601-57-0
601-57-0
Chemical Structure
Cholestenone
Synonym(s): 4-Cholesten-3-one
- CAS No.: 601-57-0
- Formula:C27H44O
- Molecular Weight:384.64
IUPAC Name: (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
InChIKey: NYOXRYYXRWJDKP-GYKMGIIDSA-N
SMILES: CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O
Biological Activity: Cholestenone (4-cholesten-3-one) is an orally available antimicrobial agent that is metabolized primarily in the liver as an intermediate oxidation product of cholesterol. Cholestenone inhibits human dermal fibroblast migration and fights Helicobacter pylori infection in vitro and in mouse models by inhibiting cholesterol-α-D-glucopyranoside (CGL). Cholestenone also alleviates metabolic disorders caused by obesity in db/db mice[1][2][3][4].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Cholestenone | 99.95% | Cholestenone (4-cholesten-3-one) is an orally available antimicrobial agent that is metabolized primarily in the liver as an intermediate oxidation product of cholesterol. Cholestenone inhibits human dermal fibroblast migration and fights Helicobacter pylori infection in vitro and in mouse models by inhibiting cholesterol-α-D-glucopyranoside (CGL). Cholestenone also alleviates metabolic disorders caused by obesity in db/db mice. | ||||||||||||||||||||
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Cholestenone (Standard) | 98.68% | Cholestenone (Standard) (4-Cholesten-3-one (Standard)) is the analytical standard of Cholestenone (HY-113365). This product is intended for research and analytical applications. Cholestenone (4-cholesten-3-one) is an orally available antimicrobial agent that is metabolized primarily in the liver as an intermediate oxidation product of cholesterol. Cholestenone inhibits human dermal fibroblast migration and fights Helicobacter pylori infection in vitro and in mouse models by inhibiting cholesterol-α-D-glucopyranoside (CGL). Cholestenone also alleviates metabolic disorders caused by obesity in db/db mice. | ||||||||||||||||||||
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Cholestenone-d7 | Cholestenone-d7 is deuterium labeled Cholestenone. Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop | |||||||||||||||||||||
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Cholestenone-13C2 | 99.06% | Cholestenone-13C2 is the 13C labeled Cholestenone. Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells. | ||||||||||||||||||||
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Cholestenone-13C | 99.0% | Cholestenone-13C is the 13C labeled Cholestenone. Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells. | ||||||||||||||||||||
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Cholestenone-d5 | 98.04% | Cholestenone-d5 is the deuterium labeled Cholestenone. Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells. | ||||||||||||||||||||
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Deoxycorticosterone-d8 | 97.77% | Deoxycorticosterone-d8 is the deuterium labeled Deoxycorticosterone. Deoxycorticosterone is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid activity and acts as an aldosterone precursor. | ||||||||||||||||||||
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Δ4-Dafachronic acid | 96.93% | Δ4‑Dafachronic acid is an endogenous steroid hormone, an agonist of the DAF‑12 nuclear receptor, and a key ligand for the vitamin D receptor (VDR). Δ4‑Dafachronic acid promotes the active escape developmental trajectory in Austrofundulus limnaeus embryos even under diapause‑inducing conditions. Δ4‑Dafachronic acid is suitable for research on the developmental biology. | ||||||||||||||||||||
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(25R)-26-Hydroxycholest-4-en-3-one | 95.4% | (25R)-26-Hydroxycholest-4-en-3-one is an oxysterol. | ||||||||||||||||||||
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Epicholesterol-2,2,3,4,4,6-d6 | Epicholesterol-2,2,3,4,4,6-d6 is the deuterium labeled Epicholesterol-2,2,3,4,4,6. | |||||||||||||||||||||
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Cortodoxone-d5 | 99.90% | Cortodoxone-d5 is the deuterium labeled Cortodoxone. | ||||||||||||||||||||
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17α-Hydroxyprogesterone-d8 | 98.52% | 17α-Hydroxyprogesterone-d8 is the deuterium labeled 17α-Hydroxyprogesterone. 17α-Hydroxyprogesterone (17-Hydroxyprogesterone) is an endogenous progestogen as well as chemical intermediate in the biosynthesis of other steroid hormones, including the corticosteroids and the androgens and the estrogens. | ||||||||||||||||||||
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Cholesterol-d6-1 | 99.82% | Cholesterol-d6-1 is the deuterium labeled Cholesterol. Cholesterol is the major sterol in mammals. It is making up 20-25% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist. | ||||||||||||||||||||
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Cholesterol-d1 | 99.29% | Cholesterol-d1 is the deuterium labeled Cholesterol. Cholesterol is the major sterol in mammals. It is making up 20-25% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist. | ||||||||||||||||||||
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Progesterone-d9 | 99.93% | Progesterone-d9 is the deuterium labeled Progesterone. Progesterone is a steroid hormone that regulates the menstrual cycle and is crucial for pregnancy. | ||||||||||||||||||||
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Stigmasta-4,25-dien-3-one | Stigmasta-4,25-dien-3-one is a Steroids product that can be isolated from the herbs of Porcelia macrocarpa. | |||||||||||||||||||||
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β-Sitostenone | 95.0% | β-Sitostenone (Δ4-Sitosterol-3-one; β-Rosasterol oxide) is a sterol isolated from Cleistanthus eberhardtii. β-Sitostenone inhibits tyrosinase (tyrosinase) and cyclooxygenase (COX-1 and COX-2). β-Sitostenone has potential anti-melanogenic, anticancer, and anti-inflammatory activities. β-Sitostenone can be used in research on inflammation, cancer, and cosmetics. | ||||||||||||||||||||
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Sitosterone | Sitosterone is a steroid that can be isolated from stem bark of syzygium aqueum. Sitosterone shows cytotoxicity. | |||||||||||||||||||||
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4-Cholenic acid-3-one | 4-Cholenic acid-3-one is an antifeedant steroid metabolite formed via anaerobic biotransformation of Lithocholic acid (HY-B0172) by Pseudomonas sp. strain NCIB 10590. | |||||||||||||||||||||
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3-Oxo-4-cholestenoic acid | 3-Oxo-4-cholestenoic acid is a lipid that can be used to prepare lipid nanoparticles (LNPs) for drug delivery. | |||||||||||||||||||||
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Bisnoralcohol | 98.20% | Bisnoralcohol is a RANKL inhibitor with an IC50 of 2.325 μM. Bisnoralcohol can inhibit RANKL-induced osteoclastogenesis and exhibits antiosteoporosis activity. | ||||||||||||||||||||
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References
- [1]. unichi Kobayashi, et al. Cholestenone functions as an antibiotic against Helicobacter pylori by inhibiting biosynthesis of the cell wall component CGL. Proc Natl Acad Sci U S A. 2021 Apr 20;118(16):e2016469118. [Content Brief]
- [2]. Maarit Neuvonen, et al. Enzymatic oxidation of cholesterol: properties and functional effects of cholestenone in cell membranes. 2014 Aug 26;9(8):e103743. [Content Brief]
- [3]. G M TOMKINS, et al. Use of delta 4-cholestenone to reduce the level of serum cholesterol in man. Science. 1957 May 10;125(3254):936-7. [Content Brief]
- [4]. Mina Higuchi, et al. Dietary Cholest-4-en-3-one, a Cholesterol Metabolite of Gut Microbiota, Alleviates Hyperlipidemia, Hepatic Cholesterol Accumulation, and Hyperinsulinemia in Obese, Diabetic db/db Mice. Metabolites. 2024 Jun 3;14(6):321. [Content Brief]
