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6beta-Hydroxystigmast-4-en-3-one

CAS# 36450-02-9

6beta-Hydroxystigmast-4-en-3-one

2D Structure

Catalog No. BCN5322----Order now to get a substantial discount!

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Quality Control of 6beta-Hydroxystigmast-4-en-3-one

3D structure

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6beta-Hydroxystigmast-4-en-3-one

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Chemical Properties of 6beta-Hydroxystigmast-4-en-3-one

Cas No. 36450-02-9 SDF Download SDF
PubChem ID 71307329 Appearance Cryst.
Formula C29H48O2 M.Wt 428.7
Type of Compound Steroids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-6-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
SMILES CCC(CCC(C)C1CCC2C1(CCC3C2CC(C4=CC(=O)CCC34C)O)C)C(C)C
Standard InChIKey IWNCBADONFSAAW-ATPUVMSWSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 6beta-Hydroxystigmast-4-en-3-one

The herbs of Phaseolus vulgaris

Biological Activity of 6beta-Hydroxystigmast-4-en-3-one

In vitro

Chemical constituents from branch of Macaranga adenantha and their TNF-α inhibitory activity.[Reference: WebLink]

China Journal of Chinese Materia Medica, 2007, 32(12):1175-1179.

To investigate the chemical constituents of the brach of Macaranga adenantha, and evaluate their TNF-alpha inhibitory activity.
METHODS AND RESULTS:
The chemical conshifuents were isolated and purified by chromatographic methods. Structures of the compounds were identified by spectroscopic methods. The TNF-alpha secretion inhibitory activity of the mouse peritoneal macrophages was evaluated by MTT methods. Ten compounds were isolated and their structures were identified as: cleomiscosin A (1), cleomiscosin B (2), ellagic acid 4-O-alpha-D-rhamnopyranside (3), ellagic acid 4-O-beta-D-xylopyranoside (4), vanillic acid (5), (24R) -stigmast-4-en-3-one (6), (24R) -stigmast-3, 6-dione (7), (24R) -6beta-hydroxy-stigmast-4-en-3-one (6beta-Hydroxystigmast-4-en-3-one ,8), daucosterol (9), beta-sitosteryl glucoside-6'-O-heptadecoicate (10). At a concentration of 10 micromol x L(-1), compounds 1, 3 and 4 showed inhibitory activity to TNF-alpha secretion of the mouse peritoneal macrophages with the inhibitory rates of 57.0%, 64.4%, and 57. 4%, respectively.
CONCLUSIONS:
All compounds were isolated from genus Macaranga for the first time. Compounds 1, 3, and 4 were active against TNF-alpha secretion of the mouse peritoneal macrophages.

Protocol of 6beta-Hydroxystigmast-4-en-3-one

Structure Identification
Phytochemistry, 1973, 12(4):903-906.

6β-Hydroxy-4-stigmasten-3-one and 6β-hydroxy-4-campesten-3-one.[Reference: WebLink]


METHODS AND RESULTS:
The first naturally occurring 6-hydroxylated Δ4-3-oxo steroids with intact sterol side chains have been isolated as a molecular complex from the bark extracts of Melia azedarach L. The complex has been characterized by UV, IR, NMR and MS analyses to consist of 6β-hydroxy-4-stigmasten-3-one(6beta-Hydroxystigmast-4-en-3-one) and 6β-hydroxy-4-campesten-3-one, and these structures confirmed by partial synthesis.

6beta-Hydroxystigmast-4-en-3-one Dilution Calculator

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Preparing Stock Solutions of 6beta-Hydroxystigmast-4-en-3-one

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3326 mL 11.6632 mL 23.3263 mL 46.6527 mL 58.3158 mL
5 mM 0.4665 mL 2.3326 mL 4.6653 mL 9.3305 mL 11.6632 mL
10 mM 0.2333 mL 1.1663 mL 2.3326 mL 4.6653 mL 5.8316 mL
50 mM 0.0467 mL 0.2333 mL 0.4665 mL 0.9331 mL 1.1663 mL
100 mM 0.0233 mL 0.1166 mL 0.2333 mL 0.4665 mL 0.5832 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 6beta-Hydroxystigmast-4-en-3-one

Secondary metabolites and antimycobacterial activities from the roots of Ficus nervosa.[Pubmed:20658670]

Chem Biodivers. 2010 Jul;7(7):1814-21.

Bioassay-guided fractionation of the active AcOEt-soluble layer led to the isolation of two new pyranocoumarins, 3-hydroxyxanthyletin (1) and 3-methoxyxanthyletin (2), along with 22 known compounds including four simple coumarins, i.e., xanthyletin (3), umbelliferone (4), scopoletin (5), and (+)-(S)-marmesin (6); nine flavonoids, i.e., carpachromene (7), parvisoflavone B (8), alpinumisoflavone (9) genistein (10), 2'-hydroxygenistein (11), prunetin (12), cajanin (13), apigenin (14), and (2S)-naringenin (15); three benzenoids, i.e., 4-hydroxybenzaldehyde (16), vanillin (17), and (S)-lasiodiplodin (18); five steroids, i.e., ergosterol peroxide (19), a mixture of 6beta-Hydroxystigmast-4-en-3-one (20) and 6beta-hydroxystigmasta-4,22-dien-3-one (21), and a mixture of beta-sitosterol (22) and stigmasterol (23); and one triterpenoid, i.e., oleanolic acid (24) from the roots of Ficus nervosa. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR as well as MS analyses. Among these isolates, 3-hydroxyxanthyletin (1), genistein (10), prunetin (12), and (2S)-naringenin (15) showed antimycobacterial activities against Mycobacterium tuberculosis H(37)R(V) in vitro with MIC values of 16, 35, 30, and < or =2.8 microg/ml, respectively.

Triterpenoids from the roots of Pterospermum heterophyllum Hance.[Pubmed:20183302]

J Asian Nat Prod Res. 2009 Jul;11(7):652-7.

Two new triterpenoids taraxer-14-ene-1alpha,3beta-diol (1) and 3beta-hydroxytaraxer-14-ene-1-one (2), together with the known triterpenes taraxerol (3), betulin (4), betulinic acid (5), sumaresinolic acid (6), and 5-hydroxy-2-methoxy-1,4-naphthoquinone (7), 5,7-dihydroxy-6,8-dimethylchromone (8), alpha-monpalmitin (9), palmitic acid (10), 6beta-Hydroxystigmast-4-en-3-one (11), beta-sitostero1 (12), have been isolated from the petroleum ether fraction of the ethanolic extract of Pterospermum heterophyllum. Their structures were established by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds 1-8 were evaluated against several human cancer cell lines. Compound 1 showed in vitro selective cytotoxicity against human lung cancer cell lines (A549) with an IC(50) value of 1.22 microM. Compound 7 showed significant cytotoxicity against the A549, HCT-8, Bel7402, BGC-823, and A2780 cancer cell lines with IC(50) values of 0.21, 0.55, 0.40, 0.59, and 0.34 microM, respectively. However, the other compounds were inactive (IC(50)>10 microM).

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