pregnenolone
(3b)-3-hydroxypregn-5-en-20-one
Identification
| Name | pregnenolone |
| CAS Number | 145-13-1 |
| EINECS | 205-647-4 |
| FDA UNII | 73R90F7MQ8 |
| Molecular Formula | C21 H32 O2 |
| Molecular Weight | 316.48444000 |
| MDL Number | MFCD00003628 |
| Nikkaji Number | J11.381F |
| Beilstein | 2059026 |
| XlogP3 | 4.20 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 192.00 °C. @ 760.00 mm Hg |
| Boiling Point | 443.26 °C. @ 760.00 mm Hg (est) |
| Flash Point | 372.00 °F. TCC ( 188.90 °C. ) (est) |
| logP (o/w) | 4.220 |
| Soluble in | water, 7.915 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD > 200 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | special dietary and nutritional additives |
| Recommendation for pregnenolone usage levels up to | not for fragrance use. |
| Recommendation for pregnenolone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-
dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
enelone
17b-(1-keto
ethyl)-D5-androsten-3b-ol
(3b)-3-
hydroxy-pregn-5-en-20-one
(3b)-3-
hydroxypregn-5-en-20-one
3b-
hydroxypregn-5-en-20-one
natolone
D5-
pregnen-3b-ol-20-one
pregnenolonum
PubMed:
Clinical Evaluation of Abiraterone in the Treatment of Metastatic Prostate Cancer.
PubMed:
The nuclear receptors pregnane X receptor and constitutive androstane receptor contribute to the impact of fipronil on hepatic gene expression linked to thyroid hormone metabolism.
PubMed:
Pregnenolone rescues schizophrenia-like behavior in dopamine transporter knockout mice.
PubMed:
Endocrine-disrupting effects of thioxanthone photoinitiators.
PubMed:
Abiraterone and other novel androgen-directed strategies for the treatment of prostate cancer: a new era of hormonal therapies is born.
PubMed:
Phytochemical composition and toxicity of an antioxidant extract from Pimpinella brachycarpa (Kom.) Nakai.
PubMed:
Endogenous steroid profiling by gas chromatography-tandem mass spectrometry and multivariate statistics for the detection of natural hormone abuse in cattle.
PubMed:
Development of an LC-MS/MS method to quantify sex hormones in bovine milk and influence of pregnancy in their levels.
PubMed:
Influence of gender, feeding regimen, and exposure duration on gene expression associated with xenobiotic metabolism in fathead minnows (Pimephales promelas).
PubMed:
Bisphenol A impairs follicle growth, inhibits steroidogenesis, and downregulates rate-limiting enzymes in the estradiol biosynthesis pathway.
PubMed:
Determination of naturally occurring progestogens in bovine milk as their oxime derivatives using high performance liquid chromatography-electrospray ionization-tandem mass spectrometry.
PubMed:
Effects of genistein and equol on human and rat testicular 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 activities.
PubMed:
Investigation of urinary steroid metabolites in calf urine after oral and intramuscular administration of DHEA.
PubMed:
The effect of ovarian steroids on oxytocin-stimulated secretion and synthesis of prostaglandins in bovine myometrial cells.
PubMed:
Metabolomics approach to anabolic steroid urine profiling of bovines treated with prohormones.
PubMed:
Chrysin, a natural flavonoid enhances steroidogenesis and steroidogenic acute regulatory protein gene expression in mouse Leydig cells.
PubMed:
Effects of adlay (Coix lachryma-jobi L. var. ma-yuen Stapf.) hull extracts on the secretion of progesterone and estradiol in vivo and in vitro.
PubMed:
Intrahippocampal allopregnanolone decreases voluntary chronic alcohol consumption in non-selected rats.
PubMed:
Effects of crude adlay hull acetone extract on corticosterone release from rat zona fasciculata-reticularis cells.
PubMed:
Human adrenocarcinoma (H295R) cells for rapid in vitro determination of effects on steroidogenesis: hormone production.
PubMed:
Downregulation of progesterone biosynthesis in rat granulosa cells by adlay (Coix lachryma-jobi L. var. ma-yuen Stapf.) bran extracts.
PubMed:
The neurosteroid pregnenolone sulfate neutralized the learning impairment induced by intrahippocampal nicotine in alcohol-drinking rats.
PubMed:
Intrahippocampal nicotine and neurosteroids effects on the anxiety-like behaviour in voluntary and chronic alcohol-drinking rats.
PubMed:
Influence of progesterone, pregnenolone and 17beta-hydroxyprogesterone on the function of bovine luteal cells treated with luteinizing hormone, noradrenaline and prostaglandin E2.
PubMed:
Non-genomic effect of steroids on oxytocin-stimulated intracellular mobilization of calcium and on prostaglandin F2alpha and E2 secretion from bovine endometrial cells.
PubMed:
Differential expression and function of beacon in the rat adrenal cortex and medulla.
PubMed:
Nuclear receptor, pregname X receptor, is required for induction of UDP-glucuronosyltranferases in mouse liver by pregnenolone-16 alpha-carbonitrile.
PubMed:
A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.
PubMed:
Steroid hormone receptors and dietary ligands: a selected review.
PubMed:
Effects of fasting on corticosterone production by zona fasciculata-reticularis cells in ovariectomized rats.
PubMed:
Thiazolidinediones influence plasma steroids of male obese Zucker rats.
PubMed:
Decreased expression of steroidogenic acute regulatory protein: a novel mechanism participating in the leptin-induced inhibition of glucocorticoid biosynthesis.
PubMed:
Age, body mass index, race and other determinants of steroid hormone variability: the HERITAGE Family Study.
PubMed:
Mechanism of action of noradrenaline on secretion of progesterone and oxytocin by the bovine corpus luteum in vitro.
PubMed:
Dehydroepiandrosterone and related steroids alter 3T3-L1 preadipocyte proliferation and differentiation.
PubMed:
Alteration of acetaminophen metabolism by sulfate and steroids in primary monolayer hepatocyte cultures of rats and mice.
PubMed:
Leptin modulates the glucocorticoid-induced ovarian steroidogenesis.
PubMed:
Influence of sampling on steroid hormone patterns of beef from bulls and steers.
PubMed:
The role of GABA-A and mitochondrial diazepam-binding inhibitor receptors on the effects of neurosteroids on food intake in mice.
PubMed:
Differences in natural steroid hormone patterns of beef from bulls and steers.
PubMed:
Effect of a dopamine agonist on luteinizing hormone receptors, cyclic AMP production and steroidogenesis in rat Leydig cells.
PubMed:
A positive role for thymus-derived steroids in formation of the T-cell repertoire.
PubMed:
A colorimetric assay method for 3beta-hydroxy-delta5-steroid dehydrogenase.
PubMed:
Aminoglutethimide, a corticosteroid synthesis inhibitor, facilitates brain stimulation reward in food-restricted rats: an investigation of underlying mechanisms.
PubMed:
The hyperphagic effect of 3 alpha-hydroxylated pregnane steroids in male rats.
PubMed:
Androgen biosynthesis in the stomach: expression of cytochrome P450 17 alpha-hydroxylase/17,20-lyase messenger ribonucleic acid and protein, and metabolism of pregnenolone and progesterone by parietal cells of the rat gastric mucosa.
PubMed:
The effect of colupulone (a HOPS beta-acid) on hepatic cytochrome P-450 enzymatic activity in the rat.
PubMed:
Enzymatic sulfation of glycosides and their corresponding aglycones by arylsulfate sulfotransferase from a human intestinal bacterium.
PubMed:
Effects of feed additives and veterinary drugs on aldosterone production and release by porcine adrenal cells in vitro.
PubMed:
The effects of pregnenolone on acquisition and retention of a food search task.
PubMed:
On the origin of vertebrate-type steroids present in Locusta migratoria: do they originate from the food?
PubMed:
Effects of cadmium and zinc on steroid metabolism and steroid level in the sea star Asterias rubens L.
PubMed:
Increased permeability of the rat biliary tree by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) treatment and protection by hepatoactive agents.
PubMed:
Mutagens in cooked foods--metabolism and genetic toxicity.