IUPAC/Chemical Name
Zephyranthine.
InChi Key
VJILFEGOWCJNIK-MGRBZGILSA-N
InChi Code
InChI=1S/C16H19NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h4-5,8,11,14-16,18-19H,1-3,6-7H2/t8-,11+,14+,15-,16-/m1/s1
SMILES Code
c1c2C[N@@]3CC[C@H]4[C@@H]3[C@H](c2cc2c1OCO2)[C@H](O)[C@@H](O)C4
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
289.33
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Chen YJ, Cai SL, Wang CC, Cheng JD, Kramer S, Sun XW. Asymmetric Total Syntheses of (-)-α-Lycorane, (-)-Zephyranthine, and Formal Synthesis of (+)-Clivonine. Chem Asian J. 2017 Jun 19;12(12):1309-1313. doi: 10.1002/asia.201700555. Epub 2017 May 31. PubMed PMID: 28474489.
2: Padwa A, Wang Q. Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans. J Org Chem. 2006 Sep 15;71(19):7391-402. PubMed PMID: 16958534; PubMed Central PMCID: PMC2494947.
3: Wang Q, Padwa A. Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine. Org Lett. 2004 Jun 24;6(13):2189-92. PubMed PMID: 15200317.
4: Herrera MR, Machocho AK, Nair JJ, Campbell WE, Brun R, Viladomat F, Codina C, Bastida J. Alkaloids from Cyrtanthus elatus. Fitoterapia. 2001 May;72(4):444-8. PubMed PMID: 11395276.
5: OZEKI S. [STUDIES ON THE ALKALOIDS OF ZEPHYRANTHES CANDIDA HERB. II. STRUCTURE OF ZEPHYRANTHINE]. Yakugaku Zasshi. 1965 Mar;85:200-5. Japanese. PubMed PMID: 14322082.
6: OZEKI S. STRUCTURE OF ZEPHYRANTHINE, A NEW ALKALOID ISOLATED FROM ZEPHYRANTHES CANDIDA HERB. Chem Pharm Bull (Tokyo). 1964 Feb;12:253-4. PubMed PMID: 14126758.
