Tropinone

CAS# 532-24-1

Tropinone

Catalog No. BCN1935----Order now to get a substantial discount!

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Quality Control of Tropinone

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Chemical structure

Tropinone

3D structure

Chemical Properties of Tropinone

Cas No. 532-24-1 SDF Download SDF
PubChem ID 79038 Appearance White to yellowish solid
Formula C8H13NO M.Wt 139.19
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 8-methyl-8-azabicyclo[3.2.1]octan-3-one
SMILES CN1C2CCC1CC(=O)C2
Standard InChIKey QQXLDOJGLXJCSE-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H13NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-7H,2-5H2,1H3
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 Tropinone

The roots of Atropa belladonna

Biological Activity of Tropinone

DescriptionTropinone is a decane alkaloid, used as an intermediate in the synthesis of atropine sulfate.
In vitro

Substrate flexibility and reaction specificity of tropinone reductase-like short-chain dehydrogenases.[Pubmed: 24583623]

Bioorg Chem. 2014 Apr;53:37-49.

Annotations of protein or gene sequences from large scale sequencing projects are based on protein size, characteristic binding motifs, and conserved catalytic amino acids, but biochemical functions are often uncertain.
METHODS AND RESULTS:
In the large family of short-chain dehydrogenases/reductases (SDRs), functional predictions often fail. Putative Tropinone reductases, named Tropinone reductase-like (TRL), are SDRs annotated in many genomes of organisms that do not contain tropane alkaloids. SDRs in vitro often accept several substrates complicating functional assignments. Cochlearia officinalis, a Brassicaceae, contains tropane alkaloids, in contrast to the closely related Arabidopsis thaliana. TRLs from Arabidopsis and the Tropinone reductase isolated from Cochlearia (CoTR) were investigated for their catalytic capacity. In contrast to CoTR, none of the Arabidopsis TRLs reduced Tropinone in vitro. NAD(H) and NADP(H) preferences were relaxed in two TRLs, and protein homology models revealed flexibility of amino acid residues in the active site allowing binding of both cofactors. TRLs reduced various carbonyl compounds, among them terpene ketones. The reduction was stereospecific for most of TRLs investigated, and the corresponding terpene alcohol oxidation was stereoselective. Carbonyl compounds that were identified to serve as substrates were applied for modeling pharmacophores of each TRL. A database of commercially available compounds was screened using the pharmacophores. Compounds identified as potential substrates were confirmed by turnover in vitro.
CONCLUSIONS:
Thus pharmacophores may contribute to better predictability of biochemical functions of SDR enzymes.

Protocol of Tropinone

Structure Identification
J Org Chem. 2014 Dec 5;79(23):11609-18.

A twist on facial selectivity of hydride reductions of cyclic ketones: twist-boat conformers in cyclohexanone, piperidone, and tropinone reactions.[Pubmed: 25372509]

The role of twist-boat conformers of cyclohexanones in hydride reductions was explored.
METHODS AND RESULTS:
The hydride reductions of a cis-2,6-disubstituted N-acylpiperidone, an N-acylTropinone, and tert-butylcyclohexanone by lithium aluminum hydride and by a bulky borohydride reagent were investigated computationally and compared to experiment. Our results indicate that in certain cases, factors such as substrate conformation, nucleophile bulkiness, and remote steric features can affect stereoselectivity in ways that are difficult to predict by the general Felkin-Anh model. In particular, we have calculated that a twist-boat conformation is relevant to the reactivity and facial selectivity of hydride reduction of cis-2,6-disubstituted N-acylpiperidones with a small hydride reagent (LiAlH4) but not with a bulky hydride (lithium triisopropylborohydride).

Chem Commun (Camb). 2013 Nov 28;49(92):10775-7.

Robinson's landmark synthesis of tropinone.[Pubmed: 24116374]

The 1917 total synthesis of Tropinone by Sir Robert Robinson represents a landmark achievement in organic synthesis. Decades ahead of its time in terms of its retrosynthetic logic and biomimetic approach, the elegant combination of these two elements in this synthesis continues to serve as an inspiration for the development of new and efficient strategies for complex molecule synthesis.

Tropinone Dilution Calculator

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Tropinone Molarity Calculator

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Preparing Stock Solutions of Tropinone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 7.1844 mL 35.9221 mL 71.8442 mL 143.6885 mL 179.6106 mL
5 mM 1.4369 mL 7.1844 mL 14.3688 mL 28.7377 mL 35.9221 mL
10 mM 0.7184 mL 3.5922 mL 7.1844 mL 14.3688 mL 17.9611 mL
50 mM 0.1437 mL 0.7184 mL 1.4369 mL 2.8738 mL 3.5922 mL
100 mM 0.0718 mL 0.3592 mL 0.7184 mL 1.4369 mL 1.7961 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 Tropinone

Robinson's landmark synthesis of tropinone.[Pubmed:24116374]

Chem Commun (Camb). 2013 Nov 28;49(92):10775-7.

The 1917 total synthesis of Tropinone by Sir Robert Robinson represents a landmark achievement in organic synthesis. Decades ahead of its time in terms of its retrosynthetic logic and biomimetic approach, the elegant combination of these two elements in this synthesis continues to serve as an inspiration for the development of new and efficient strategies for complex molecule synthesis.

A twist on facial selectivity of hydride reductions of cyclic ketones: twist-boat conformers in cyclohexanone, piperidone, and tropinone reactions.[Pubmed:25372509]

J Org Chem. 2014 Dec 5;79(23):11609-18.

The role of twist-boat conformers of cyclohexanones in hydride reductions was explored. The hydride reductions of a cis-2,6-disubstituted N-acylpiperidone, an N-acylTropinone, and tert-butylcyclohexanone by lithium aluminum hydride and by a bulky borohydride reagent were investigated computationally and compared to experiment. Our results indicate that in certain cases, factors such as substrate conformation, nucleophile bulkiness, and remote steric features can affect stereoselectivity in ways that are difficult to predict by the general Felkin-Anh model. In particular, we have calculated that a twist-boat conformation is relevant to the reactivity and facial selectivity of hydride reduction of cis-2,6-disubstituted N-acylpiperidones with a small hydride reagent (LiAlH4) but not with a bulky hydride (lithium triisopropylborohydride).

Substrate flexibility and reaction specificity of tropinone reductase-like short-chain dehydrogenases.[Pubmed:24583623]

Bioorg Chem. 2014 Apr;53:37-49.

Annotations of protein or gene sequences from large scale sequencing projects are based on protein size, characteristic binding motifs, and conserved catalytic amino acids, but biochemical functions are often uncertain. In the large family of short-chain dehydrogenases/reductases (SDRs), functional predictions often fail. Putative Tropinone reductases, named Tropinone reductase-like (TRL), are SDRs annotated in many genomes of organisms that do not contain tropane alkaloids. SDRs in vitro often accept several substrates complicating functional assignments. Cochlearia officinalis, a Brassicaceae, contains tropane alkaloids, in contrast to the closely related Arabidopsis thaliana. TRLs from Arabidopsis and the Tropinone reductase isolated from Cochlearia (CoTR) were investigated for their catalytic capacity. In contrast to CoTR, none of the Arabidopsis TRLs reduced Tropinone in vitro. NAD(H) and NADP(H) preferences were relaxed in two TRLs, and protein homology models revealed flexibility of amino acid residues in the active site allowing binding of both cofactors. TRLs reduced various carbonyl compounds, among them terpene ketones. The reduction was stereospecific for most of TRLs investigated, and the corresponding terpene alcohol oxidation was stereoselective. Carbonyl compounds that were identified to serve as substrates were applied for modeling pharmacophores of each TRL. A database of commercially available compounds was screened using the pharmacophores. Compounds identified as potential substrates were confirmed by turnover in vitro. Thus pharmacophores may contribute to better predictability of biochemical functions of SDR enzymes.

Description

Tropinone, an alkaloid, acts as a synthetic intermediate to Atropine.

Keywords:

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