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Ursolic acid

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Ursolic acid Basic information
Overview Plant sources Antitumor Effect Determination of ursolic acid content of plant
Product Name:Ursolic acid
Synonyms:(3beta)-urs-12-en-28-oicaci;3-hydroxy-,(3.beta.)-Urs-12-en-28-oicacid;3BETA-HYDROXY-12-URSEN-28-IC ACID;3BETA-HYDROXY-12-URSEN-28-OIC ACID;3B-HYDROXYURS-12-EN-28-OIC ACID;3beta-hydroxyurs-12-en-28-oic acid;(1S,2R,4AS,6AS,6BR,8AR,10S,12AR,12BR,14BS)-10-HYDROXY-1,2,6A,6B,9,9,12A-HEPTAMETHYL-1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B-ICOSAHYDROPICENE-4A-CARBOXYLIC ACID;MALOL
CAS:77-52-1
MF:C30H48O3
MW:456.7
EINECS:201-034-0
Product Categories:Pentacyclic Triterpenes;Tri-Terpenoids;Organics;chiral;Natural Plant Extract;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Antineoplastic;natural product;Plant extract;Inhibitors;Triterpenoids
Mol File:77-52-1.mol
Ursolic acid Structure
Ursolic acid Chemical Properties
mp 292 °C (dec.)(lit.)
alpha 59 º (c=0.3, pyridine)
storage temp. 2-8°C
Water Solubility insoluble
Merck 9890
CAS DataBase Reference77-52-1(CAS DataBase Reference)
EPA Substance Registry SystemUrs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-(77-52-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36-26
WGK Germany -
10-23
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
Ursolic acid Usage And Synthesis
OverviewUrsolic acid is a kind of pentacyclic triterpenoids extracted from azaleas evergreen shrubs bearberry. It has a special smell. It exhibits big and shiny prism in absolute ethanol, and exhibits fine hair-like needle crystal in dilute ethanol. Its m.p is 285 °C ~ 288 °C, [α] D20 + 66 ° (pyridine). It is highly soluble in dioxane, pyridine, soluble in methanol, ethanol, butanol, and methyl ethyl ketone, slightly soluble in acetone, slightly soluble in benzene chloroform, and ethyl ether, but insoluble in water and petroleum ether. It has various kinds of biological effects including sedation, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, and lowering blood sugar. In recent years, we found that it has the ability of anti-carcinogenic, anti-tumor promoters, inducing F9 teratoma cells differentiation and anti-angiogenesis, making it likely to become a promising novel anti-cancer drug of low toxicity and high efficiency. In addition, ursolic acid has significant antioxidant function and is a strong antioxidant. The anti-oxidation effect of ursolic acid has a positive effect on the body's anti-aging, alleviating skin spot, and pigment elimination, which is thus widely used as the raw materials of medicine and natural whitening cosmetics. There has been experiment showing that ursolic acid can inhibit the activity of 5-lipoxygenase and cyclooxygenase during the metabolism of arachidonic acid to prevent the biosynthesis of prostaglandins and leukotrienes, which may be mechanism through which ursolic acid can inhibit inflammation reaction and inhibit lipid peroxides reasons.
Plant sourcesUrsolic acid is widely distributed in the plant kingdom. A various kinds of plants including traditional Chinese medicine hawthorn, dogwood, diffusa, gardenia, Plantago asiatica, Prunella vulgaris all contain ursolic acid. As either a free form or be in the form glycosides through binding with sugar, it is distributed among about 62 kinds of plants from 7 families and 46 genera. It is mainly presented in the leaves of Oleaceae plant privet, Ericaceae bearberry, leaves of Rosaceae loquat, leaves of Scrophulariaceae paulownia tomentosa, the full grass of Labiatae Prunella, and also the leaves of Aquifoliaceae llex rotunda.
Antitumor EffectUrsolic acid can also fight against various kinds of carcinogens and tumor promoters. Studies have found that ursolic acid can significantly inhibit the proliferation of HL-60 cell and induce its apoptosis; can significantly improve the function of the mouse macrophage; can inhibit the proliferation of human tongue squamous carcinoma cell line TSCCa cell with the LD50 being 12.5Umol • L-1 as well as exhibiting a dose-dependent efficacy relationship within 24h; situ hybridizations assay showed that the inhibitory effect of ursolic acid on TSCCa cells in vitro is related to the in situ inhibition of the expression of nuclear transcription factor. In Vivo tests have demonstrated that ursolic acid can significantly enhance immune function, clarifying the broad anti-tumor effect of ursolic acid. From this perspective, ursolic acid is very likely to become a new anti-cancer drug with low toxicity and high efficiency.
Determination of ursolic acid content of plant(1) Chromatographic conditions: silica gel G plate; cyclohexane - chloroform - ethyl acetate (20: 5: 8) as the developer agent, apply ascending development with development gap being from 12 ~ 18cm; 5% sulfuric acid in ethanol; apply 110 °C heating for 5min for colorimetric reaction.
(2) The preparation of the reference solution: Accurately weigh a certain amount of ursolic acid reference substance; add the mixed solution of absolute ethanol: ethanol (32) to prepare to solution of 1 mg/mL as the reference solution.
(3) Preparation of the sample solution: Accurately weigh gardenia pulverized sample 20g (for fried gardenia, calculate after being normalized with the yield) and put it into the Soxhlet extractor, add 300 mL ether for reflux extraction to being colorless; recycle solvent to dryness with the residue being added petroleum ether for soaking for 2 times (15ml each time), soak for about 2min, pour out the petroleum ether, apply anhydrous ethanol - ethyl ether (2: 3) mixture for micro heating to dissolve it and make constant volume solution in 5ml flask as the sample solution.
(4) Determination: accurately pipette 2 μl of sample solution and reference solution 2 into the same TLC plate. Develop them according to the chromatographic conditions and start colorimetric reaction. Scan it according to TLC scanning method, λS = 520nm, λR = 700nm; apply dual wavelength reflection zigzag scanning; SX = 3.0; slit: 1.20mm × 1.2mm; paper speed: 20mm / min. Measure the integral value of absorption of both the sample and the reference substance for calculating the absolute amount of ursolic acid.
The above information is edited by the chemicalbook of Dai Xiongfeng.
Chemical Propertieswhite to light yellow crystal powde
UsageA Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties.
Ursolic acid Preparation Products And Raw materials
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