IUPAC/Chemical Name
(3S,3aR,4S,5S,6R,7aS)-6-((4S,5R,5aR,9aR)-4-acetoxy-5,9a-dimethyl-2,7-dioxooctahydro-2H-pyrano[3,4-b]oxepin-5-yl)-5-(formyloxy)-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylene-1-oxooctahydro-1H-inden-4-yl 3-methylbutanoate
InChi Key
BGIQNWKPRGQOMD-QRUKZMRSSA-N
InChi Code
InChI=1S/C34H42O13/c1-17(2)10-26(39)46-30-29(44-16-35)28(18(3)34(41)23(37)11-21(33(30,34)7)20-8-9-42-14-20)32(6)22-12-25(38)43-15-31(22,5)47-27(40)13-24(32)45-19(4)36/h8-9,14,16-17,21-22,24,28-30,41H,3,10-13,15H2,1-2,4-7H3/t21-,22-,24-,28+,29-,30+,31-,32+,33+,34+/m0/s1
SMILES Code
CC(C)CC(O[C@H]([C@@H](OC=O)[C@H]([C@]([C@@H](OC(C)=O)C1)(C)[C@]2([H])[C@@](COC(C2)=O)(C)OC1=O)C([C@@]34O)=C)[C@@]4(C)[C@H](C5=COC=C5)CC3=O)=O
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
658.69
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: Sarker SD, Savchenko T, Whiting P, Sik V, Dinan L. Two limonoids from Turraea obtusifolia (Meliaceae), prieurianin and rohitukin, antagonise 20-hydroxyecdysone action in a Drosophila cell line. Arch Insect Biochem Physiol. 1997;35(1-2):211-7. PubMed PMID: 9131785.
2: Dzoyem JP, Tsamo AT, Melong R, Mkounga P, Nkengfack AE, McGaw LJ, Eloff JN. Cytotoxicity, nitric oxide and acetylcholinesterase inhibitory activity of three limonoids isolated from Trichilia welwitschii (Meliaceae). Biol Res. 2015 Oct 13;48:57. doi: 10.1186/s40659-015-0049-0. PubMed PMID: 26463660; PubMed Central PMCID: PMC4604621.
3: Mohanakumara P, Sreejayan N, Priti V, Ramesha BT, Ravikanth G, Ganeshaiah KN, Vasudeva R, Mohan J, Santhoshkumar TR, Mishra PD, Ram V, Shaanker RU. Dysoxylum binectariferum Hook.f (Meliaceae), a rich source of rohitukine. Fitoterapia. 2010 Mar;81(2):145-8. doi: 10.1016/j.fitote.2009.08.010. Epub 2009 Aug 15. PubMed PMID: 19686817.
4: Polonsky J, Varon Z, Marazano C, Arnoux B, Pettit GR, Schmid JM, Ochi M, Kotsuki H. The structure of amoorastatone and the cytotoxic limonoid 12-hydroxyamoorastatin. Experientia. 1979 Aug 15;35(8):987-9. PubMed PMID: 477905.
5: Keshri G, Oberoi RM, Lakshmi V, Pandey K, Singh MM. Contraceptive and hormonal properties of the stem bark of Dysoxylum binectariferum in rat and docking analysis of rohitukine, the alkaloid isolated from active chloroform soluble fraction. Contraception. 2007 Nov;76(5):400-7. Epub 2007 Oct 4. PubMed PMID: 17963866.
