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509-15-9,MFCD00082347
Catalog No.:AA00DA2B

509-15-9 | Gelsemine

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5mg
98% by HPLC
in stock  
$224.00   $157.00
- +
10mg
98% by HPLC
in stock  
$335.00   $234.00
- +
25mg
98% by HPLC
in stock  
$637.00   $446.00
- +
50mg
98% by HPLC
in stock  
$1,040.00   $728.00
- +
100mg
98% by HPLC
in stock  
$1,752.00   $1,227.00
- +
500mg
98% by HPLC
in stock  
$5,515.00   $3,861.00
- +
1000mg
98% by HPLC
in stock  
$8,787.00   $6,151.00
- +
  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DA2B
Chemical Name:
Gelsemine
CAS Number:
509-15-9
Molecular Formula:
C20H22N2O2
Molecular Weight:
322.4009
MDL Number:
MFCD00082347
SMILES:
C=CC12CN([C@H]3[C@@H]2[C@]2([C@H]4C[C@@H]1C3CO4)C(=O)Nc1c2cccc1)C
Properties
Computed Properties
 
Complexity:
635  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
1.8  

Literature

Title: Biomimetic total synthesis of (+)-gelsemine.

Journal: Angewandte Chemie (International ed. in English) 20120514

Title: Nectar alkaloids decrease pollination and female reproduction in a native plant.

Journal: Oecologia 20120401

Title: [Study on anti-proliferation activity and the mechanisms of alkaloid monomers from Gelsemium elegans on HepG2 cell in vitro].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120301

Title: Preparative separation of alkaloids from Gelsemium elegans Benth. using pH-zone-refining counter-current chromatography.

Journal: Journal of chromatography. A 20110610

Title: Antitumor activity of two gelsemine metabolites in rat liver microsomes.

Journal: Journal of Asian natural products research 20100901

Title: A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy.

Journal: Organic letters 20081106

Title: Regulation of neurosteroid allopregnanolone biosynthesis in the rat spinal cord by glycine and the alkaloidal analogs strychnine and gelsemine.

Journal: Neuroscience 20080422

Title: Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.

Journal: Organic letters 20070802

Title: Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.

Journal: The Journal of organic chemistry 20070608

Title: Isolation of gelsedine-type indole alkaloids from Gelsemium elegans and evaluation of the cytotoxic activity of gelsemium alkaloids for A431 epidermoid carcinoma cells.

Journal: Journal of natural products 20060401

Title: Aza-cope rearrangement-mannich cyclizations for the formation of complex tricyclic amines: stereocontrolled total synthesis of (+/-)-gelsemine.

Journal: Journal of the American Chemical Society 20051228

Title: Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.

Journal: Journal of the American Chemical Society 20051228

Title: Modeling the stereoselectivity of the Johnson-Claisen rearrangements in the Danishefsky synthesis of gelsemine.

Journal: The Journal of organic chemistry 20050902

Title: A convenient one-pot procedure to afford bicyclic molecules by stereospecific iron carbonyl mediated [6 + 2] ene-type cyclization: a possible approach to gelsemine.

Journal: Journal of the American Chemical Society 20031105

Title: Gelsemine: a thought-provoking target for total synthesis.

Journal: Angewandte Chemie (International ed. in English) 20030103

Title: Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemine.

Journal: Journal of the American Chemical Society 20020821

Title: Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products.

Journal: Chemical record (New York, N.Y.) 20020101

Title: Wu YE, et al. Gelsemine alleviates both neuropathic pain and sleep disturbance in partial sciatic nerve ligation mice. Acta Pharmacol Sin. 2015 Nov;36(11):1308-17.

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