(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid
oleanolic acid
CAS: 508-02-1
Molecular Formula: C30H48O3
(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid - Names and Identifiers
| Name | oleanolic acid |
| Synonyms | Oleanic acid oleanolic acid astrantiageninc Oleanolic acid Extract (3beta)-olean-12-en-28-oicaci (3-beta)-olean-12-en-28-oicaci 3-beta-hydroxy-olean-12-en-28-oicaci 3-beta-Hydroxyolean-12-en-28-oic Acid (3-beta)-3-hydroxyolean-12-en-28-oicacid (3beta)-3-hydroxyolean-12-en-28-oic acid Olean-12-en-28-oicacid, 3-hydroxy-, (3β)- (3beta,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid (3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid |
| CAS | 508-02-1 |
| EINECS | 208-081-6 |
| InChI | InChI=1/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20?,21?,22?,23-,27-,28+,29+,30-/m0/s1 |
| InChIKey | NZQIXFRGWXNLSP-IDYUENATSA-N |
(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid - Physico-chemical Properties
| Molecular Formula | C30H48O3 |
| Molar Mass | 456.7 |
| Density | 1.0261 (rough estimate) |
| Melting Point | >300 °C (lit.) |
| Boling Point | 502.79°C (rough estimate) |
| Specific Rotation(α) | D20 +83.3° (c = 0.6 in chloroform) |
| Flash Point | 302.6°C |
| Solubility | Soluble in methanol, ethanol, benzene, ether, acetone and chloroform, almost insoluble in water. |
| Vapor Presure | 1.47E-14mmHg at 25°C |
| Appearance | White needle crystal |
| Color | light yellow |
| Merck | 14,6827 |
| pKa | 2.52(at 25℃) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4940 (estimate) |
| MDL | MFCD00064914 |
| Physical and Chemical Properties | Melting point> 300°C |
| Use | Suitable for all types of hepatitis, with the promotion of liver cell regeneration, accelerate the repair of damaged liver cells, and strong heart, diuretic and anti-inflammatory effects |
(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection S60 - This material and its container must be disposed of as hazardous waste. S37 - Wear suitable gloves. |
| WGK Germany | 2 |
| RTECS | RK0177965 |
| TSCA | Yes |
| HS Code | 29181990 |
(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid - Nature
Open Data Verified Data
white crystalline powder. Melting point of 310 ° C, odorless, tasteless, optical rotation [83.3.. Practically insoluble in water, slightly soluble in ethanol and chloroform.
Last Update：2024-01-02 23:10:35
(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid - Preparation Method
Open Data Verified Data
- wood and wood root bark was cut into small pieces or filamentous by alcohol extraction, refluxed with 70% ml of ethanol for 3 times, about 3h each time, and the alcohol extracts were combined; Then most of the ethanol was recovered by distillation, add sulfuric acid to make the concentration of 15%, reflux for 2H, cool and filter, wash the filter cake with water for 3 times, then boil with 3% NaOH solution for 2 times, boil with water for 1 time, after each boiling filtration, can be gray-white crude sodium salt. Add about 8 times the amount of 85% ethanol, 0.5% activated carbon, reflux 40 min, filter, filtrate with HC1 to pH 3~4, overnight, filter, the filter cake was washed with distilled water to no chloride ion, and dried to obtain oleanolic acid fine product.
- after the block of wood and wood root bark was crushed by water extraction method, it was decocted with water for 3 times, about th each time, and the combined water decoction was concentrated into a dilute paste; Then concentrated sulfuric acid was added and stirred continuously, make its concentration to 20%, heat about th, cool and dilute with water, filter, filter cake after washing, with 3 %NaOH solution boiling 2 times, water boiling 1 times, after each boiling, the crude sodium salt was obtained by filtration. Add about 8 times the amount of more than 85% ethanol, 0.5% activated carbon, reflux 40 min, filter, and then adjust the filtrate to pH 3~4 with HC1, place overnight, filter, the filter cake is washed with distilled water to no chloride ion and dried to obtain this product.
Last Update：2022-01-01 11:15:08
(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid - Use
Open Data Verified Data
oleanolic acid is a broad-spectrum antibacterial drug, which is clinically used to treat bronchitis, Pneumonia, acute tonsillitis, periodontitis, bacillary dysentery, acute gastroenteritis and urinary tract infection. In addition, the clinical also for the treatment of acute hepatitis.
Last Update：2022-01-01 11:15:08
(3alpha,5xi,9xi,18xi)-3-hydroxyolean-12-en-28-oic acid - Reference Information
Open Data Unverified Data
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | has the effects of protecting liver and reducing enzymes, promoting liver cell regeneration, anti-inflammatory, cardiotonic, diuretic, anti-tumor, etc., and also has the effects of lowering blood sugar, lowering blood lipids, Sedative effect, is an effective ingredient in drugs such as treating liver disease and lowering blood sugar. It is clinically used to treat infectious acute icteric hepatitis. It has a significant effect of reducing glutamic pyruvic transaminase and reducing yellowing, improving the symptoms, signs and liver function of patients with viral and chronic persistent hepatitis; it can also be used for psoriasis, Rheumatoid arthritis, nephritis and edema, liver cirrhosis and ascites, acute and chronic hepatitis, stomach pain and turbidity, blood collapse, bruises, carbuncle swelling, waist and knee weakness, fetal movement and other symptoms. It is suitable for various types of hepatitis. It can promote the regeneration of liver cells, accelerate the repair of damaged liver cells, and has strong, diuretic and anti-inflammatory effects. liver disease adjuvant oleanolic acid is a natural triterpenoid compound, widely exists in food and medicinal plants. A triterpenoid compound isolated from medicinal plants. Anti-tumor and hepatoprotective agents. It was used as a reference compound in quantification by high-performance thin-layer chromatography (HPTLC) in the roots of the genus Stannia. |
| Ligustrum lucidum extract | Oleanolic acid is a pentacyclic triterpenoid compound isolated and extracted from the fruit of the Gentianaceae plant Swertia or Ligustrum lucidum. It exists in a variety of plants as free bodies and glycobodies. It has become a commonly used liver-protecting drug in clinical practice. It has a significant protective effect on acute and chronic liver damage in rats caused by carbon tetrachloride, it can reduce the elevated ALT and AST, reduce inflammation, necrosis and interstitial inflammation, prevent the formation of fibrosis, promote the regeneration of liver cells, and accelerate the recovery of necrotic tissue. Electron microscopy showed that the enlarged mitochondria and rough endoplasmic reticulum recovered after treatment with oleanolic acid. Its succinate can reduce the activity of cytochrome P450 enzyme in mouse liver microsomes. In addition, oleanolic acid has the effects of correcting protein metabolism disorders, reducing inflammation, strengthening the heart, diuresis, increasing white blood cells, lowering blood sugar, promoting immune function, and inhibiting the growth of S-180 tumor strains. The following figure shows the technological process of extracting oleanolic acid and ursolic acid from the dried and mature fruits of Ligustrum lucidum from the Oleaceae plant: the technological flow chart of extracting oleanolic acid from the mature fruits of Ligustrum lucidum [note 1] 95% ethanol reflux extraction 4 times, combine the extracts, and concentrate under reduced pressure. [Note 2] After dilute alcohol is dissolved, petroleum ether, ethyl acetate and n-butanol are respectively extracted. [note 3] low pressure silica gel column chromatography, petroleum ether-ethyl acetate gradient elution. |
| The effect of oleanolic acid | 1. Oleanolic acid has anti-inflammatory, sedative, cardiotonic, diuresis, lowering blood lipids, lowering blood sugar, protecting liver and reducing enzymes, enhancing immunity and inhibiting the growth of S180 tumor strains. It is an effective ingredient in the development of drugs for the treatment of liver disease and lowering blood sugar. 2. Oleanolic acid has protective effect on chromosome damage and preventive effect on experimental atherosclerosis. It is clinically used to treat infectious acute icteric hepatitis and chronic viral hepatitis. It has obvious effects of reducing glutamic-pyruvic transaminase and reducing yellow. 3. oleanolic acid has the effect of inhibiting liver fibrosis. in rats with liver fibrosis treated with oleanolic acid, liver fibrosis has severe and significantly reduced liver fibrosis, and liver collagen content is reduced, suggesting that it has the effect of preventing and treating liver cirrhosis. 4, reduce the brain homogenate of cirrhotic rats cool acid level: because the brain homogenate cool acid level decreased significantly, can inhibit the production of pseudo neurotransmitter, so it is conducive to the prevention and treatment of hepatic encephalopathy. 5. Oleanolic acid capsules are non-prescription drugs for liver disease, which are used for the adjuvant treatment of acute and chronic hepatitis. It has a certain protective effect on liver injury, which can reduce the elevated serum alanine aminotransferase, promote the regeneration of liver cells, and accelerate the repair of necrotic tissue. |
| Olean fruit | Olean fruit, also known as "olive", is a very typical woody oil plant in the Mediterranean region. Belongs to Oleaceae. The ancient Greeks and Jews took the fruit of the year as a sign of peace. In western spotted teeth, Italy and Argentina, oleuncularine occupies a huge area. It is less distributed elsewhere. Olean fruit is a tree with a height of 3-7 meters. Its leaves are evergreen and drupe are as long as 1-3cm. Its mesocarp contains 25-40% olean oil, rich in vitamins and is easy to be digested by organisms. In medicine, this oil is used to prevent arteriosclerosis. At present, it mainly grows in cultivated or wild state. There are about 60 species in Olea, such as olea chrysophylla, O.europaea and oleaeuropaea var. communis. Olean fruit plant map |
| clinical application | oleanolic acid is an anti-hepatitis drug. clinically, it is mainly used to treat acute icteric hepatitis with remarkable curative effect and good effect on chronic hepatitis. The symptoms, signs and liver function were significantly improved. In addition, there is the role of correcting protein metabolism disorders. |
Last Update：2024-04-09 19:43:38
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