Himandridine
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| Category | Others |
| Catalog number | BBF-04728 |
| CAS | 15521-76-3 |
| Molecular Weight | 523.62 |
| Molecular Formula | C30H37NO7 |
| Purity | >95% by HPLC |
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Description
Himandridine is a piperidine alkaloid isolated from Galbulimia sp.
Specification
| Storage | Store at -20°C |
| IUPAC Name | methyl 14-benzoyloxy-11,17-dihydroxy-16-methoxy-3-methyl-2-azahexacyclo[10.8.0.01,9.02,7.06,11.015,20]icos-12-ene-13-carboxylate |
| Canonical SMILES | CC1CCC2C3N1C45C6CCC(C(C6C(C(=C4C2(CC5C3)O)C(=O)OC)OC(=O)C7=CC=CC=C7)OC)O |
| InChI | InChI=1S/C30H37NO7/c1-15-9-10-18-20-13-17-14-29(18,35)26-23(28(34)37-3)25(38-27(33)16-7-5-4-6-8-16)22-19(30(17,26)31(15)20)11-12-21(32)24(22)36-2/h4-8,15,17-22,24-25,32,35H,9-14H2,1-3H3 |
| InChI Key | QERMOAWMXXPSEU-UHFFFAOYSA-N |
Properties
| Boiling Point | 673°C at 760 mmHg |
| Density | 1.37 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Progress toward the syntheses of (+)-GB 13, (+)-himgaline, and himandridine. new insights into intramolecular imine/enamine aldol cyclizations
David A Evans, Drew J Adams, Eugene E Kwan J Am Chem Soc. 2012 May 16;134(19):8162-70. doi: 10.1021/ja3001776. Epub 2012 May 3.
A full account of our total synthesis of the galbulimima alkaloids GB 13 and himgaline is provided. Using a strategy adapted from the proposed biosynthesis of the GB alkaloid family, a linear precursor underwent successive intramolecular Diels-Alder, Michael, and imine aldol cyclizations to form the polycyclic alkaloid core. We now show that modification of this strategy can also deliver an advanced intermediate en route to the related alkaloid himandridine. The success of the key imine aldol cyclization is acutely sensitive to substrate structure and solvent, including a case in which cyclization was spontaneous in protic solvents. A detailed computational investigation of the course of the reaction closely correlates with, and suggests a rationale for, the observed patterns of imine aldol reactivity.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
