21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione
(Synonyms: 21-羟基孕甾-1,4,9(11),16-四烯-3,20-二酮-21-醋酸酯) 目录号 : GC60467
21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione是delta9,11类固醇类合成的中间体(intermediate)，如Vamorolone 。delta9,11steroids是糖皮质激素的修饰后的产物，具有抗炎(anti-inflammatory)特性。delta9,11类固醇类可以用作保护细胞损伤(脂质过氧化)和抑制新生血管的试剂。
Cas No.:37413-91-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione is an intermediate of delta 9,11 steroids synthesis, for example, Vamorolone . The delta 9,11 steroids are modifications of glucocorticoids and has anti-inflammatory properties. The delta 9,11 steroids are agents for protection against cell damage (lipid peroxidation) and inhibition of neovascularization[1].
δ9,11 derivatives are designed and developed to stably incorporate into cell membranes and inhibit lipid peroxidation without glucocorticoid or mineralocorticoid activities, thus avoiding side effects associated with traditional corticosteroids[1].VBP15 acts as a lead compound due to potent NF-κB inhibition and GR translocation similar to prednisone and dexamethasone, lack of transactivation properties, and good bioavailability[1].
[1]. Erica K M Reeves, et al. VBP15: preclinical characterization of a novel anti-inflammatory delta 9,11 steroid. Bioorg Med Chem
| Cas No. | 37413-91-5 | SDF | |
| 别名 | 21-羟基孕甾-1,4,9(11),16-四烯-3,20-二酮-21-醋酸酯 | ||
| Canonical SMILES | C[C@@]12[C@](CC=C2C(COC(C)=O)=O)([H])[C@@]3([H])C([C@@]4(C(CC3)=CC(C=C4)=O)C)=CC1 | ||
| 分子式 | C23H26O4 | 分子量 | 366.45 |
| 溶解度 | DMSO: 100 mg/mL (272.89 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.7289 mL | 13.6444 mL | 27.2889 mL |
| 5 mM | 0.5458 mL | 2.7289 mL | 5.4578 mL |
| 10 mM | 0.2729 mL | 1.3644 mL | 2.7289 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
An Efficient Procedure for the Synthesis of 21-Acetoxypregna-1,4,9(11),16- tetraene-3,20-dione
Comb Chem High Throughput Screen 2020;23(3):225-231.PMID:32072895DOI:10.2174/1386207323666200219122644
Background: Halogenated corticosteroids are widely used in medicine, and the global need of these steroidal APIs is estimated to be 40 - 70 tons, annually. Vietnam currently imports the pharmaceutical compounds up to 90%, in particular 100% of steroidal drugs. Currently, industrial production is based on the chemical syntheses of corticosteroids from either 16- dehydropregnenolone acetate (obtained from diosgenin) or androstenedione (obtained from phytosterol). The development of shorter synthetic schemes and more economically feasible technologies is of great significance. Introduction of 1(2)-double bond at the final stages of the corticosteroids synthesis results inpoor yield. 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione (tetraene acetate) is a key intermediate in the synthesis of highly active halogenated corticosteroids such as dexamethasone and other halogenated corticosteroids. 21-acetoxypregna-1,4,9(11),16- tetraene-3,20-dione is a key intermediate in the synthesis of dexamethasone from the readily available and cheap 9α-hydroxyandrost-4-ene-3,17-dione. Objective: The purpose of this study was the development of an efficient and shorter procedure for the synthesis of 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyandrostenedione, which is a product of a bio-oxidative degradation of the side chain of phytosterols. Methods: Pregnane side chain was constructed using cyanohydrin method. For 1(2)- dehydrogenation, selene dioxide was applied for the introduction of Δ1(2)-double bond. Other stages of the synthesis were epimerization, Stork's iodination procedure and dehydration. Result: 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione was prepared from 9α- hydroxyandrostenedione in yield more than 46%. Conclusion: An efficient and practically feasible procedure for the synthesis of 21-acetoxypregna- 1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyandrostenedione, a key intermediate for the synthesis of 9-haloidated corticoids, has been developed. The procedure can be applied for the production of value-added 9-haloidated corticoids.