Alphitolic acidCAS# 19533-92-7 |
Quality Control & MSDS
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| Cas No. | 19533-92-7 | SDF | Download SDF |
| PubChem ID | 12305768 | Appearance | Powder |
| Formula | C30H48O4 | M.Wt | 472.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Synonyms | 2alpha-Hydroxybetulinic acid | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1R,3aS,5aR,5bR,7aR,9R,10R,11aR,11bR,13aR,13bR)-9,10-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid | ||
| SMILES | CC(=C)C1CCC2(C1C3CCC4C(C3(CC2)C)(CCC5C4(CC(C(C5(C)C)O)O)C)C)C(=O)O | ||
| Standard InChIKey | PFCVZKFJHRCLCC-PGOIBATFSA-N | ||
| Standard InChI | InChI=1S/C30H48O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h18-24,31-32H,1,8-16H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22+,23+,24-,27-,28+,29+,30-/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. Alphitolic acid is an anti-inflammatory triterpene, has antitumour activity in oral squamous cell carcinoma (OSCC) cells. 2. Alphitolic acid can suppress the proliferation of SCC4 and SCC2095 OSCC cells with IC50 values of 12 and 15 uM, respectively, via apoptotic induction, this drug effect on apoptosis is, in part, associated with its ability to block Akt-NF-κB signalling; it could as an ingredient in functional food/dietary supplement for OSCC prevention. 3. Alphitolic acid is a potent Hh/GLI signaling inhibitor, it shows an important relationship between Hh/GLI signaling inhibition, the decrease of BCL2, and cytotoxicity against cancer cells. 4. Alphitolic acid shows antimicrobial activity on Gram-positive bacteria and yeasts. 5. Alphitolic acid can inhibit NO release and iNOS expression in LPS-stimulated J774.A1 cultured macrophages. |
| Targets | Akt | NF-kB | p53 | Bcl-2/Bax | Antifection |
Alphitolic acid Dilution Calculator
Alphitolic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1155 mL | 10.5775 mL | 21.1551 mL | 42.3101 mL | 52.8877 mL |
| 5 mM | 0.4231 mL | 2.1155 mL | 4.231 mL | 8.462 mL | 10.5775 mL |
| 10 mM | 0.2116 mL | 1.0578 mL | 2.1155 mL | 4.231 mL | 5.2888 mL |
| 50 mM | 0.0423 mL | 0.2116 mL | 0.4231 mL | 0.8462 mL | 1.0578 mL |
| 100 mM | 0.0212 mL | 0.1058 mL | 0.2116 mL | 0.4231 mL | 0.5289 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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Antimicrobial triterpenoids from Licania heteromorpha.[Pubmed:11199141]
Planta Med. 2000 Dec;66(8):768-9.
Six triterpenoids having a lupane and oleane skeleton were isolated from the leaves and young branches of Licania heteromorpha Bentham var. heteromorpha and were identified as: betulinic acid 1, Alphitolic acid 2, 3 beta-O-trans-p-coumaroyl Alphitolic acid 3, 3 beta-O-cis-p-coumaroyl Alphitolic acid 4, 3 beta-O-trans-p-coumaroyl maslinic acid 5, 3 beta-O-cis-p-coumaroyl maslinic acid 6. The antimicrobial activity of these compounds was evaluated in vitro on clinically isolated microorganisms employing a microdilution method. Compounds 2, 3, 5, and 6 showed antimicrobial activity on Gram-positive bacteria and yeasts, whereas none of the six triterpenoids were active against Gram-negative organisms.
Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.[Pubmed:18842418]
Bioorg Med Chem. 2008 Nov 1;16(21):9420-4.
The aberrant hedgehog (Hh)/GLI signaling pathway causes the formation and progression of a variety of tumors. By screening tropical plant extracts by using our screening system, Zizyphus cambodiana was found to include Hh/GLI signaling inhibitors. Bioassay-guided fractionation of this plant extract led to the isolation of three active pentacyclic triterpenes, colubrinic acid (1), betulinic acid (2) and Alphitolic acid (3), as potent inhibitors. The inhibition of GLI-related protein expression with 1 or 2 was observed in HaCaT cells with exogenous GLI1, or human pancreatic cancer cells (PANC1), which express Hh/GLI components aberrantly. The expressions of GLI-related proteins PTCH and BCL2 were clearly inhibited by 1 or 2. We also examined the cytotoxicity of these active compounds against PANC1, human prostate cancer cells (DU145) and mouse embryo fibroblast cells (C3H10T1/2). The cytotoxicity against cancer cells (PANC1 and DU145) by 1 or 2 would be caused by inhibition of the expression of the anti-apoptosis protein BCL2. These pentacyclic triterpene inhibitors showed an important relationship between Hh/GLI signaling inhibition, the decrease of BCL2, and cytotoxicity against cancer cells.
