Imbricatolic acidCAS# 6832-60-6 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 6832-60-6 | SDF | Download SDF |
| PubChem ID | 70688370 | Appearance | Powder |
| Formula | C20H34O3 | M.Wt | 322.5 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1S,4aR,5S,8aR)-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid | ||
| SMILES | CC(CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C)CCO | ||
| Standard InChIKey | NSRKLZRKJJQJLD-BEUFEYIVSA-N | ||
| Standard InChI | InChI=1S/C20H34O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h14,16-17,21H,2,5-13H2,1,3-4H3,(H,22,23)/t14-,16-,17+,19+,20-/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. Imbricatolic acid can prevent cell cycle progression in p53-null CaLu-6 cells. |
| Targets | p53 |
Imbricatolic acid Dilution Calculator
Imbricatolic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.1008 mL | 15.5039 mL | 31.0078 mL | 62.0155 mL | 77.5194 mL |
| 5 mM | 0.6202 mL | 3.1008 mL | 6.2016 mL | 12.4031 mL | 15.5039 mL |
| 10 mM | 0.3101 mL | 1.5504 mL | 3.1008 mL | 6.2016 mL | 7.7519 mL |
| 50 mM | 0.062 mL | 0.3101 mL | 0.6202 mL | 1.2403 mL | 1.5504 mL |
| 100 mM | 0.031 mL | 0.155 mL | 0.3101 mL | 0.6202 mL | 0.7752 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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Synthesis of novel imbricatolic acid analogues via insertion of N-substituted piperazine at C-15/C-19 positions, displaying glucose uptake stimulation in L6 skeletal muscle cells.[Pubmed:22726926]
Bioorg Med Chem Lett. 2012 Jul 15;22(14):4636-9.
A new class of N-substituted piperazine analogues of Imbricatolic acid have been designed and synthesized by using the appropriate synthetic routes in excellent yield. All synthesised compounds were screened for their in vitro glucose uptake stimulatory activity. Among them compounds 4b, 4e, 8b, and 8e triggered L6 skeletal muscle cells for glucose uptake at 54.73%, 40.79%, 40.90%, and 39.55% stimulation, respectively. Compound 4b has emerged as important lead compound showing potential antidiabetic activity. Illustration about their synthesis and in vitro glucose uptake activity is described.
Imbricatolic acid from Juniperus communis L. prevents cell cycle progression in CaLu-6 cells.[Pubmed:21567359]
Planta Med. 2011 Nov;77(16):1822-8.
Imbricatolic acid was isolated from the methanolic extract of the fresh ripe berries of Juniperus communis (Cupressaceae) together with sixteen known compounds and a new dihydrobenzofuran lignan glycoside named juniperoside A. Their structures were determined by spectroscopic methods and by comparison with the spectral data reported in literature. Imbricatolic acid was evaluated for its ability to prevent cell cycle progression in p53-null CaLu-6 cells. This compound induces the upregulation of cyclin-dependent kinase inhibitors and their accumulation in the G1 phase of the cell cycle, as well as the degradation of cyclins A, D1, and E1. Furthermore, no significant Imbricatolic acid-induced apoptosis was observed. Therefore, this plant-derived compound may play a role in the control of cell cycle.
Biotransformations of imbricatolic acid by Aspergillus niger and Rhizopus nigricans cultures.[Pubmed:17873843]
Molecules. 2007 May 21;12(5):1092-100.
Microbial transformation of Imbricatolic acid (1) by Aspergillus niger afforded 1alpha-hydroxyImbricatolic acid (2), while transformation with Rhizopus nigricans yielded 15-hydroxy-8,17-epoxylabdan-19-oic acid (3). When the diterpene 1 was added to a Cunninghamella echinulata culture, the main products were the microbial metabolites mycophenolic acid (4) and its 3-hydroxy derivative 5. All the structures were elucidated by spectroscopic methods. The cytotoxicity of these compounds towards human lung fibroblasts and AGS cells was assessed. While 4 and 5 showed low cytotoxicity, with IC50 values > 1000 microM against AGS cells and fibroblasts, 1alpha-hydroxyImbricatolic acid (2) presented moderate toxicity towards these targets, with IC50 values of 307 and 631 microM, respectively. The structure of 2 is presented for the first time.
