SESAMIN(RG)
Sesamin
CAS: 607-80-7
Molecular Formula: C20H18O6
SESAMIN(RG) - Names and Identifiers
| Name | Sesamin |
| Synonyms | Sezamin Sesamin Fagarol d-Sesamin NSC 36403 AI3-00811 SesameP.E. Episesamin SESAMIN(P) SESAMIN(RG) (+)-Sesamin D-(+)-Sesamin Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furan 5,5'-(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(1,3-benzodioxole) 1H,3H-Furo(3,4-c)furan, tetrahydro-1,4-bis(3,4-(methylenedioxy)phenyl)-, (1S,3aR,4S,6aR)- 1,3-Benzodioxole,5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-,[1S-(1α,3aα,4α, 6aα)]- 1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-, [1S-(1a,3aa,4a,6aa)]- 1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)bis-, (1S-(1alpha,3a alpha,4alpha,6a alpha))- [1S-(1BETA,3ALPHA-BETA,4BETA,6ALPHA-BETA)]-5,5'-(TETRAHYDRO-1H,3H-FURO[3,4-C]FURAN-1,4-DIYL)BIS-1,3-BENZODIOXOLE |
| CAS | 607-80-7 |
| InChI | InChI=1/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1 |
| InChIKey | PEYUIKBAABKQKQ-AFHBHXEDSA-N |
SESAMIN(RG) - Physico-chemical Properties
| Molecular Formula | C20H18O6 |
| Molar Mass | 354.35 |
| Density | 1.385±0.06 g/cm3(Predicted) |
| Melting Point | 121.0 to 125.0 °C |
| Boling Point | 504.4±50.0 °C(Predicted) |
| Specific Rotation(α) | +64.5°(c=1.75，chloroform) |
| Flash Point | 212.3°C |
| Solubility | Soluble in chloroform, benzene, acetic acid, acetone, slightly soluble in ether, petroleum ether. Almost insoluble in water, alkaline solution and hydrochloric acid. |
| Vapor Presure | 8.38E-10mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White |
| Merck | 14,8470 |
| Storage Condition | -20°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| Refractive Index | 1.622 |
| MDL | MFCD00216134 |
| Physical and Chemical Properties | White needle-like crystals, soluble in methanol, ethanol, DMSO and other organic solvents, from sesame cake, Paulownia tomentosa. |
SESAMIN(RG) - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29329990 |
SESAMIN(RG) - Reference
| Reference Show more | 1. Su Wangcang, Hao hongdan, Xu Hongle, Sun Lanlan, Wu Renhai. Synergistic effect and safety of ten kinds of adjuvants on herbicide tobacco, nitrate and thallium in corn field [J]. Henan Agricultural Sciences 2019 48(08):95-101. 2. Ren Yuanyuan, Li Shuguo, Zhang Yunhuan. Antioxidant activity of sesamin in soybean oil [J]. Food industry, 2017, 038(012):118-122. 3. Fang Longyun, Cheng Lin, Zhou Lulin, etc. Effects of sesamin on contractile function of isolated toad myocardium and its mechanism [J]. Medical Journal of Yanbian University, 2014, v.37;No.143(004):266-267. 4. Ren Yuanyuan, Li Shuguo, Yan Yawei, et al. Extraction of sesamin and sesamin crystallization from sesame by ultrasonic-assisted response surface method [J]. Food Science and Technology, 2016, 29 (12):208-212. 5. Li Shujun, Liu Peng, fu wisdom, etc. Changes of sesamin content and antioxidant activity of black sesame before and after processing [J]. Specialty research, 2016(4). 6. Zhang Dong, Duan Zhang Qun, Li Xiu-Juan, Zhu Lin, Xue Yalin. Simultaneous determination of tocopherol, sesamin and sesamin in sesame oil by normal phase high performance liquid chromatography [J]. China grease, 2018,43(05):131-134. 7. Liu Jie, Liu Guangxue, Shang Mingying, et al. Identification of HPLC characteristic chromatograms of Asarum and Asarum and analysis of anti-inflammatory targets and anti-inflammatory components [J]. Chinese Journal of Traditional Chinese Medicine, 2020 v.45(06):168-177. 8. Liu Luma Jin and Shen Xiaomei et al. Determination of five soybean isoflavones and sesamin in a health wine by ultra performance liquid chromatography [J]. Wine 2019 046(004):86-88. 9. Chen, Yazhen, et al. "Effects of thermal preparation and in vital." Food and Chemical Biology 128 (2019): 89-96.https:// doi.org/10.1016/j. FCT. 3/054, 2019 10. Chen, Yazhen, et al." Effect of roasting and in vitro digestion on phenolic profiles and antioxidant activity of water-soluble extracts from sesame." Food and Chemical Toxicology 139 (2020): 111239.https://doi.org/10.1016/j.fct.2020.111239 11. [IF=4.932] Ching-Huei Lin et al."The effect of sesamin on airway fibrosis in vitro and in vivo."Int Immunopharmacol. 2014 Sep;22:141 12. [IF=2.74] Ching-Huei Lin et al."Protective Effects of the Polyphenol Sesamin on Allergen-Induced TH2 Responses and Airway Inflammation in Mice."Plos One. 2014 Apr;9(4):e96091 13. [IF=6.023] Yazhen Chen et al."Effects of thermal preparation and in vitro digestion on lignan profiles and antioxidant activity in defatted-sesame meal."Food Chem Toxicol. 2019 Jun;128:89 14. [IF=6.023] Yazhen Chen et al."Effect of roasting and in vitro digestion on phenolic profiles and antioxidant activity of water-soluble extracts from sesame."Food Chem Toxicol. 2020 May;139:111239 15. [IF=5.81] Dong-Mei Hai et al."Protective Effects of Sesamin on Cytoxan-Induced Spermatogenesis Dysfunction by Regulating RNF8-ubH2A/ubH2B Pathways in Male Mice."Front Pharmacol. 2021; 12: 708467 |
SESAMIN(RG) - Reference Information
| Introduction | Sesamin is a natural ingredient contained in sesame seeds, which contain about 0.3-0.5% sesamin. Sesamin has excellent antioxidant effect, can be anti-aging, regulate blood lipids, protect the liver, lower blood pressure, anti-cancer, regulate immunity, make the hair black and bright and many other physiological effects. In human experiments, it is proved that sesamin can be transported to the liver and metabolized into antioxidant substances in the liver, and the antioxidant effect is stronger than that of vitamin E. |
| preparation | take 1L of sesame oil foot (965.8g), add 4L of anhydrous ethanol, the mixture was stirred at 30 ° C. For 5H, allowed to stand and layered, the supernatant was taken and rotary evaporated to obtain sesamin enrichment. Anhydrous methanol was added to the sesamin enrichment, the solid-liquid ratio of sesamin enrichment and anhydrous methanol was 1 ∶ 4(kg/L), and the leaching solution was obtained at 55 ℃ for 3H, the amount of activated carbon was 1% of the mass of the leaching solution, stirred for 0.5h, and then filtered to obtain the sesamin extract. The sesamin extract was slowly cooled to -10 C, and the sesamin was crystallized for 2h, the crude sesamin was obtained by filtration. Petroleum ether was added to the crude sesamin, and the ratio of the crude sesamin to petroleum ether was 1 ∶ 1(kg/L), and the mixture was closed at 35 ℃ for 0.5h, the crude sesamin was obtained by filtration. The crude sesamin was dissolved in anhydrous ethanol, and the ratio of crude sesamin to anhydrous ethanol was 1:30(kg/L), time to maintain 3 hours, in this condition after 2 times crystallization, vacuum drying to obtain sesamin product 2.16g, sesamin extraction rate 89.1%, and the purity of the obtained sesamin product was 92.1%. |
| Content determination | a method for determining the content of sesamin in sesame seeds, comprising the following steps:(1) preparation of sesamin standard solution: weigh 10mg of sesamin standard, add anhydrous methanol to dissolve and dilute to 50mL, then filter with 0.45 μm filter membrane to obtain 0.2mg/ mL of sesamin standard solution;(2) draw the standard curve of sesamin: take 20, 10, 5, 4, 2, 0.8 of the sesamin standard solution obtained in step (1), and add anhydrous methanol 0, 10, 15, 16, 18, 19.2mL, shake to prepare the methanol solution of sesamin standard with gradient concentration of 200, 100, 50, 40, 20, 8ug/mL, the above solutions were analyzed by liquid chromatography, and the standard curve of sesamin was drawn according to the determination results (the liquid chromatogram of sesamin standard solution is shown in Figure 1), the linear relationship equation between the content of sesamin and the peak area is obtained: A = 587.525675x-4.531582, where A is the peak area and x is the content of sesamin;(3) prepare the sample solution to be tested: using Yuzhi No. 11 sesame seeds as the sample to be tested, the sesame seeds to be tested were crushed by a universal pulverizer for 30s, then sieved through a sieve of 0.35 μm, and 0.2g of the obtained sesame powder sample was taken, add 100% ethanol 5ml;(4) ultrasonic treatment and filtration: the mixed solution obtained in step (3) in 30 ~ Under the condition of 60 ℃, ultrasonic treatment was carried out for 20~50min, and then the solution after ultrasonic treatment was filtered with 0.45 μm filter membrane, the model is KQ3200DE CNC ultrasonic cleaner, ultrasonic processing is carried out under the ultrasonic power of 70~100W. (5) detection: Take 9 μl of the filtrate obtained in step (4), use liquid chromatography to detect the filtrate, according to the standard curve of sesamin, the content of sesamin in sesame seeds was calculated by the linear equation. |
| Use | sesamin has the effects of regulating blood pressure and blood lipid, protecting and strengthening liver function, antioxidation and inhibiting tumor. non-competitive Δ5-desaturase inhibitors. |
Last Update：2024-04-09 15:16:51
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