479-98-1
1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside
CAS: 479-98-1
Molecular Formula: C15H22O9
479-98-1 - Names and Identifiers
479-98-1 - Physico-chemical Properties
| Molecular Formula | C15H22O9 |
| Molar Mass | 346.33 |
| Density | 1.61±0.1 g/cm3(Predicted) |
| Melting Point | 181° |
| Boling Point | 669.0±55.0 °C(Predicted) |
| Specific Rotation(α) | D21 -163.1° (c = 1.6) |
| Flash Point | 358.414°C |
| Solubility | Soluble in water, ethanol and methanol, almost insoluble in chloroform, ether and petroleum ether. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White needle crystal (ethanol) |
| BRN | 50340 |
| pKa | 12.80±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.66 |
| MDL | MFCD00136026 |
| Physical and Chemical Properties | Soluble in water, ethanol and methanol, almost insoluble in chloroform, ether and petroleum ether. From eucommia ulmoides, plantain, Rehmannia and other Chinese herbal medicines. |
479-98-1 - Risk and Safety
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-23 |
479-98-1 - Reference
| Reference Show more | 1. Xu Dodo, Peng Huanhuan, Jiang Meifang, etc. LC-LTQ-Orbitrap analysis of chemical constituents of extract from radix scrophulariae and its transitional components in rat plasma [J]. Chinese Journal of Traditional Chinese Medicine, 2016, 41(003):521-527. 2. Lan, Ji, Yan, Liu, ze, Zhang, Qin, Pei, Chen, Li, Bao, Hui. Differences and dynamic changes of growth characteristics and main effective components in leaves of Eucommia ulmoides Oliv. From different habitats [J]. Journal of Agricultural University of Hebei 2019 42(01):51-56. 3. Zhou Binwen, Zhong Xiaoming, Huang Zhen. Optimization of heat reflux extraction of iridoid glycoside from radix scrophulariae [J]. Chinese traditional medicines, 2018, 040(006):1292-1297. 4. Liu Fang, Huang Xiaojie, Lin Meilan, etc. Study on the grade quality of radix scrophulariae [J]. New Traditional Chinese Medicine and Clinical Pharmacology, Volume 31, 20208, pages 2020-983, ISTIC PKU CSCD CA. 5. He Shiru, Li Li, Xu Guang Ming, etc. Rapid determination of effective components in radix scrophulariae by solid phase extraction and high performance liquid chromatography [J]. Asia-Pacific traditional medicine, 2020, 016(001):54-57. 6. Li Li, Zhou, Jiang, Yuan, Zhi, Ying, et al. Determination of five index components in radix scrophulariae by dispersive solid phase extraction and HPLC [J]. Strait pharmacy 2019 031(011):30-33. 7. Wei Jin-jin, Xin Donglin, Chen Xiang, et al. Effect of steam explosion pretreatment on the extraction of active components and gum from eucommia ulmoides bark [J]. Chemistry and Industry of forest products, 2019, 39(1):88-94. 8. Du Qingxin, Wei Yanxiu, Liu Panfeng, et al. Diversity of main active components in male flowers of Eucommia ulmoides Oliv. [J]. Forest Science, 2017, 053(002):35-43. 9. Du Qingxin, Wei Yanxiu, Li Qin, et al. Dynamics of Growth and development and changes of active components in male flowers of Eucommia ulmoides Oliv. [J]. Chinese herbal medicine, 2017, 048(013):2746-2751. 10. Du Qingxin, Liu Panfeng, Wei Yanxiu, Qingjun, Du Hongyan. Comprehensive Evaluation of Eucommia male flower quality based on principal component and cluster analysis [J]. Journal of Plant Research, 2016,36(06):846-852 859. 11. Liu Min, Wang Jianying, Wei Li, Pan Yingyi, Yuan Ying. Determination of eight components in bark, leaf and male flower of Eucommia ulmoides Oliv. By HPLC [J]. Chinese traditional medicines, 2021,43(03):686-691. 12. [IF = 6.529] Qi Huang et al."Systematic investigation of the pharmacological mechanism for renal protection by the leaves of Eucommia ulmoides Oliver using UPLC-Q-TOF/MS combined with network pharmacology analysis."Biomed Pharmacother. 2021 Aug;140:111735 13. [IF=4.142] Wang Chenxi et al."Systematic quality evaluation of Peiyuan Tongnao capsule by offline two-dimensional liquid chromatography/quadrupole-Orbitrap mass spectrometry and adjusted parallel reaction monitoring of quality markers."Anal Bioanal Chem. 2019 Nov;4 14. [IF=3.701] Bo Ma et al."Aucubin alleviates diabetic nephropathy by inhibiting NF-κB activation and inducing SIRT1/SIRT3-FOXO3a signaling pathway in high-fat diet/streptozotocin-induced diabetic mice."J Funct Foods. 2020 Jan;64:103702 15. [IF=2.629] Guan Mengqi et al."The Aqueous Extract of Eucommia Leaves Promotes Proliferation, Differentiation, and Mineralization of Osteoblast-Like MC3T3-E1 Cells."Evid-Based Compl Alt. 2021;2021:3641317 16. [IF=1.902] Chenxi Wang et al."Multiple component-pharmacokinetic studies on 10 bioactive constituents of Peiyuan Tongnao capsule using parallel reaction monitoring mode."Biomed Chromatogr. 2021 Oct;35(10):e5153 17. [IF=3.503] Yongfeng Zhang et al.Aucubin slows the development of osteoporosis by inhibiting osteoclast differentiation via the nuclear factor erythroid 2-related factor 2-mediated antioxidation pathway.Pharm Biol. 2021;59(1):1556-1565 18. [IF=3.352] Mi-jun Peng et al."Dietary supplementation Eucommia ulmoides extract high content served as a feed additive in the hens industry."Poultry Sci. 2021 Dec;:101650 19. [IF=4.451] Xue-song Wang et al."The antihypertensive effects of Eucommia ulmoides leaf water/ethanol extracts are chlorogenic acid dependent."Journal of Functional Foods. 2022 Jul;94:105129 |
479-98-1 - Reference Information
| Plant source: | Eucommia |
| overview | aucubin (Aucubin), also known as coral glycoside, chemical name β-D-glucopyranoside, bitter, soluble in water, ethanol, methanol, insoluble in chloroform, ether, petroleum ether and other solvents. This product is a kind of iridoid compound widely existing in many plant species in nature. It has the ability to clear dampness and heat, relieve urine, relieve pain, reduce blood pressure, protect liver and protect liver, anti-inflammatory, anti-tumor and other biological actives. It can promote stem cell regeneration and obviously inhibit the replication of hepatitis B virus DNA. Its aglycone and effective polymer are antibiotics. Since the discovery of the existence of aucubin in natural plant species, it has been successively found in plant species such as Garryaceae, Scrophulariaceae (Scrophulariaceae), Scrophulariaceae (Scrophulariaceae), Globulariaceae, Eucommiaceae (Eucommiaceae), etc. This compound has been found in the genus, and the content of planago and Eucommia is very high. The main source of aucubin is extracted from natural plants, and some people use tissue culture to extract aucubin from eucommia ulmoides callus. Fig. 1 is the structural formula of aucubin |
| Distribution and biosynthesis | Distribution of aucubin in plants mainly exists in Loniceraceae, Pteranaceae, and Eucommia plants. Traditional Chinese medicines containing aucubin include Eucommia, plantain, Rehmannia, Vitex, Scrophulariae, Taibaishen, etc. Among them, Eucommia leaves, skins, and seeds all contain aucubin, while the whole plant contains aucubin, and the rest contain aucubin in the roots. Taoleucoside not only exists in Chinese herbal medicine, but also in some flowers and fruits. Such as native to China's Taiwan and Japan, aucubin is an excellent indoor foliage plant, its chemical composition contains aucubin. The flowers, stems and leaves of jasmine contain iridoids, and aucubin is one of them. In addition, the third generation green fruit Lonicera edulis, which has the reputation of "fruit nutrition bank", also contains aucubin. Biosynthetic aucubin belongs to cyclopentene-type iridoid glycosides. This kind of compound is hydrolyzed from pyrophosphate to remove pyrophosphate in plants, and then oxidized to form citral. The latter is cyclized, double bond shift, hydration and oxidation to form Iant dialdehyde. Then, after enolization, Iant dialdehyde undergoes intramolecular condensation to form irene ether terpene alcohol, which then forms irene ether terpene glycosides. The main source of aucubin is extracted from natural plants, and some people use cell engineering methods to culture aucubin from the callus of Eucommia ulmoides. From an economic point of view, since most of the plants that can extract aucubin are cheap and easy to obtain, extracting aucubin from plants has more research and development prospects than other methods. |
| extraction and separation | 1. cold leaching extraction method: since aucubin is easily soluble in methanol, it is extracted with 30% methanol solution. When the room temperature is placed, the color of the solution changes. The higher the room temperature, the faster the change. When the sample is extracted, the sample is placed in the refrigerator overnight. The color of the sample solution remains unchanged, and then placed, there is no change. Therefore, the sample solution is stable after cold leaching with 30% methanol solution. The process is simple and economical, but the extraction time is long. 2. Alcohol extraction of lead salt precipitation method: extract with ethanol, concentrate the extract to prepare extract, then add water to dissolve, then add lead salt to precipitate, filter the precipitate, pass the filtrate into H2S to remove lead, reduce pressure After concentration, dissolve the residue with acetone, concentrate the acetone liquid to obtain a crude aucubin, and finally recrystallize to obtain a pure product. Because the lead precipitation method has a certain selectivity for aucubin, this method can obtain a relatively pure aucubin, but due to the use of toxic heavy metal lead, it may cause certain pollution to aucubin products. 3. Ultrasonic extraction method: Ultrasonic is a uniform spherical mechanical wave, with a unique form of action-cavitation produces a strong shock wave and micro-jet inside the liquid, which can crush the cell wall and make the intracellular components penetrate into the solution In order to achieve the purpose of separation. The ultrasonic extraction method is simple and fast to operate, has the advantages of saving time and no heating. It can be used to extract some substances that are easily destroyed and decomposed by heat, and has low comprehensive cost, low pollution, and easy separation of the extract, which can achieve better than conventional extraction. The method is more ideal. In addition, the method is simple and suitable for industrial production, but it is currently limited to laboratory scale. 4. Macroporous resin adsorption method: Macroporous adsorption resin is a kind of polymer adsorbent with macroporous structure without exchange groups, and it is also a lipophilic substance. It has the advantages of good selectivity, high mechanical strength, convenient regeneration treatment, fast adsorption speed, simple operation, stable product quality, low production cost, etc., so it is especially suitable for separation and purification of water-soluble compounds. However, this method takes a long time and is difficult to clean the adsorption resin. At present, the adsorption resins used to purify aucubin mainly include S-8 resin and D4020 resin. Among them, S-8 resin has good selectivity and large adsorption capacity. It can be completely eluted with 60% ethanol aqueous solution. |
| biological activity | aucubin has a wide range of biological activities, and the research on its biological activity in modern science has gone deep into many fields such as food, health care, medicine and daily chemical industry. 1. Anti-inflammatory and antiviral effects of aucubin has obvious hepatoprotective effects and can significantly inhibit the replication of hepatitis B virus DNA. Studies have shown that aucubin can significantly inhibit the increase of ALT and AST caused by liver injury caused by CCl4 in serum, and can prevent the decline of liver RNA synthesis level caused by α-amanthin. The use of aucubin or β-glucosidase alone does not show anti-hepatitis B virus activity, but when the two are pre-insulated, they show strong anti-hepatitis B virus activity. It does not have antiviral effect by itself, but when it is precultured with glucosidase, it will produce obvious antiviral effect. 2. Anti-oxidation and anti-aging effect Free radicals are toxic substances that damage themselves continuously produced in the process of body metabolism. The free radicals in the human body are mainly oxygen free radicals, which can peroxidize the unsaturated fatty acids on the cell membrane, destroy the biological membrane structure, and form lipofuscin, which is one of the main characteristics of aging. Li Farong and others studied the scavenging effect of aucubin on free radicals produced in chemical systems and its protective effect on oxidative damage to tissue homogenates, mitochondria, and microsomes. Collagen is a kind of high molecular protein. Its filamentous collagen fibers can make skin strong and elastic. With the increase of age, human collagen will gradually lose, skin will gradually lose elasticity and become thinner and aging, and a series of aging phenomena such as stains and wrinkles will appear. Studies have found that Eucommia ulmoides leaves water extract and methanol extract can promote collagen synthesis and achieve the purpose of anti-aging. The best experimental group extract contains a large amount of aucubin. 3. Other bioactive aucubin has obvious antihypertensive effect, long-lasting antihypertensive without any adverse reactions, and has a two-way regulation function on blood pressure, which is unmatched by chemical antihypertensive drugs. Eucommia leaf extract powder has anti-fatigue effect, and it contains aucubin. Sapocin can stimulate the parasympathetic center, accelerate the transfer and elimination of uric acid, and there is no "rapid tolerance" phenomenon; it can also antagonize the uterine contraction caused by acetylcholine in vitro; it also has anti-tumor activity. |
| application | 1. a considerable number of proprietary Chinese medicines with heat clearing, diuresis, blood pressure lowering and liver protection included in the "drug standards" of the Ministry of health of the medical and health industry contain aucubin and are the main components. Such as Eucommia ulmoides tablet, has a variety of pharmacological effects such as antihypertensive, diuretic, antibacterial, antiviral, anti-aging, and its main component is aucubin. At present, in the production of compound litchi grass granules and other drugs, aucubin has been taken as one of the important indicators of quality control. The eucommia health tea with eucommia leaves as the main ingredient has the functions of clearing away heat and detoxification, reducing blood pressure and reducing fat, losing weight and strengthening body. 2. Daily chemical industry With the enhancement of consumption awareness and the improvement of consumption level, hairdressing products have become people's daily consumption necessities from luxury goods. Because Chinese herbal medicine often has both nutritional and curative effects, and the effect is mild, it is very suitable as a cosmetic additive. The aucubin, which is widely found in Chinese herbal medicines, can react with amino acids to form colored products, and can also be decomposed by dilute acids and enzymes. Depending on its dosage, it can generate brown-black to black dendritic polymer precipitates. The hair fiber has strong adhesion, natural color, no irritation to the skin, and is a permanent hair dye. 3. Japanese scholars in the feed industry have concluded in recent years that Eucommia ulmoides is a rich feed additive. Eucommia ulmoides leaf powder mixed into livestock, poultry and fish feed can improve their immunity and reduce the occurrence of diseases. This is because adding a substance containing aucubin to the feed can inhibit the growth of Gram-negative and positive bacteria and reduce the loss of nutrients. (2016-01-13) |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has the effects of clearing dampness and heat, urinating, analgesia, lowering blood pressure, protecting liver and liver, and anti-tumor. It can promote stem cell regeneration and obviously inhibit the replication of hepatitis B virus DNA. |
Last Update：2024-04-09 21:54:55
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Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Multiple SpecificationsSpot supply
Product Name: Aucubin (Standard) Visit Supplier Webpage Request for quotationCAS: 479-98-1
Tel: 609-228-6898
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Tel: +86-400-900-4166
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Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
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479-98-1
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118994-84-6
175276-50-3
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