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Trachelanthamine

CAS# 14140-18-2

Trachelanthamine

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Chemical structure

Trachelanthamine

3D structure

Chemical Properties of Trachelanthamine

Cas No. 14140-18-2 SDF Download SDF
PubChem ID 26477 Appearance Cryst.
Formula C15H27NO4 M.Wt 285.38
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1S,8S)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (2R)-2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
SMILES CC(C)C(C(C)O)(C(=O)OCC1CCN2C1CCC2)O
Standard InChIKey BWQSLRZZOVFVHJ-VYHDIPPYSA-N
Standard InChI InChI=1S/C15H27NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h10-13,17,19H,4-9H2,1-3H3/t11?,12-,13+,15-/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.

Biological Activity of Trachelanthamine

DescriptionTrachelanthamine is a natural product from Eupatorium fortunei.

Protocol of Trachelanthamine

Structure Identification
Phytochemistry, 2007,68(7):1026-37.

Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species.[Pubmed: 17320124]


METHODS AND RESULTS:
Classical tracer studies with radioactively labelled precursor amines (e.g., putrescine, spermidine and homospermidine) and various necine bases (trachelanthamidine, supinidine, retronecine, heliotridine) and potential ester alkaloid intermediates (e.g., Trachelanthamine, supinine) were performed to evaluate the biosynthetic sequences.

Trachelanthamine Dilution Calculator

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Trachelanthamine Molarity Calculator

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Preparing Stock Solutions of Trachelanthamine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5041 mL 17.5205 mL 35.041 mL 70.082 mL 87.6025 mL
5 mM 0.7008 mL 3.5041 mL 7.0082 mL 14.0164 mL 17.5205 mL
10 mM 0.3504 mL 1.752 mL 3.5041 mL 7.0082 mL 8.7602 mL
50 mM 0.0701 mL 0.3504 mL 0.7008 mL 1.4016 mL 1.752 mL
100 mM 0.035 mL 0.1752 mL 0.3504 mL 0.7008 mL 0.876 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 Trachelanthamine

Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species.[Pubmed:17320124]

Phytochemistry. 2007 Apr;68(7):1026-37.

Three species of the Boraginaceae were studied: greenhouse-grown plants of Heliotropium indicum and Agrobacterium rhizogenes transformed roots cultures (hairy roots) of Cynoglossum officinale and Symphytum officinale. The species-specific pyrrolizidine alkaloid (PA) profiles of the three systems were established by GC-MS. All PAs are genuinely present as N-oxides. In H. indicum the tissue-specific PA distribution revealed the presence of PAs in all tissues with the highest levels in the inflorescences which in a flowering plant may account for more than 70% of total plant alkaloid. The sites of PA biosynthesis vary among species. In H. indicum PAs are synthesized in the shoot but not roots whereas they are only made in shoots for C. officinale and in roots of S. officinale. Classical tracer studies with radioactively labelled precursor amines (e.g., putrescine, spermidine and homospermidine) and various necine bases (trachelanthamidine, supinidine, retronecine, heliotridine) and potential ester alkaloid intermediates (e.g., Trachelanthamine, supinine) were performed to evaluate the biosynthetic sequences. It was relevant to perform these comparative studies since the key enzyme of the core pathway, homospermidine synthase, evolved independently in the Boraginaceae and, for instance, in the Asteraceae [Reimann, A., Nurhayati, N., Backenkohler, A., Ober, D., 2004. Repeated evolution of the pyrrolizidine alkaloid-mediated defense system in separate angiosperm lineages. Plant Cell 16, 2772-2784.]. These studies showed that the core pathway for the formation of trachelanthamidine from putrescine and spermidine via homospermidine is common to the pathway in Senecio ssp. (Asteraceae). In both pathways homospermidine is further processed by a beta-hydroxyethylhydrazine sensitive diamine oxidase. Further steps of PA biosynthesis starting with trachelanthamidine as common precursor occur in two successive stages. Firstly, the necine bases are structurally modified and either before or after this modification are converted into their O(9)-esters by esterification with one of the stereoisomers of 2,3-dihydroxy-2-isopropylbutyric acid, the unique necic acid of PAs of the lycopsamine type. Secondly, the necine O(9)-esters may be further diversified by O(7)- and/or O(3')-acylation.

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