21-Hydroxypregnenolone
目录号 : GC33798
21-Hydroxypregnenolone是皮质酮合成的重要中间体。
Cas No.:1164-98-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
21-Hydroxypregnenolone is an essential intermediate in corticosterone synthesis.
[1]. Iudaev NA, et al. Pathways of corticosteroid biosynthesis in human adrenals (Itsenko-Cushing disease). Biokhimiia. 1976 Sep;41(9):1619-27.
| Cas No. | 1164-98-3 | SDF | |
| Canonical SMILES | C[C@]12[C@]([H])([C@]3([C@]([H])(CC2)[C@]4(C)C(C[C@H](CC4)O)=CC3)[H])CC[C@@H]1C(CO)=O | ||
| 分子式 | C21H32O3 | 分子量 | 332.48 |
| 溶解度 | Soluble in DMSO | 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 | 3.0077 mL | 15.0385 mL | 30.077 mL |
| 5 mM | 0.6015 mL | 3.0077 mL | 6.0154 mL |
| 10 mM | 0.3008 mL | 1.5038 mL | 3.0077 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。
A paradox: elevated 21-Hydroxypregnenolone production in newborns with 21-hydroxylase deficiency
Steroids 1987 Apr-May;49(4-5):295-311.PMID:3502660DOI:10.1016/0039-128x(87)90006-7.
21-Hydroxypregnenolone and its metabolite 5-pregnene-3 beta, 20 alpha 21-triol have been measured in the sulfate fraction of neonatal urine. These two steroids are the major two 21-hydroxylated 5-pregnenes produced by neonates and are almost exclusively excreted as disulfates. The excretions of these steroids by normal infants and infants with 21-hydroxylase deficiency were compared. In addition to measurement of the absolute excretion, the excretion relative to the total 3 beta-hydroxy-5-ene output was also determined. The results show that 21-Hydroxypregnenolone excretion is highly elevated in 21-hydroxylase deficiency (affected, mean 887 micrograms/24 h, range 453-1431 micrograms/24 h; normal, mean 117 micrograms/24 h, range 17-263 micrograms/24 h), but when compared to excretion of other delta 5 steroids the excretion is slightly low [(21-Hydroxypregnenolone + 5-pregnene-3 beta, 20 alpha, 21-triol)/total 3-beta-hydroxy-5-ene steroids, 2.9% affected; 3.6% normal]. This difference was not statistically significant. There is thus no evidence that the 21-hydroxylase acting on pregnenolone is deficient in congenital adrenal hyperplasia. The explanation of the normal activity of "pregnenolone 21-hydroxylase," although not clearly defined, is probably associated with two recent findings by other workers: (a) that the human fetus has an active 21-hydroxylase distinct from the adrenal enzyme and (b) that a 21-hydroxylase structurally very different from the adrenal enzyme, with high activity towards pregnenolone (but no activity towards 17-hydroxyprogesterone), has been isolated from rabbit hepatic microsomes.
Inhibition of human steroidogenic cytochrome P450 c17 by 21-Hydroxypregnenolone and related steroid hormones
Biol Pharm Bull 2012;35(9):1594-7.PMID:22975514DOI:10.1248/bpb.b12-00080.
The effects of 21-Hydroxypregnenolone and related steroids such as deoxycorticosterone (DOC; 21-hydroxyprogesterone), cortisol, and corticosterone on progesterone 17α-hydroxylase activity by steroidogenic cytochrome P450 c17 (CYP17) were investigated. 21-Hydroxypregnenolone contains a hydroxyl group at C3 in the A cyclic hydrocarbon ring and a double bond at C5 in the B cyclic hydrocarbon ring, whereas DOC, cortisol, and corticosterone contain a ketone group at C3 and a double bond at C4 in the A cyclic hydrocarbon ring. No marked inhibition was observed for DOC, cortisol, and corticosterone at 100 μM concentration. Nonetheless, 21-Hydroxypregnenolone exhibited competitive inhibition of progesterone 17α-hydroxylation activity by CYP17 with a Ki value of 36.4 µM. These results suggest that a hydroxyl group at C3 in the A ring and a double bond at C5 in the B ring in steroid hormones are important for the substrate recognition of CYP17.
Steroid 21-hydroxylation by human preovulatory follicles from stimulated cycles: a mass spectrometrical study of deoxycorticosterone, 21-Hydroxypregnenolone and 11-deoxycortisol in follicular fluid
J Steroid Biochem 1987 Mar;26(3):337-43.PMID:3495701DOI:10.1016/0022-4731(87)90098-7.
A highly specific technique based on gas chromatography-mass spectrometry associated with stable isotope dilution was applied to the analysis of follicular fluid aspirated from preovulatory follicles of women under ovarian stimulation prior to in vitro fertilization. Deoxycorticosterone, 21-Hydroxypregnenolone and 11-deoxycortisol have been identified and quantified in the nanomolar concentration range. Significant positive correlations were found between these 21-hydroxy-steroids and their immediate precursors, thus indicating a probable common cellular origin. Corticosterone was tentatively identified and cortisol was evidenced at concentrations lower than peripheral plasma levels. The occurrence in human follicular fluid of cortisol, together with different high concentration intermediates, constitutes evidence for ovarian intra-follicular 21-hydroxylase activity, and probably also for 11 beta-hydroxylation enzyme activity.
Unconjugated and sulfoconjugated steroids in plasma and zones of the adrenal cortex of the guinea pig
Steroids 1983 Jan;41(1):105-19.PMID:6581618DOI:10.1016/0039-128x(83)90021-1.
The following steroids were measured in their unconjugated and sulfoconjugated forms in plasma and in the outer and inner zones of the adrenal cortex of the guinea pig: pregnenolone, 17-hydroxypregnenolone, 21-Hydroxypregnenolone, dehydroepiandrosterone and deoxycorticosterone. In plasma, pregnenolone and 21-Hydroxypregnenolone were the predominant unconjugated steroids with concentrations 10-30 times higher than the other three steroids. Among the sulfoconjugated steroids, pregnenolone sulfate had a concentration 25-50 times higher than the other sulfoconjugates. For each steroid except 21-Hydroxypregnenolone the sulfoconjugated form was present in a concentration 2-7 times higher than the unconjugated form. In the adrenal cortex, the content of 21-Hydroxypregnenolone was significantly higher in the outer zone than in the inner zone and was present in amounts 3-100 times greater than the other unconjugated steroids in the outer zone. On the other hand, the content of pregnenolone was significantly greater in the inner zone than the outer zone, and was present in amounts 3-80 times greater than the other unconjugated steroids in the inner zone. With the exception of 21-Hydroxypregnenolone and deoxycorticosterone, the steroid sulfoconjugates were significantly higher in the inner cortical zone. As in plasma, pregnenolone sulfate was the most abundant sulfoconjugated steroid. This report also describes preliminary studies concerning sulfurylated hydroxyl groups in different positions of 21-Hydroxypregnenolone. The sulfoconjugate was prepared by using partially purified steroid sulfotransferase from the guinea pig adrenal. The results obtained indicated that of the total 21-Hydroxypregnenolone conjugate formed, approximately 40% was the 21-sulfate and 20% the 3-sulfate, whereas 40% was non-hydrolyzable with the techniques used and was not further characterized.
Soy-whey dual-protein alleviates osteoporosis of ovariectomized rats via regulating bone fat metabolism through gut-liver-bone axis
Nutrition 2022 Nov-Dec;103-104:111723.PMID:35843042DOI:10.1016/j.nut.2022.111723.
Objectives: Osteoporosis is increasingly prevalent, especially among postmenopausal women, both in China and worldwide. In previous work, soy-whey dual-protein (DP) intervention improved muscle status via regulation of gut microbiota. However, little information is available about the relationship between DP supplementation and osteoporosis. Methods: In this study, the ovariectomized rat model was used to detect the effect of DP on improving osteoporosis. Results: Significant improvement was observed in bone mineral density, bone microstructure, and bone biomechanics with both DP and zoledronic acid (positive control) intervention. DP supplementation dramatically reduced the levels of serum osteocalcin and parathyroid hormone in ovariectomized rats. Ingestion of DP also resulted in a significant decrease in the number of bone marrow adipocytes and a marked increase in the number of osteoblasts, accompanied by elevated expression of the key regulator osteoprotegerin at both mRNA and protein levels. In the analysis of fecal metabolites and intestinal microbiota, the fat metabolism-related molecules chenodeoxycholate, 21-Hydroxypregnenolone, and tetrahydrocorticosterone were markedly upregulated with DP treatment, whereas the content of fatty acids such as oleic acid were significantly downregulated. The abundance of three bacterial taxa (upregulated: Ruminococcaceae UCG_002; downregulated: anaerobic digester metagenome and Enterorhabdus) dramatically changed with DP intervention and was closely associated with fat metabolism-related metabolite content CONCLUSION: These results suggest that DP intervention could improve osteoporosis via regulation of bone marrow adipose tissue content and mesenchymal stem cell lineage differentiation. Furthermore, this effect might be mediated by the interaction between intestinal microbiota and metabolites.