(3beta)-stigmast-5-en-3-ol
beta-Sitosterol
CAS: 83-46-5
Molecular Formula: C29H50O
(3beta)-stigmast-5-en-3-ol - Names and Identifiers
| Name | beta-Sitosterol |
| Synonyms | CINCHOL Sitosterol Phytosterol B-SITOSTEROL A-PHYTOSTEROL beta-Sitosterol 5-STIGMASTEN-3BETA-OL (3)-BETA-SITOSTEROL(2) stigmast-5-en-3-beta-ol 24BETA-ETHYLCHOLESTEROL 22,23-DIHYDROSTIMASTEROL 24-ALPHA-ETHYLCHOLESTEROL beta-Sitosterol (1.03739) 22,23-DIHYDROSTIGMASTEROL (3beta)-stigmast-5-en-3-ol beta-sitosterol from soybean 5-CHOLESTEN-24-BETA-ETHYL-3-BETA-OL (3beta,8alpha,9beta,10alpha,24S)-stigmast-5-en-3-ol (3S,10R,13R,17R)-17-(4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| CAS | 83-46-5 |
| EINECS | 201-480-6 |
| InChI | InChI=1/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20?,21?,23-,24?,25+,26?,27?,28-,29+/m0/s1 |
| InChIKey | KZJWDPNRJALLNS-VJSFXXLFSA-N |
(3beta)-stigmast-5-en-3-ol - Physico-chemical Properties
| Molecular Formula | C29H50O |
| Molar Mass | 414.72 |
| Density | 0.9540 (rough estimate) |
| Melting Point | 136-140°C(lit.) |
| Boling Point | 473.52°C (rough estimate) |
| Specific Rotation(α) | -28 º (c=2, CHCl3) |
| Flash Point | 220.4°C |
| Water Solubility | INSOLUBLE |
| Solubility | Insoluble in water, soluble in chloroform, benzene, ethanol, carbon disulfide and ether. |
| Vapor Presure | 3.53E-12mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| Merck | 14,8556 |
| BRN | 1916165 |
| pKa | 15.03±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5000 (estimate) |
| MDL | MFCD00003631 |
| Physical and Chemical Properties | Melting point 139-142°C specific optical rotation -28 ° (c = 2, CHCl3) water-soluble INSOLUBLE |
| Use | Used as hypolipidemic drug |
(3beta)-stigmast-5-en-3-ol - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R38 - Irritating to the skin R40 - Limited evidence of a carcinogenic effect R48/20/22 - R36/37/38 - Irritating to eyes, respiratory system and skin. R67 - Vapors may cause drowsiness and dizziness R36/38 - Irritating to eyes and skin. R20 - Harmful by inhalation R63 - Possible risk of harm to the unborn child |
| Safety Description | S22 - Do not breathe dust. 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. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 1888 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | WJ2600000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29061990 |
(3beta)-stigmast-5-en-3-ol - Nature
Open Data Verified Data
- the product line is a mixture of p-sitosterol and some saturated sterols (sterols), white, scaly, needle-like crystals or crystalline powder; Odorless and tasteless. It is very soluble in chloroform and carbon disulfide, slightly soluble in ethanol or acetone, and insoluble in water. The melting point was 13 6-140 °c.
- p-sitosterol is a steroid substance in vegetable oil, which can reduce the amount of plasma low density lipoprotein (LDL) and cholesterol in patients with Hyperlipoproteinemia, mainly by inhibiting the absorption of cholesterol. Because the chemical structure of this kind of drug is very similar to cholesterol, it can be used as a competitive inhibition of intestinal lumen cholesterol hydrolysis, and inhibit the re esterification of free cholesterol in intestinal mucosal epithelial cells. In addition, it can competitively occupy the position of cholesterol in the micelles, reducing the chance of contact between cholesterol and intestinal mucosal cells, thus preventing absorption.
Last Update：2024-01-02 23:10:35
(3beta)-stigmast-5-en-3-ol - Preparation Method
Open Data Verified Data
prepared by extraction of rice bran oil under the foot.
Last Update：2022-01-01 11:13:58
(3beta)-stigmast-5-en-3-ol - Use
Open Data Verified Data
- has the effects of lowering cholesterol, relieving cough, eliminating phlegm, inhibiting tumor and repairing tissue. For hypercholesterolemia, atherosclerosis and chronic bronchitis, also for early cervical cancer and skin ulcers.
- The ointment is mixed with glycerin, octanol, glyceryl monostearate and ethyl p-hydroxybenzoate, heated and melted, added with sitosterol, stirred to dissolve, and heated to 80~90 ℃ with appropriate amount of water, added with tween-80, stir well; Mix the two solutions well and cool.
- suppository mix sitosterol and polyglycol, heat and melt, slowly add 80~90 ℃ tween-80 solution while stirring, continue to stir evenly, and then let cool to 40 ℃, it is quickly injected into the bolt mold coated with lubricant, cooled and then taken out.
Last Update：2022-01-01 11:13:58
(3beta)-stigmast-5-en-3-ol - Safety
Open Data Verified Data
- may appear loss of appetite, Diarrhea, gastrointestinal pain and other gastrointestinal reactions.
- Storage and closed storage.
Last Update：2022-01-01 11:13:59
(3beta)-stigmast-5-en-3-ol - Reference Information
| Plant Source: | soybean |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Background | sterol (sterol) is a kind of steroid existing in nature, but it has high application value. Because of its solid state, also known as sterol, it belongs to macromolecular alcohols. It is the main component of unsaponifiable matter in oils and fats. According to different sources, sterols can be divided into three categories, namely animal sterols, plant sterols and bacterial sterols. |
| physiological function | phytosterol (sitosterol) is considered as a mild free radical scavenger, to some extent, this explains the active role of phytosterols in maintaining cell membrane stability, inhibiting inflammation, preventing and treating atherosclerosis and anticancer. Anti-inflammatory and immunomodulatory effects phytosterols have the effects of anti-inflammatory, anti-infection and inhibition of bacterial and fungal reproduction, and their anti-inflammatory effects are also one of the functions discovered earlier. |
| Main properties | The amphoteric character of phytosterols makes them have the ability to block and control the fluidity of reversed-phase membranes, phytosterol is mainly hydrophobic, but because of its structure with hydroxyl group, and thus has a certain hydrophilicity, the greater the side chain, the stronger the hydrophobicity of sterol, phytosterol specific gravity slightly greater than water, insoluble in water, soluble in a variety of organic solvents. |
| Application | phytosterols have extensive biological functions in medicine and food science. In animal production, the scientific use of phytosterols can promote animal growth, improve body health and improve the quality of animal products, which has a positive effect on reducing breeding costs and improving economic benefits. As a kind of functional additive, phytosterol has broad application prospects in feed industry. At present, the mechanism of action, effective dosage form and dosage, absorption efficiency and application technology of phytosterols to improve animal growth and health have not been fully clarified, and a lot of and in-depth research is needed, to lay the foundation for its scientific and rational application. |
| uses | β-sitosterol and β-sitosterol derivatives are widely used in medicine, food, cosmetics, feed and other industries. It has the effects of lowering cholesterol, relieving cough, eliminating phlegm, inhibiting tumor and repairing tissue. For type II hyperlipidemia, atherosclerosis and chronic bronchitis, also for early cervical cancer and skin ulcers. Large doses can appear loss of appetite, Diarrhea, gastrointestinal pain and other gastrointestinal reactions. Osteomyelitis caused by ulcers, in the original disease is not used before healing. Leg Ulcers with varicose veins of the lower extremities must be treated simultaneously. β-sitosterol has the effects of lowering cholesterol, relieving cough, eliminating phlegm, inhibiting tumor and repairing tissue. It can be used as hypolipidemic drugs for type II hyperlipidemia, atherosclerosis and chronic bronchitis, also for early cervical cancer and skin ulcers. Medical raw materials and health food. Beta-sitosterol, used to supplement the diet of mice, was found to have a significant effect on body mass accumulation. A phytosterol whose structure is very similar to cholesterol, has estrogenic activity. It inhibits proliferation (G2/M arrest), nuclear replication, and polymerization of α-tubulin and microtubules in human leukemia cells. used as hypolipidemic agent |
| properties | β-sitosterol is White scale-like, needle-like crystal or crystalline powder, odorless and tasteless. Mp136-140. It is very soluble in chloroform and carbon disulfide, slightly soluble in ethanol or acetone, and insoluble in water. |
| side effects | gastrointestinal reactions such as loss of appetite, Diarrhea, gastrointestinal pain may occur at large doses. Osteomyelitis caused by ulcers, in the original disease is not used before healing. Leg Ulcers with varicose veins of the lower extremities must be treated simultaneously. |
| consumption | ≤ 2.4g/day |
| applicable food category | scope of use does not include infant food |
| approval date | 2010-03-09 |
| Announcement No. | No. 3 of 2010 |
| announcement title | on the approval of DHA algal oil, cotton Seed oligosaccharides and other 7 kinds of articles for the new resources of food and other relevant provisions of the announcement |
| Trait | white powder or granule |
| Phytosterols | ≥90% |
| Β-sitosterol | ≥30.0% |
| Campesterol | ≥15.0% |
| Stigmasterol | ≥12.0% |
| production method | with rice bran oil as raw material, the alkali soap residue is dried in an oven at a constant temperature below 80 ℃ to make the water content less than 2%, dry soap residue, small particles or powder. Methane soap residue [below 80 ℃] → dry soap residue extraction dry soap residue is added into the enamel reaction tank, and acetone (V soap residue: V acetone = 1:8) is added and stirred, the jacket distillation steam is heated, refluxed and extracted at 50-55 °c for 3-4H, cooled to 30 °c for discharge, and left to stand at 10-15 °c for 12H. The filtrate is obtained by pressure filtration. Dry soap residue [acetone] →[50-55 ℃, 3-4h] filtrate concentration, crystallization, drying the filtrate into the concentration tank, concentrated to the original volume of 1/5, to obtain concentrated liquid, the crystals were allowed to stand at room temperature for 12h and filtered to obtain a crude product, which was dried in an oven at 60 ° C. To obtain a crude product. Filtrate [concentrated] → concentrated solution [crystallized] → crude product [60 ℃]→ decolorizing and crystallizing the dried crude product. Dry the dried crude product, add 25-30 times of 95% ethanol, add hydrochloric acid for pH3-4, and heat it in water bath, after dissolving the crude product, add 10-20g/L activated carbon to micro-boil for 20min, filter while hot to obtain filtrate, and let it stand at room temperature for 12h to crystallize, the product was obtained by vacuum drying below 80 ℃. Dry crude product [decolorization] → filtrate [crystallization] → crystalline product [below 80 ℃] → finished sitosterol product. |
Last Update：2024-04-09 21:21:28
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