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6-Angeloyloxyditropan-3-yl itaconate

CAS# 182015-05-0

6-Angeloyloxyditropan-3-yl itaconate

2D Structure

Catalog No. BCN1867----Order now to get a substantial discount!

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6-Angeloyloxyditropan-3-yl itaconate: 5mg Please Inquire In Stock
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Quality Control of 6-Angeloyloxyditropan-3-yl itaconate

3D structure

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6-Angeloyloxyditropan-3-yl itaconate

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Chemical Properties of 6-Angeloyloxyditropan-3-yl itaconate

Cas No. 182015-05-0 SDF Download SDF
PubChem ID 134715039 Appearance Oil
Formula C26H38N2O6 M.Wt 474.60
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-O-[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 4-O-[(1R,3R,5S,6R)-8-methyl-6-[(Z)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] 2-methylidenebutanedioate
SMILES CC=C(C)C(=O)OC1CC2CC(CC1N2C)OC(=O)CC(=C)C(=O)OC3CC4CCC(C3)N4C
Standard InChIKey VWKHLWKXXWUJID-WGSXQKLXSA-N
Standard InChI InChI=1S/C26H38N2O6/c1-6-15(2)25(30)34-23-13-19-12-21(14-22(23)28(19)5)32-24(29)9-16(3)26(31)33-20-10-17-7-8-18(11-20)27(17)4/h6,17-23H,3,7-14H2,1-2,4-5H3/b15-6-/t17-,18+,19-,20?,21-,22+,23-/m1/s1
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.

6-Angeloyloxyditropan-3-yl itaconate Dilution Calculator

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6-Angeloyloxyditropan-3-yl itaconate Molarity Calculator

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Preparing Stock Solutions of 6-Angeloyloxyditropan-3-yl itaconate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.107 mL 10.5352 mL 21.0704 mL 42.1408 mL 52.6759 mL
5 mM 0.4214 mL 2.107 mL 4.2141 mL 8.4282 mL 10.5352 mL
10 mM 0.2107 mL 1.0535 mL 2.107 mL 4.2141 mL 5.2676 mL
50 mM 0.0421 mL 0.2107 mL 0.4214 mL 0.8428 mL 1.0535 mL
100 mM 0.0211 mL 0.1054 mL 0.2107 mL 0.4214 mL 0.5268 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 6-Angeloyloxyditropan-3-yl itaconate

Draft Genome Sequences of Itaconate-Producing Ustilaginaceae.[Pubmed:27979931]

Genome Announc. 2016 Dec 15;4(6). pii: 4/6/e01291-16.

Some smut fungi of the family Ustilaginaceae produce itaconate from glucose. De novo genome sequencing of nine itaconate-producing Ustilaginaceae revealed genome sizes between 19 and 25 Mbp. Comparison to the itaconate cluster of U. maydis MB215 revealed all essential genes for itaconate production contributing to metabolic engineering for improving itaconate production.

Dimethyl Itaconate Is Not Metabolized into Itaconate Intracellularly.[Pubmed:28188288]

J Biol Chem. 2017 Mar 24;292(12):4766-4769.

Itaconic acid is an important metabolite produced by macrophages after stimulation with LPS. The role of itaconate in the inflammatory cascade is unclear. Here we used [(13)C]itaconate and dimethyl [(13)C]itaconate (DMI) to probe itaconate metabolism, and find that [(13)C]DMI is not metabolized to itaconate. [(13)C]Itaconate in the cell culture medium leads to elevated intracellular levels of unlabeled succinate, with no evidence of intracellular uptake. The goal of this study is to encourage the development of effective pro-drug strategies to increase the intracellular levels of itaconate, which will enable more conclusive analysis of its action on macrophages and other cell and tissue types.

Genetic and biochemical insights into the itaconate pathway of Ustilago maydis enable enhanced production.[Pubmed:27750034]

Metab Eng. 2016 Nov;38:427-435.

The Ustilaginaceae family of smut fungi, especially Ustilago maydis, gained biotechnological interest over the last years, amongst others due to its ability to naturally produce the versatile bio-based building block itaconate. Along with itaconate, U. maydis also produces 2-hydroxyparaconate. The latter was proposed to be derived from itaconate, but the underlying biochemistry and associated genes were thus far unknown. Here, we confirm that 2-hydroxyparaconate is a secondary metabolite of U. maydis and propose an extension of U. maydis' itaconate pathway from itaconate to 2-hydroxyparaconate. This conversion is catalyzed by the P450 monooxygenase Cyp3, encoded by cyp3, a gene, which is adjacent to the itaconate gene cluster of U. maydis. By deletion of cyp3 and simultaneous overexpression of the gene cluster regulator ria1, it was possible to generate an itaconate hyper producer strain, which produced up to 4.5-fold more itaconate in comparison to the wildtype without the by-product 2-hydroxyparaconate. By adjusting culture conditions in controlled pulsed fed-batch fermentations, a product to substrate yield of 67% of the theoretical maximum was achieved. In all, the titer, rate and yield of itaconate produced by U. maydis was considerably increased, thus contributing to the industrial application of this unicellular fungus for the biotechnological production of this valuable biomass derived chemical.

Production of itaconate by whole-cell bioconversion of citrate mediated by expression of multiple cis-aconitate decarboxylase (cadA) genes in Escherichia coli.[Pubmed:28051098]

Sci Rep. 2017 Jan 4;7:39768.

Itaconate, a C5 unsaturated dicarboxylic acid, is an important chemical building block that is used in manufacturing high-value products, such as latex and superabsorbent polymers. Itaconate is produced by fermentation of sugars by the filamentous fungus Aspergillus terreus. However, fermentation by A. terreus involves a long fermentation period and the formation of various byproducts, resulting in high production costs. E. coli has been developed as an alternative for producing itaconate. However, fermentation of glucose gives low conversion yields and low productivity. Here, we report the whole-cell bioconversion of citrate to itaconate with enhanced aconitase and cis-aconitate decarboxylase activities by controlling the expression of multiple cadA genes. In addition, this bioconversion system does not require the use of buffers, which reduces the production cost and the byproducts released during purification. Using this whole-cell bioconversion system, we were able to catalyze the conversion of 319.8 mM of itaconate (41.6 g/L) from 500 mM citrate without any buffer system or additional cofactors, with 64.0% conversion in 19 h and a productivity of 2.19 g/L/h. Our bioconversion system suggests very high productivity for itaconate production.

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