Lupeolic acidCAS# 87355-32-6 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 87355-32-6 | SDF | Download SDF |
| PubChem ID | 12111950 | Appearance | Powder |
| Formula | C30H48O3 | M.Wt | 456.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1R,3aR,5aR,5bR,7aR,8R,9R,11aR,11bR,13aR,13bR)-9-hydroxy-3a,5a,5b,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-8-carboxylic acid | ||
| SMILES | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C(=O)O)O)C)C | ||
| Standard InChIKey | NYJYXELDYSTZFI-XSDHLHMPSA-N | ||
| Standard InChI | InChI=1S/C30H48O3/c1-18(2)19-10-13-26(3)16-17-28(5)20(24(19)26)8-9-21-27(4)14-12-23(31)30(7,25(32)33)22(27)11-15-29(21,28)6/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21+,22+,23+,24+,26+,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. Lupeolic acid has anti-inflammatory activity. |
| Targets | COX | PGE |
Lupeolic acid Dilution Calculator
Lupeolic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1896 mL | 10.9481 mL | 21.8962 mL | 43.7924 mL | 54.7405 mL |
| 5 mM | 0.4379 mL | 2.1896 mL | 4.3792 mL | 8.7585 mL | 10.9481 mL |
| 10 mM | 0.219 mL | 1.0948 mL | 2.1896 mL | 4.3792 mL | 5.4741 mL |
| 50 mM | 0.0438 mL | 0.219 mL | 0.4379 mL | 0.8758 mL | 1.0948 mL |
| 100 mM | 0.0219 mL | 0.1095 mL | 0.219 mL | 0.4379 mL | 0.5474 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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Analysis of pentacyclic triterpenic acids from frankincense gum resins and related phytopharmaceuticals by high-performance liquid chromatography. Identification of lupeolic acid, a novel pentacyclic triterpene.[Pubmed:12798161]
J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):21-30.
An HPLC gradient method with photodiode array detection was developed for the simultaneous analysis of 12 different pentacyclic triterpenic acids in Indian and African frankincense gum resins as well as in related phytopharmaceuticals. The triterpenic acids were obtained by an exhaustive extraction procedure. Identification of the compounds was based on retention times, UV-spectra and add on technique with standards isolated from African frankincense. The method allows differentiation of frankincense of different origin and standardization of frankincense-based phytopharmaceuticals. Further, this is the first report identifying a novel pentacyclic triterpene, Lupeolic acid, as a constituent of frankincense gum resins.
Tetra- and pentacyclic triterpene acids from the ancient anti-inflammatory remedy frankincense as inhibitors of microsomal prostaglandin E(2) synthase-1.[Pubmed:24844534]
J Nat Prod. 2014 Jun 27;77(6):1445-51.
The microsomal prostaglandin E2 synthase (mPGES)-1 is the terminal enzyme in the biosynthesis of prostaglandin (PG)E2 from cyclooxygenase (COX)-derived PGH2. We previously found that mPGES-1 is inhibited by boswellic acids (IC50 = 3-30 muM), which are bioactive triterpene acids present in the anti-inflammatory remedy frankincense. Here we show that besides boswellic acids, additional known triterpene acids (i.e., tircuallic, lupeolic, and roburic acids) isolated from frankincense suppress mPGES-1 with increased potencies. In particular, 3alpha-acetoxy-8,24-dienetirucallic acid (6) and 3alpha-acetoxy-7,24-dienetirucallic acid (10) inhibited mPGES-1 activity in a cell-free assay with IC50 = 0.4 muM, each. Structure-activity relationship studies and docking simulations revealed concrete structure-related interactions with mPGES-1 and its cosubstrate glutathione. COX-1 and -2 were hardly affected by the triterpene acids (IC50 > 10 muM). Given the crucial role of mPGES-1 in inflammation and the abundance of highly active triterpene acids in frankincence extracts, our findings provide further evidence of the anti-inflammatory potential of frankincense preparations and reveal novel, potent bioactivities of tirucallic acids, roburic acids, and Lupeolic acids.
