AlismoxideCAS# 87701-68-6 |
Quality Control & MSDS
3D structure
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| Cas No. | 87701-68-6 | SDF | Download SDF |
| PubChem ID | 10988340 | Appearance | Oil |
| Formula | C15H26O2 | M.Wt | 238.37 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Synonyms | (+)-Alismoxide | ||
| Solubility | DMSO : ≥ 31 mg/mL (130.05 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (1S,3aR,4R,8aS)-1,4-dimethyl-7-propan-2-yl-2,3,3a,5,6,8a-hexahydroazulene-1,4-diol | ||
| SMILES | CC(C)C1=CC2C(CCC2(C)O)C(CC1)(C)O | ||
| Standard InChIKey | IWQURBSTAIRNAE-BARDWOONSA-N | ||
| 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 | Alismoxide shows an inhibitory effect on the contraction of isolated bladder smooth muscle induced by carbachol; it demonstrates cytostatic action in HeLa cells, revealing potential use in virostatic cocktails. Alismoxide has inhibitory effects on vascular contraction induced by high concentration of KCl; it also shows an inhibitory effect on the direct passive Arthus reaction (DPAR) in rats in the type III allergic model. |
| Targets | NO |
| In vitro | Cytotoxic, cytostatic and HIV-1 PR inhibitory activities of the soft coral Litophyton arboreum.[Pubmed: 24336129]Mar Drugs. 2013 Dec 10;11(12):4917-36.Bioassay-guided fractionation using different chromatographic and spectroscopic techniques in the analysis of the Red Sea soft coral Litophyton arboreum led to the isolation of nine compounds; sarcophytol M (1), alismol (2), 24-methylcholesta-5,24(28)-diene-3β-ol (3), 10-O-methyl Alismoxide (4), Alismoxide (5), (S)-chimyl alcohol (6), 7β-acetoxy-24-methylcholesta-5-24(28)-diene-3,19-diol (7), erythro-N-dodecanoyl-docosasphinga-(4E,8E)-dienine (8), and 24-methylcholesta-5,24 (28)-diene-3β,7β,19-triol (9). |
| In vivo | Studies on Alismatis rhizoma. I. Anti-allergic effects of methanol extract and six terpene components from Alismatis rhizoma (dried rhizome of Alisma orientale).[Pubmed: 9178931]Biol Pharm Bull. 1997 May;20(5):511-6.Methanol and aqueous extracts (TMe-ext and TAq-ext) from dried rhizomes of Alisma orientale have been screened for activity in experimental models of type I-IV allergies. |
| Structure Identification | Chem. Soc. Japan, 1994, 67(5):1394-8.Inhibitory Effects and Active Constituents of Alisma Rhizomes on Vascular Contraction Induced by High Concentration of KCl.[Reference: WebLink]The acetone extract of Alisma rhizomes were found to possess inhibitory effects on vascular contraction induced by high concentration of KCl. Chem Pharm Bull (Tokyo). 1994 Sep;42(9):1813-6.Crude drugs from aquatic plants. IV. On the constituents of alismatis rhizoma. (2). Stereostructures of bioactive sesquiterpenes, alismol, alismoxide, orientalols A, B, and C, from Chinese alismatis rhizoma.[Pubmed: 7954931]
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Alismoxide Dilution Calculator
Alismoxide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.1952 mL | 20.9758 mL | 41.9516 mL | 83.9032 mL | 104.879 mL |
| 5 mM | 0.839 mL | 4.1952 mL | 8.3903 mL | 16.7806 mL | 20.9758 mL |
| 10 mM | 0.4195 mL | 2.0976 mL | 4.1952 mL | 8.3903 mL | 10.4879 mL |
| 50 mM | 0.0839 mL | 0.4195 mL | 0.839 mL | 1.6781 mL | 2.0976 mL |
| 100 mM | 0.042 mL | 0.2098 mL | 0.4195 mL | 0.839 mL | 1.0488 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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Alismoxide is a natural product.
References:
[1]. Blay G, et al. Syntheses of (+)-alismoxide and (+)-4-epi-alismoxide. J Org Chem. 2006 Sep 29;71(20):7866-9.
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Cytotoxic, cytostatic and HIV-1 PR inhibitory activities of the soft coral Litophyton arboreum.[Pubmed:24336129]
Mar Drugs. 2013 Dec 10;11(12):4917-36.
Bioassay-guided fractionation using different chromatographic and spectroscopic techniques in the analysis of the Red Sea soft coral Litophyton arboreum led to the isolation of nine compounds; sarcophytol M (1), alismol (2), 24-methylcholesta-5,24(28)-diene-3beta-ol (3), 10-O-methyl Alismoxide (4), Alismoxide (5), (S)-chimyl alcohol (6), 7beta-acetoxy-24-methylcholesta-5-24(28)-diene-3,19-diol (7), erythro-N-dodecanoyl-docosasphinga-(4E,8E)-dienine (8), and 24-methylcholesta-5,24 (28)-diene-3beta,7beta,19-triol (9). Some of the isolated compounds demonstrated potent cytotoxic- and/or cytostatic activity against HeLa and U937 cancer cell lines and inhibitory activity against HIV-1 protease (PR). Compound 7 was strongly cytotoxic against HeLa cells (CC(5)(0) 4.3 +/- 0.75 microM), with selectivity index of SI 8.1, which was confirmed by real time cell electronic sensing (RT-CES). Compounds 2, 7, and 8 showed strong inhibitory activity against HIV-1 PR at IC(5)(0)s of 7.20 +/- 0.7, 4.85 +/- 0.18, and 4.80 +/- 0.92 microM respectively. In silico docking of most compounds presented comparable scores to that of acetyl pepstatin, a known HIV-1 PR inhibitor. Interestingly, compound 8 showed potent HIV-1 PR inhibitory activity in the absence of cytotoxicity against the cell lines used. In addition, compounds 2 and 5 demonstrated cytostatic action in HeLa cells, revealing potential use in virostatic cocktails. Taken together, data presented here suggest Litophyton arboreum to contain promising compounds for further investigation against the diseases mentioned.
Crude drugs from aquatic plants. IV. On the constituents of alismatis rhizoma. (2). Stereostructures of bioactive sesquiterpenes, alismol, alismoxide, orientalols A, B, and C, from Chinese alismatis rhizoma.[Pubmed:7954931]
Chem Pharm Bull (Tokyo). 1994 Sep;42(9):1813-6.
Following the characterization of the triterpene constituents in Chinese Alismatis Rhizoma, we investigated the chemical structures of orientalols A, B, and C, isolated from the less polar fraction of the crude drug together with two known sesquiterpenes, alismol and Alismoxide. On the basis of the chemical and physicochemical evidence, the structures of orientalols A, B, and C have been determined and those of alismol and Alismoxide were revised. All five sesquiterpenes were found to show an inhibitory effect on the contraction of isolated bladder smooth muscle induced by carbachol.
Studies on Alismatis rhizoma. I. Anti-allergic effects of methanol extract and six terpene components from Alismatis rhizoma (dried rhizome of Alisma orientale).[Pubmed:9178931]
Biol Pharm Bull. 1997 May;20(5):511-6.
Methanol and aqueous extracts (TMe-ext and TAq-ext) from dried rhizomes of Alisma orientale have been screened for activity in experimental models of type I-IV allergies. In the type III allergic model, TMe-ext at oral doses of 50, 200 mg/kg showed an inhibitory effect on the direct passive Arthus reaction (DPAR) in rats, while TAq-ext did not. Four triterpenes (alisol A, alisol B, alisol A monoacetate and alisol B monoacetate) and two sesquiterpenes (alismol and Alismoxide) isolated from TMe-ext also exhibited this inhibitory effect. In a type I allergic model, TMe-ext inhibited 48-h homologous passive cutaneous anaphylaxis (PCA) in rats. In a type II allergic model, it was found that TMe-ext inhibits reversed cutaneous anaphylaxis (RCA) in rats. Furthermore, in a type IV allergic model, TMe-ext had an inhibitory effect on the induction phase in picryl chloride-induced contact dermatitis (PC-CD) in mice. These results indicate that Alismatis Rhizoma not only inhibits antibody-mediated allergic reactions but also influences cell reactions and should be recognized as a material for the treatment of allergic reactions, and the anti-type III allergic components are partially attributable to the terpenes mentioned above.
