Tropinone | CAS:532-24-1 | Manufacturer ChemFaces

Tropinone

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Description:

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

In vitro:

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

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

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.

Tropinone Description

Source:	The roots of Atropa belladonna
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

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.

Product Name	Tropinone
Price:	$30 / 20mg
CAS No.:	532-24-1
Catalog No.:	CFN00220
Molecular Formula:	C₈H₁₃NO
Molecular Weight:	139.19 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	The roots of Atropa belladonna
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Alkaloids Compound Library

	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

CFN00205	Tropine	120-29-6	141.21	C₈H₁₅NO
CFN00206	Tropine acetate	3423-27-6	183.25	C₁₀H₁₇NO₂
CFN00207	Tropine isobutyrate	495-80-7	211.30	C₁₂H₂₁NO₂
CFN00209	Tropine nonanoate	146018-90-8	281.44	C₁₇H₃₁NO₂
CFN00217	Pseudotropine	135-97-7	141.21	C₈H₁₅NO
CFN00218	3-Acetoxytropane	3423-26-5	183.25	C₁₀H₁₇NO₂
CFN00220	Tropinone	532-24-1	139.19	C₈H₁₃NO
CFN00477	6-Hydroxytropinone	5932-53-6	155.2	C₈H₁₃NO₂
CFN00221	Physoperuvine	60723-27-5	141.21	C₈H₁₅NO
CFN00226	Scopine	498-45-3	155.20	C₈H₁₃NO₂