3BETA-HYDROXY-12-URSEN-28-OIC ACID
ursolic acid
CAS: 77-52-1
Molecular Formula: C30H48O3
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Names and Identifiers
| Name | ursolic acid |
| Synonyms | ursolic acid Ursoliic acid (3beta)-urs-12-en-28-oicaci 3B-HYDROXYURS-12-EN-28-OIC ACID 3BETA-HYDROXY-12-URSEN-28-IC ACID (3beta)-3-hydroxyurs-12-en-28-oate 3BETA-HYDROXY-12-URSEN-28-OIC ACID 3beta-Hydroxyurs-12-en-28-oic acid (3beta)-3-hydroxyurs-12-en-28-oic acid 3-hydroxy-,(3.beta.)-Urs-12-en-28-oicacid (3beta,5xi,18alpha)-3-hydroxyurs-12-en-28-oic acid Ursolic acid 3beta-Hydroxyurs-12-en-28-oic acid (1S,2R,4aS,6aS,6bR,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 |
| CAS | 77-52-1 |
| EINECS | 201-034-0 |
| InChI | InChI=1/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/p-1/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 |
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Physico-chemical Properties
| Molecular Formula | C30H48O3 |
| Molar Mass | 456.71 |
| Density | 1.0261 (rough estimate) |
| Melting Point | 292 °C (dec.) (lit.) |
| Boling Point | 502.79°C (rough estimate) |
| Specific Rotation(α) | 59 º (c=0.3, pyridine) |
| Flash Point | 304.6°C |
| Water Solubility | insoluble |
| Solubility | Soluble in methanol, acetone, pyridine, insoluble in water and petroleum ether. |
| Vapor Presure | 1.01E-14mmHg at 25°C |
| Appearance | glossy prismatic (anhydrous ethanol) or fine hair-like needle-like crystals (dilute ethanol) |
| Color | White to off-white |
| Merck | 14,9890 |
| BRN | 2228563 |
| pKa | 4.68±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months. |
| Refractive Index | 1.4940 (estimate) |
| MDL | MFCD00009621 |
| Physical and Chemical Properties | melting point 283-285°C |
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | - |
| RTECS | YU9520000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29181990 |
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Introduction
Open Data Unverified Data
ursolic acid, also known as ursolic acid and ursolic acid, is a kind of pentacyclic triterpenoid compound extracted from the bear fruit of Evergreen, in absolute ethanol, large, shiny prisms are obtained, while in dilute ethanol, wool-like needles are obtained. mp285 ℃ ~ 288 ℃,[α]D20 66 ° (pyridine), soluble in dioxane, pyridine, soluble in methanol, ethanol, butanol, butanone, slightly soluble in acetone, slightly soluble in benzene, chloroform, ether, insoluble in water and petroleum ether. With sedation, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, lower blood sugar and other biological effects. In recent years, it has been found that it has the effects of anti-carcinogenic, anti-promoting cancer, inducing F9 teratoma cell differentiation and anti-angiogenesis. It is very likely to become a new anti-cancer drug with low toxicity and high efficiency. In addition, ursolic acid has obvious antioxidant function and is a strong antioxidant. The antioxidant effect of ursolic acid has a positive effect on the anti-aging, skin freckle and pigment removal of human body, therefore, it is widely used as a raw material for medicine and natural whitening cosmetics. Experiments show that ursolic acid can inhibit the activity of 5-lipoxygenase and cyclooxygenase in the metabolism of arachidonic acid and prevent the formation of prostaglandins and leukotrienes, this may be the reason why ursolic acid inhibits inflammatory reaction and inhibits lipid peroxide.
Last Update：2022-01-01 08:50:12
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Physical properties
Open Data Unverified Data
high content of ursolic acid is glossy prismatic (absolute ethanol) or fine hair-like needle-like crystals (dilute ethanol), low content is Brown yellow or yellow green powder, with special odor, it is a pentacyclic triterpenoid found in natural plants. Melting point 283-288 ° C. Specific optical rotation [α]D25 +67.5 °(C = 1,1mol/L potassium hydroxide in alcoholic solution). At 15 ° C, ethanol (99%)1 mL can dissolve 10 mg, boiling 1 mL can dissolve 45 mg. Soluble in methanol, acetone, pyridine, insoluble in water and petroleum ether.
detection condition
- in order to better separate ursolic acid and oleanolic acid, the chromatographic column of a famous foreign company should be used, and the reason for the company in the production process is summarized.
- using Agilent C18 column, with acetonitrile: water (volume ratio 93:7) solution as mobile phase, with UV detector at 210Nm. Ethanol dissolved, standard dissolved 8-12mg/25m.
Production Process Flow
The crushed leaves of Eriobotrya japonica or ligustrum lucidum were extracted by ethanol reflux to obtain a liquid extract, and the ethanol was recovered. The above extracts were fully washed with water and dried to obtain a dry extract, dry extract is dissolved with ethanol and then decolorized. The decolorized solution is recovered by adding water to precipitate a large amount of precipitate after ethanol is recovered. The pH value is adjusted to 2-2.5, the main component of the crude extract was ursolic acid.
Last Update：2022-01-01 08:50:13
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Plant-determination of ursolic acid content
Open Data Unverified Data
chromatographic conditions
silica gel G thin layer plate; Cyclohexane-chloroform-ethyl acetate (20:5:8) as the developing solvent, ascending development; 12 ~ 18cm;5% sulfuric acid ethanol solution, 110 C heating 5min color.
preparation of reference solution
an appropriate amount of ursolic acid control was accurately weighed, and a mixed solution of absolute ethanol: ethanol (3:2) was added to prepare a solution containing 1mg per ml as a control solution.
sample solution preparation
20g of crushed sample of Gardenia jasminoides Ellis was precisely weighed (the sample was weighed according to the yield rate), then placed in a Soxhlet extractor, and refluxed with 300ml of diethyl ether until colorless. The solvent was recovered to dryness, the residue was soaked in petroleum ether for 2 times, 15ml each time, for about 2min. The residue was poured into petroleum ether, dissolved with anhydrous ethanol-diethyl ether (2:3) mixed solution heated slightly, and then placed in a 5ml measuring flask, as a sample solution.
assay
2 μl of the sample solution and the reference solution were accurately picked up and spotted on the same thin layer plate. Developed and developed according to the above chromatographic conditions. Scanning according to thin-layer scanning method, & lambda;S = 520nm,& lambda;R = 700nm; Double-wavelength reflectivity Sawtooth scanning; SX = 3.0; Slit: 1.20mm × 1.2; Paper speed: 20mm/min. The absorbance integral value of the sample and the reference substance was measured, and the content of ursolic acid was calculated.
Last Update：2022-01-01 08:50:15
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Pharmacological Efficacy
Open Data Unverified Data
- ursolic acid is a triterpenoid found in natural plants, with sedative, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, lower blood sugar and other biological effects, ursolic acid also has obvious antioxidant function, so it is widely used as a raw material for medicine and cosmetics.
- The clinical manifestations of ursolic acid have significant and rapid reduction of alanine aminotransferase, serum transaminase, yellow gangrene, increase appetite, anti-fibrosis and restore liver function, with quick effect, short course of treatment, the effect of stable characteristics.
- Indian scholar Saraswat et al found that ursolic acid (5~20 mg · kg) had a protective effect on liver toxicity induced by cc1. Pretreatment with ursolic acid can significantly improve the survival rate of rat liver cells, and the effect of ursolic acid on anti-cholestasis was observed in the experiment, and the bile flow and its contents were increased. From the mechanism of action of CC1, it is speculated that the therapeutic mechanism of ursolic acid on liver cells may be similar to its isomer oleanolic acid, which is to protect and stabilize the biofilm system of liver cell membrane and organelles, the change of permeability and active transport function returned to normal, the movement and distribution of ions and water inside and outside the cell were also restored, and the regeneration ability was recovered one after another, which promoted the repair of necrotic liver cells in the central area of liver lobules.
- "research and development of a new class of anti-hepatitis traditional Chinese medicine, ursolic acid and its preparations" has made great progress. It was included in the 863 National "1 million" program and received yuan of national scientific research funding, become a national major research topic (2002AA2Z3217).
- ursolic acid is a strong antioxidant. Experiments have shown that ursolic acid can inhibit arachidonic acid metabolism in the process of 5-lipoxygenase, epoxidase activity, prevent prostaglandin and leukotriene formation, this may be ursolic acid inhibit inflammatory reaction, causes of inhibition of lipid peroxides. Subbaramaiah et al. studies have shown that ursolic acid can inhibit the transcription of cyclooxygenase in human breast epithelial cells, thereby inhibiting prostaglandin production.
- ursolic acid has obvious stabilizing and cooling effects on the central nervous system.
Last Update：2022-01-01 08:50:17
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Clinical application
Open Data Unverified Data
Li Kaiquan et al. found that UA is used alone or in combination with other drugs in the preparation of drugs for the treatment of viral hepatitis, as long as the preparation of drugs or health care drugs have a significant effect on the treatment of viral hepatitis. They used oleanolic acid as a control, 102 cases of acute hepatitis A and B were treated with UA, the doses were 102 and 60 mg · d ~, the average treatment time was 21 days, 89.3% Recovery Rate, the curative effect was better than that of 100 cases of oleanolic acid control group (68% ,P< 0.01). Clinical trials have proved that UA has a significant and rapid reduction of alanine aminotransferase, jaundice, the role of recovery of liver function. After 3 weeks of treatment, the negative rate of 21 cases of HBeAg positive patients was 61.9%, and the negative rate of 21 cases of HBsAg positive patients was 42.8%, which indicated that it also had a certain therapeutic effect on hepatitis B. In addition, Tan Renxiang and other studies have also confirmed that UA not only has the effect of treating viral hepatitis, but also has an antidepressant effect, and the Perilla extract containing UA is used as a drug for treating depression. UA almost no adverse reactions, compared with Western medicine antidepressant spectrum narrow, toxic side effects, easy to relapse after treatment and induced Suicide tendency has a significant advantage. The capsule made of the extract of ligustrum lucidum leaves with UA as the main component is mainly used for primary hyperlipidemia caused by Yin deficiency of liver and kidney, Yin deficiency and hyperactivity of Yang. It is the second class of new drugs approved in China.
Last Update：2022-01-01 08:50:18
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Toxicological studies
Open Data Unverified Data
ursolic acid has a certain toxic effect on sperm, it can destroy the actin of the gallbladder Bridge, open the bridge, produce the co-plastid, inhibit the formation of sperm, the use of this role is expected to be developed into a male contraceptive.
Last Update：2022-01-01 08:50:18
3BETA-HYDROXY-12-URSEN-28-OIC ACID - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | ursolic acid is also known as ursolic acid, ursolic acid, it is a kind of pentacyclic triterpenoid compound extracted from the bear fruit of the evergreen racemic shrub of rhododendron family. It has a special smell, and has a large and glossy prism in anhydrous ethanol, in dilute ethanol, the fine needle crystals are as fine as hair. mp285 ℃ ~ 288 ℃,[α]D20 66 ° (pyridine), soluble in dioxane, pyridine, soluble in methanol, ethanol, butanol, butanone, slightly soluble in acetone, slightly soluble in benzene, chloroform, ether, insoluble in water and petroleum ether. With sedation, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, lower blood sugar and other biological effects. In recent years, it has been found that it has the effects of anti-carcinogenic, anti-promoting cancer, inducing F9 teratoma cell differentiation and anti-angiogenesis. It is very likely to become a new anti-cancer drug with low toxicity and high efficiency. In addition, ursolic acid has obvious antioxidant function and is a strong antioxidant. The antioxidant effect of ursolic acid has a positive effect on the anti-aging, skin freckle and pigment removal of human body, therefore, it is widely used as a raw material for medicine and natural whitening cosmetics. Experiments show that ursolic acid can inhibit the activity of 5-lipoxygenase and cyclooxygenase in the metabolism of arachidonic acid and prevent the formation of prostaglandins and leukotrienes, this may be the reason why ursolic acid inhibits inflammatory reaction and inhibits lipid peroxide. |
| plant sources | ursolic acid is widely distributed in the plant kingdom, such as hawthorn, Cornus officinalis, hedyotis diffusa, gardenia, psyllium, prunella vulgaris L. All contain ursolic acid, which is distributed in the form of free form or glycoside combined with sugar in about 7 families, 46 genera and 62 species of plants, mainly the leaves of ligustrum lucidum, rhododendron plants bear fruit, Rosaceae plants of the leaves, plants of paulownia tomentaceae leaves, Labiatae plant Prunella vulgaris whole grass, Ilex Ilex Ilex Ilex leaves and so on. |
| efficacy and function | ursolic acid is a triterpenoid compound present in natural plants, with sedative, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, lower blood sugar and other biological effects, ursolic acid also has obvious antioxidant function, in addition, ursolic acid can also induce cell apoptosis, inhibit cell cycle progression, inhibit cell proliferation, its anti-cancer activity is exhibited by inhibition of metastasis and reduction of tumorigenesis through various signaling pathways. experimental studies have shown that ursolic acid inhibits a variety of cancers, including bladder cancer, colon cancer, breast cancer, cervical cancer, gastric cancer, glioma, neuroblastoma, fibrosarcoma, liver cancer, leukemia, multiple myeloma, lung cancer, ovarian cancer, pancreatic cancer, thyroid cancer, melanoma and prostate cancer. In order to further understand and study the role of ursolic acid in cancer, opening a new chapter in chemotherapy, scientists have conducted a variety of in vivo and in vitro studies. |
| Anti-tumor effect | ursolic acid is also resistant to a variety of carcinogenic and carcinogenic substances, the study found that ursolic acid can significantly inhibit the proliferation of HL-60 cells and induce their apoptosis; Can significantly improve the phagocytosis of macrophages in mice, can inhibit the proliferation of human tongue squamous cell carcinoma cell line TSCCa cells, the half inhibitory dose on the growth of TSCCa cells was about 12.5Umol · L-1, which showed a dose-effect relationship within 24 hours; in situ hybridization showed that the inhibitory effect of ursolic acid on TSCCa cells was related to the inhibition of nuclear transcription factor expression in situ. In vivo experiments show that ursolic acid can significantly enhance the body's immune function. These results indicate that ursolic acid has extensive anti-tumor effects, and ursolic acid is likely to become a new anti-cancer drug with low toxicity and effectiveness. ursolic acid has preventive and inhibitory effects on various stages of tumor formation and growth, inhibits tumor formation and growth, and induces cancer cell differentiation. LiJ et al. have proved through experiments and clinical trials that ursolic acid can resist DNA mutation and inhibit the initiation of cancer, and ursolic acid can resist carcinogens such as benzopyrene and aflatoxin Bl-induced gene mutation. Wang Peng test on the early antibody (EBV-EA) activation test type to screen the inhibitor of skin cancer promoting substances, found that ursolic acid on TPA induced Raji cell EBV-EA activation has almost the same inhibitory effect as retinoic acid, and the survival rate of Raji cells was higher; The use of isotope labeled foester compound 3H-PDB2 proved that ursolic acid did not affect the binding of TPA and receptor, not by competing for TPA sites, but effectively block the carcinogen and receptor binding after the link to play a role. Studies by Guevara et al. have shown that ursolic acid can reduce the number of polychromatin micronucleated red blood cells by 76% induced by mutagens. Ohimachi and other research results show that ursolic acid on phorbol ester (TPA) induced Raji cell EBA-EA activation inhibition, its degree and retinoic acid is almost the same, Raji cell survival rate is higher than the retinoic acid treatment group, the mechanism is to effectively block the binding of TPA to the receptor. Hng et al found that ursolic acid can significantly inhibit TPA on dimethyl benzene and anthracene (DMBA) induced mouse skin cancer promoting effect, the mechanism is that TPA can induce epidermal ornithine decarboxylase (ODC) activity enhancement, ursolic acid can inhibit the above links, thereby causing polyamine depletion, growth inhibition, so that cells accumulate in the early, and differentiation. |
| determination of plant ursolic acid content | (1) chromatographic conditions: silica gel G thin layer plate; Cyclohexane-chloroform-ethyl acetate (20:5:8) for the development of the agent, the upward spread; The development of 12 ~ 18cm;5% sulfuric acid ethanol solution, 110 degrees C heating 5min color. (2) preparation of reference solution: accurately weigh an appropriate amount of ursolic acid reference, and add a mixed solution of anhydrous ethanol: ethanol (3:2) to make a solution containing 1mg per ml, as a control solution. (3) preparation of sample solution: precisely weigh 20g of the crushed sample of Gardenia jasminoides Ellis (weigh the sample after roasting the Gardenia fructus according to the yield), and place it in the Soxhlet extractor, add 300ml of ether and extract to colorless, recover the solvent to dryness, the residue is soaked in petroleum ether 2 times, 15ml each time, about 2min, pour off the petroleum ether, with anhydrous ethanol-ether (2:3) the mixed solution was dissolved by micro-heating and fixed in a 5ml measuring flask as a sample solution. (4) measurement: 2 μl of the sample solution and the reference solution were accurately absorbed and placed on the same thin layer plate. Developed and developed according to the above chromatographic conditions. Scanning according to the thin layer scanning method, λs = 520nm, λr = 700nm; Double wavelength reflection method Sawtooth scanning; SX = 3.0; Slit: 1.20mm × 1.2; Paper speed: 20mm/min. The absorbance integral value of the sample and the reference substance was measured, and the content of ursolic acid was calculated. |
| safety/side effects | Cosmetic Database, Cosmetic Ingredient Review Committee (CIR) or other regulatory agencies have not evaluated ursolic acid. However, it is generally considered a natural, safe ingredient, and no studies have found any side effects of its use. |
| Use | for content determination/identification/pharmacological experiments. A hydroxy pentacyclic triterpenoic acid (HPTA) with antibacterial, anticancer, antioxidant and anti-inflammatory effects. |
| production method | is present in Prunella vulgaris L. Ilex rotunda Thunb. The leaves of such many plants. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:54:55
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