral dose. Additionally, the tested compounds did not inhibit cellular aspartic proteases cathepsin D and pepsin at the concentration range up to 10 micrograms/ml [corrected].
Phenolic diterpenes from rosemary suppress cAMP responsiveness of gluconeogenic gene promoters.[Pubmed:22927089]
Phytother Res. 2013 Jun;27(6):906-10.
The cAMP/protein kinase A/cAMP response element (CRE)-binding protein pathway is important for various physiological aspects including regulation of gluconeogenic gene expression. Rosemary, a well-known herb, has been reported to decrease blood glucose levels. We found that methanol extracts of rosemary suppressed forskolin (FSK)-stimulated luciferase expression under the control of CRE, as well as the promoters for cytosolic phosphoenolpyruvate carboxykinase (PEPCK-C) and glucose-6-phosphatase (G6Pase) catalytic subunit genes in human hepatoma HepG2 cells. Three abietane-type diterpenes and two flavonoids were isolated from the rosemary extracts. Among these, 7-O-Methylrosmanol (1) and royleanonic acid (3) effectively suppressed FSK-induced luciferase expression under the control of the CRE, PEPCK-C and G6Pase gene promoters. PEPCK-C and G6Pase, which play a key role in the homeostatic regulation of blood glucose levels, are important for managing type II diabetes mellitus. Therefore, the ability of rosemary and its components to suppress cAMP responsiveness of the PEPCK-C or G6Pase gene may contribute to its antihyperglycemic activity.
Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone.[Pubmed:19711987]
J Nat Prod. 2009 Aug;72(8):1385-9.
The new aromatic diterpenes 7beta-O-benzylrosmanol (3), 7beta-O-benzyl-11,12-di-O-methylrosmanol (4), and 7alpha-thiophenylcarnosic acid (5) have been obtained by partial synthesis from carnosol (1), an abundant natural diterpene present in Salvia species. The structures of these compounds were established from their physical and spectroscopic data. The known diterpenes sagequinone methide A (6), 7beta-O-methylrosmanol (7), 7-O-Methylrosmanol (8), and rosmaquinone B (9) were obtained from rosmanol (2). The spectroscopic data of these semisynthetic diterpenes were identical to data reported in the literature. In addition, the new semisynthetic isorosmaquinone (10) was obtained from isorosmanol (12). The proton resonances of rosmaquinone (11) are reassigned based on 2D NMR spectroscopy. These compounds, as well as eight known analogues, were evaluated for cytotoxic and antimicrobial activities.
