Pregnenolone - CAS 145-13-1
Catalog number: 145-13-1
Category: Inhibitor
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Molecular Formula:
C21H32O2
Molecular Weight:
316.48
COA:
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Targets:
mAChR
Description:
Pregnenolone is an endogenous steroid hormone for inhibition of M1 receptor- and M3 receptor-mediated currents with IC50 of 11.4 μM and 6.0 μM, respectively.
Purity:
>98%
Synonyms:
Pregnenolone; NSC 1616; NSC 18158; NSC-1616; NSC18158; NSC1616; NSC-18158; Prenolon; Regnosone; Skinostelon; Enelone; Natolone; Pregnetan; Pregneton; Pregnolon.
MSDS:
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InChIKey:
ORNBQBCIOKFOEO-QGVNFLHTSA-N
InChI:
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
Canonical SMILES:
CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
1. Ultrasound-enhanced enzymatic hydrolysis of conjugated female steroids as pretreatment for their analysis by LC–MS/MS in urine
B. Alvarez-Sanchez, F. Priego-Capote* and M. D. Luque de Castro. Analyst, 2009, 134, 1416–1422
Progesterone is the most abundant progestogen in metabolism, secreted by the corpus luteum and the placenta. Progesterone is required in embryo implantation, pregnancy maintenance and the development of mammary tissue for milk production. Progesterone is also an intermediate in the steroidogenesis of estrogens, androgens and adrenal corticosteroids. Pregnenolone, the metabolic precursor of progesterone, belongs to the group of neurosteroids, which are found in high concentrations in certain areas in the brain, where they affect the synaptic functioning, are neuroprotective and enhance myelinization. Furthermore, pregnenolone potentially improves cognitive and memory functioning.
2. Rhodium-catalyzed redox allylation reactions of ketones
Florence J. Williams, Robin E. Grote and Elizabeth R. Jarvo*. Chem. Commun., 2012, 48, 1496–1498
With the knowledge that the reaction conditions were mild and neutral, we sought to examine more complex ketones to probe functional group tolerance and highlight the utility of the method for more difficult reactions of synthetic intermediates (Scheme 2). Pregnenolone acetate was chosen as a sterically encumbered ketone containing an a-stereocenter (eqn (2)). With a simple increase in equivalents of allyl acetate and a longer reaction time, homoallylic alcohol 5 was obtained in good yield and with high diastereoselectivity (10 : 1). No epimerization was observed, implying that no enolization occurred under the reaction conditions.
3. Exploratory investigation of plasma metabolomics in human lung adenocarcinoma
Tao Wen, Liang Gao, Choon Nam Ong*. Mol. BioSyst., 2013, 9, 2370—2378
Sulfates of three sex hormones, testosterone, androsterone and pregnenolone, were significantly decreased in the plasma of lung adenocarcinoma patients relative to healthy controls. Testosterone is a male sex hormone produced mainly in the testes, but also by the ovaries and adrenal cortex. Androsterone is also a male sex hormone produced by metabolism of testosterone. Pregnenolone is a female sex hormone synthesized from cholesterol. Indeed, either male or female sex hormones are found in men and women, but their levels may vary a lot. To obtain a robust list of metabolites, we further analyzed these data by establishing a linear regression model, as described in the methods, to remove potentially influencing factors such as age, gender or smoking habits on the alterations of identified metabolites. Thus, the decreased trend of sex hormone sulfates in patients with lung adenocarcinoma is likely to be disease-related.
4. Direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids
Dhevalapally B. Ramachary,* Rajasekar Sakthidevi and P. Srinivasa Reddy. RSC Adv., 2013, 3, 13497–13506
The steroid pregnadienolone-3-acetate 3g under Pd/C mediated transfer hydrogenation with 2a (Condition-9) yielded the product pregnenolone-3-acetate 4g with >99% de as an inseparable mixture with pyridine byproduct (Table 3, entry 5). Later, the mixture was deacetylated and the de/relative stereochemistry of the reaction was unambiguously deter- mined through comparing with pregnenolone. Interestingly, Pd/C–Hantzsch ester mediated transfer hydrogenation of dienone containing steroids 3h, 3j and trienone-containing steroid 3l resulted in a mixture of totally hydrogenated products 4h, 4j, and 4l as major products and also partially hydrogenated enones 3i and 3k as minor products. The use of lower equiv. of 2a on the above reactions also could not perform the stereoselective product generation (Table 3, entries 6–8). Resulting 5b-3-ketosteroids 4 are synthetically and medicinally useful precursors as shown in Chart 1, especially the product pregnenolone-3-acetate 4g which has been used as an important precursor in the synthesis of vitamin D3, inhibitors of ecdysone and potent anti-tumor reagents.
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Chemical Structure

CAS 145-13-1 Pregnenolone

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