Anti-stiffness factor
Stigmasterol
CAS: 83-48-7
Molecular Formula: C29H48O
Anti-stiffness factor - Names and Identifiers
| Name | Stigmasterol |
| Synonyms | Stigmasterol Anti-stiffness factor Stigmasta-5,22-dien-3beta-ol stigmasta-5,22-dien-3-beta-ol 22-Dehydro-24-ethylcholesterol (22Z)-stigmasta-5,22-dien-3-ol (5beta,22E)-stigmast-22-en-3-one (3β,22E)-StigMasta-5,22-dien-3-ol 24-Ethylcholesta-5,22-dien-3beta-ol (3beta,22E)-stigmasta-5,22-dien-3-ol (22E,24S)-Stigmasta-5,22-diene-3β-ol (24S)-24-Ethylcholesta-5,22-dien-3β-ol (22E,24S)-24-Ethylcholesta-5,22-dien-3β-ol Stigmasterol,3β-Hydroxy-24-ethyl-5,22-cholestadiene, 5,22-Stigmastadien-3β-ol, Stigmasterin |
| CAS | 83-48-7 |
| EINECS | 201-482-7 |
| InChI | InChI=1/C29H48O/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/h8-9,19-22,24-27H,7,10-18H2,1-6H3/b9-8+/t20-,21-,22-,24+,25-,26+,27+,28+,29-/m1/s1 |
Anti-stiffness factor - Physico-chemical Properties
| Molecular Formula | C29H48O |
| Molar Mass | 412.7 |
| Density | 0.9639 (rough estimate) |
| Melting Point | 165-167 °C (lit.) |
| Boling Point | 472.07°C (rough estimate) |
| Specific Rotation(α) | -50 º (c=2, CHCl3) |
| Flash Point | 204.1°C |
| Water Solubility | insoluble |
| Solubility | Soluble in chloroform, benzene, ethyl acetate, pyridine, soluble in ethanol, acetone. Insoluble in water. |
| Vapor Presure | 9.21E-10mmHg at 25°C |
| Appearance | White solid |
| Color | White |
| Maximum wavelength(λmax) | ['226nm(MeOH)(lit.)'] |
| Merck | 14,8815 |
| BRN | 2568182 |
| pKa | 15.03±0.70(Predicted) |
| Storage Condition | -20°C |
| Refractive Index | 1.5000 (estimate) |
| MDL | MFCD00003630 |
| Physical and Chemical Properties | Melting point 165-167°C(lit.) specific rotation -50 ° (c = 2, CHCl3) storage conditions 0-6°C water-soluble insoluble Merck 8814 |
| Use | Used as a raw material for the synthesis of steroid hormones, can also be used as a raw material for the production of vitamin D3 |
Anti-stiffness factor - 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. S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 1888 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | WJ2447500 |
| HS Code | 29309070 |
Anti-stiffness factor - Reference
| Reference Show more | 1. Jiang Zhao-Jing, Liu Zhong, Boma Hanjun, etc. Law of curing sunflower seed oil with mixture of monoglyceride and stigmasterol [J]. Food science 2020(15):22-30. 2. Ji Man, Sun Peidong. Analysis of active lipids in longan nucleus and their cell proliferation activity [J]. China Oil & Fat, 2019(8). 3. Li Gang, Xu Shuya, Zhao Limin, et al. Correlation analysis of pollen typhae quality characterization based on drug system quality evaluation model [J]. Journal of Beijing University of Chinese Medicine, 2015, 23 (6):393-399. 4. Fu tiokun, Zhou Wei, Xia Wen, etc. Study on extraction technology of three main sterols from pitaya stem [J]. Journal of Tropical Agriculture Sciences, 2019, v.39;No.268(12):46-54. 5. Chen Ke, Wang Chang-Qian, Fan Yu-Qi, et al. Study on the lipid-lowering effect of seven traditional Chinese medicine monomers on zebrafish platform [J]. Journal of Physiology, 2017, 069(001):55-60. 6. Liu, Wei-Liang, et al. "Moringa oleifera Lam seed oil augments pentobarbital-induced sleeping behaviors in mice via GABAergic systems." Journal of agricultural and food chemistry 68.10 (2020): 3149-3162.https://doi.org/10.1021/acs.jafc.0c00037 7. [IF=5.64] Wu Dousheng et al."Oleanolic Acid Induces the Type III Secretion System of Ralstonia solanacearum."Front Microbiol. 2015 Dec;0:1466 8. [IF=5.279] Shanshan Wang et al."Enhancement of Galloylation Efficacy of Stigmasterol and β-Sitosterol Followed by Evaluation of Cholesterol-Reducing Activity."J Agr Food Chem. 2019;67(11):3179-3187 9. [IF=7.514] Qin Guo et al."Action of phytosterols on thermally induced trans fatty acids in peanut oil."Food Chem. 2021 May;344:128637 10. [IF=5.923] Lixiu Hou et al."Genome-Wide Identification of CYP72A Gene Family and Expression Patterns Related to Jasmonic Acid Treatment and Steroidal Saponin Accumulation in Dioscorea zingiberensis."Int J Mol Sci. 2021 Jan;22(20):10953 11. [IF=5.279] Shanshan Wang et al."Enhancement of Antioxidant Activity in O/W Emulsion and Cholesterol-Reducing Capacity of Epigallocatechin by Derivatization with Representative Phytosterols."J Agr Food Chem. 2019;67(45):12461-12471 12. [IF=4.511] Shuxian Zhao et al."Enhancing Effects of Theanine Liposomes as Chemotherapeutic Agents for Tumor Therapy."Acs Biomater Sci Eng. 2019;5(7):3373-3379 13. [IF=4.192] Wei-Liang Liu et al."Moringa oleifera Lam Seed Oil Augments Pentobarbital-Induced Sleeping Behaviors in Mice via GABAergic Systems."J Agr Food Chem. 2020;68(10):3149-3162 14. [IF=4.032] Qiu-yue Xiao et al."A network pharmacology-based study on key pharmacological pathways and targets of Qi Fu Yin acting on Alzheimer's disease."Exp Gerontol. 2021 Jul;149:111336 15. [IF=3.69] Yuyun Li et al."Prediction of the mechanisms of Xiaoai Jiedu Recipe in the treatment of breast cancer: A comprehensive approach study with experimental validation."J Ethnopharmacol. 2020 Apr;252:112603 16. [IF=4.766] Meng Qin et al.Misdiagnosis of sitosterolemia in a patient as Evans syndrome and familial hypercholesterolemia.J Clin Lipidol. 2021 Nov;: 17. [IF=3.645] Shuo Gu et al."Develop a stepwise integrated method to screen biomarkers of Baihe-Dihuang Tang on the treatment of depression in rats applying with composition screened, untargeted, and targeted metabolomics analysis."Journal Of Separation Science. 2022 M 18. [IF=7.514] Simin Feng et al."Simultaneous analysis of free phytosterols and phytosterol glycosides in rice bran by SPE/GC-MS."Food Chem. 2022 Sep;387:132742 19. [IF=4.556] Junpeng Zeng et al."The comparative analysis of different oil extraction methods based on the quality of flaxseed oil."J Food Compos Anal. 2021 Dec;:104373 |
Anti-stiffness factor - 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) |
| Introduction | stigmasterol is a natural phytosterol. Natural Phytosterols are similar in structure to animal sterols such as cholesterol. They are an active ingredient in plants and exist in various vegetable oils. They are widely used in medicine, food, cosmetics and other industries. |
| phytosterol | stigmasterol is a phytosterol, one of the major sterols in soybean oil. Stigmasterol is also found in Tetrandrine, cortex phellodendri, poisonous lentils and potatoes, as well as in marine phytoplankton, seawater and marine sediments. |
| method for extracting stigmasterol from plants | at present, the methods for extracting stigmasterol from mixed phytosterols at home and abroad mainly include: solvent method and solvent crystallization method. The solubility difference of each component in the mixed phytosterol was directly used to select the appropriate organic solvent for multi-step extraction and recrystallization separation; the organic acid and the alcohol hydroxyl group contained in the mixed phytosterol are esterified to generate the corresponding phytosterol derivative, which increases the difference of physical properties, and then the separation is carried out by recrystallization and other methods; the halogen addition reaction takes place by using the double bond on the sterol ring and the branched chain, so that the difference of the physical parameters of the generated derivative becomes large, and then the appropriate organic solvent is selected for extraction and recrystallization separation. 1, solvent method, using soybean mixed plant Street alcohol as raw material, by adjusting the solid-liquid ratio and crystallization temperature, it is proved that after 2-3 step crystallization, A purity of> 60% betherol can be obtained. Through 5 A 4 grade crystallization, the purity can reach more than 85%. 2. Solvent crystallization The Process comparison of separating mixed phytosterols from solvent crystallization shows that the presence of a small amount of water can not only greatly improve the yield of sterols, stigmasterol selectivity can also be improved in certain ranges, which helps to obtain high purity stigmasterol and sitosterol products. 2.1 multistage fractional crystallization. The reaction steps of the method are as follows: in the first step, the solvent anhydrous ethanol, n-propanol or n-Butanol is added to the plant sterol, and the temperature is raised to dissolve, and then the temperature is slowly lowered to crystallize and filtered, the obtained crystalline matter is subjected to the above concentration step 0 to 1 times, followed by centrifugal separation and vacuum drying. In the second step, a separation solvent is added to the phytosterol concentrate obtained in the first step, and the mixture is dissolved by heating up, then, the crystals were slowly cooled and filtered, and the obtained crystals were subjected to the above separation step 2 to 3 times. The invention greatly improves the purity and yield of stigmasterol through two separate steps of concentration and separation and purification of raw materials, and has no pollution to the environment. 2.2 polar solvent crystallization method stigmasterol was first enriched to 90% with non-polar solvent, and then crystallized with polar solvent to obtain high purity stigmasterol. The process is to dissolve the raw material in toluene to prepare 25% solution, cooled to 25 ° C., constant temperature 1H, crystallization, repeated 6 times to obtain 92% purity stigmasterol. When the purity of stigmasterol is more than 90%, it can no longer be enriched by crystallization method. At this time, the obtained stigmasterol is dissolved in acetone under anhydrous condition, the ratio is 1: 20, and it is cooled slowly, crystallization, the purity can be increased to 98%. 2.3 organic solvent crystallization method with mixed phytosterols as raw materials, the separation and crystallization characteristics of stigmasterol in toluene, toluene methanol and toluene acetone were studied. The results showed that the content of stigmasterol was more than 70% and the total yield of stigmasterol was more than 50% with toluene (90%) and acetone (10%) as mixed solvent after 5 times of crystallization. Gao Yuying, et al, enriched stigmasterol from soybean mixed phytosterol with n-butanol as solvent, solid-liquid ratio 1:4, and placed in constant temperature water bath between 20 ℃ and 30 ℃, crystallization 1~2h after constant temperature filtration or centrifugation, 4~5 grade crystallization to obtain more than 85% of the content of stigmasterol. |
| preparation method | mixed phytosterols is an important research topic in the large-scale production of single-component high-purity phytosterols, the separation and purification of mixed phytosterols can provide a relatively low cost for the production of steroidal drugs. Common extraction and separation methods are the following ways: 1 with ethyl acetate as extraction agent, soybean oil as raw material, using ultrasonic assisted extraction of soybean oil stigmasterol, on the basis of single factor experiment, the extraction process was optimized by orthogonal test L9(34). The results showed that the optimum extraction conditions of stigmasterol from soybean oil were as follows: Ultrasonic temperature 50 ℃, Ultrasonic, ultrasonic time 40min and liquid material ratio 19mL/g. Under the optimal conditions, the extraction rate of stigmasterol was the highest, reaching 34.15%. 2. Due to the extremely similar structure, it is a difficult and tedious task to separate and remove β-sitosterol, rapeseed sterol and campesterol from phytosterols to obtain high purity monosomal stigmasterol. In 1906, Windaus and Haith proposed the use of a chemical reaction of brominated acetates to achieve the enrichment of stigmasterol. Stigmasterol was refluxed in acetic anhydride to produce stigmasterol acetate. Then bromination with Excess bromine in dichloropropene to produce 5,6,22, 23-tetrabromostigmasterol acetate and 5, 6-dibromo β-sitosterol acetate, these two substances are slightly soluble or relatively soluble. Stigmasterol acetyl tetrabromide can be crystallized in ethanol, treated with zinc powder and then saponified, namely debromination and deacetylation treatment, so that stigmasterol regeneration. Finally, pure stigmasterol can be obtained by crystallization in acetone, so as to achieve the purpose of separation. references (1) solvent crystallization process comparison of stigmasterol separation and refining Guizhou chemical 2012.06(3)26-29 (2) research progress on extraction of stigmasterol from mixed phytosterols Yunnan chemical 2008.10(5)66-69 |
| Use | stigmasterol is mainly used as a raw material for the synthesis of steroid hormones, and can also be used as a raw material for the production of vitamin D3. Used in biochemical research, progesterone, is also a raw material for the manufacture of progesterone in medicine. The chemical scheme for progesterone production is shown below. FIG. 2 is a chemical reaction scheme for the preparation of progesterone from stigmasterol. It is used as a raw material for the synthesis of steroid hormones, and can also be used as a raw material for the production of vitamin D3 A phytosterol, whose chemical structure is similar to cholesterol. It has anti-cancer, anti-heat, anti-inflammatory and immunomodulatory effects. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:45:29
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