Synonym
Jatrophatrione; NSC 254668; NSC-254668; NSC254668;
IUPAC/Chemical Name
(3aR,9R,10aS,11aS,Z)-3,3,6,9,11a-pentamethyl-2,3,3a,10,10a,11a-hexahydro-1H-dicyclopenta[a,d][9]annulene-1,5,11(4H,9H)-trione
InChi Key
TYBGBKQPLBAYQG-CJIMKZOCSA-N
InChi Code
InChI=1S/C20H26O3/c1-11-6-13-8-12(2)15(21)9-16-19(3,4)10-17(22)20(16,5)18(23)14(13)7-11/h6,8,11,14,16H,7,9-10H2,1-5H3/b12-8-/t11-,14-,16+,20-/m0/s1
SMILES Code
O=C1CC(C)(C)[C@]2([H])[C@]1(C)C([C@]3([H])C(/C=C(C)\C(C2)=O)=C[C@H](C)C3)=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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
314.42
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: Melchor-Martínez EM, Silva-Mares DA, Torres-López E, Waksman-Minsky N, Pauli GF, Chen SN, Niemitz M, Sánchez-Castellanos M, Toscano A, Cuevas G, Rivas-Galindo VM. Stereochemistry of a Second Riolozane and Other Diterpenoids from Jatropha dioica. J Nat Prod. 2017 Aug 25;80(8):2252-2262. doi: 10.1021/acs.jnatprod.7b00193. Epub 2017 Aug 3. PubMed PMID: 28771358; PubMed Central PMCID: PMC5714812.
2: Yang J, Long YO, Paquette LA. Concise total syntheses of the bioactive mesotricyclic diterpenoids jatrophatrione and citlalitrione. J Am Chem Soc. 2003 Feb 12;125(6):1567-74. PubMed PMID: 12568617.
3: Paquette LA, Yang J, Long YO. Concerning the antileukemic agent jatrophatrione: the first total synthesis of a [5.9.5] tricyclic diterpene. J Am Chem Soc. 2002 Jun 12;124(23):6542-3. PubMed PMID: 12047168.
4: Paquette LA, Edmondson SD, Monck N, Rogers RD. Studies Directed toward the Synthesis of the Unusual Antileukemic Diterpene Jatrophatrione. 2. Functionalization of Advanced Polycyclic Precursors to the 9-Epi and 8,9-Dehydro Congeners. J Org Chem. 1999 Apr 30;64(9):3255-3265. PubMed PMID: 11674428.
5: Paquette LA, Nakatani S, Zydowsky TM, Edmondson SD, Sun LQ, Skerlj R. Studies Directed toward the Synthesis of the Unusual Antileukemic Diterpene Jatrophatrione. 1. A Solution to the Problem of Chirality Merger during Elaboration of the Entire Carbotricyclic Framework. J Org Chem. 1999 Apr 30;64(9):3244-3254. PubMed PMID: 11674427.
6: Torrance SJ, Wiedhopf RM, Cole JR, Arora SK, Bates RB, Beavers WA, Cutler RS. Antitumor agents from Jatropha macrorhiza (Euphorbiaceae). II. Isolation and characterization of jatrophatrione. J Org Chem. 1976 May 14;41(10):1855-7. PubMed PMID: 1262992.
