IUPAC/Chemical Name
(1aS,3R,5aR,8aR,9R,10aR,E)-3-hydroxy-4,10a-dimethyl-8-methylene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[2',3':5,6]cyclodeca[1,2-b]furan-9-yl (Z)-2-methylbut-2-enoate
InChi Key
DZTWAOVNNLDWNH-GPRDXGMASA-N
InChi Code
InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6-,11-7+/t13-,14-,15-,16+,17+,20-/m1/s1
SMILES Code
O[C@@H]1C[C@H](O2)[C@@]2(C)C[C@@H](OC(/C(C)=C\C)=O)[C@@H](C(C(O3)=O)=C)[C@H]3/C=C1\C
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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
362.42
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: Bosio C, Tomasoni G, Martínez R, Olea AF, Carrasco H, Villena J. Cytotoxic and apoptotic effects of leptocarpin, a plant-derived sesquiterpene lactone, on human cancer cell lines. Chem Biol Interact. 2015 Dec 5;242:415-21. doi: 10.1016/j.cbi.2015.11.006. Epub 2015 Nov 10. PubMed PMID: 26562779.
2: Martínez R, Kesternich V, Gutierrez E, Dölz H, Mansilla H. Conformational analysis and biological activity of leptocarpin and leptocarpin acetate. Planta Med. 1995 Apr;61(2):188-9. PubMed PMID: 7753932.
3: El Marsni Z, Torres A, Varela RM, Molinillo JM, Casas L, Mantell C, Martinez de la Ossa EJ, Macias FA. Isolation of Bioactive Compounds from Sunflower Leaves (Helianthus annuus L.) Extracted with Supercritical Carbon Dioxide. J Agric Food Chem. 2015 Jul 22;63(28):6410-21. doi: 10.1021/acs.jafc.5b02261. Epub 2015 Jul 7. PubMed PMID: 26151222.
4: Macías FA, Torres A, Galindo JL, Varela RM, Alvarez JA, Molinillo JM. Bioactive terpenoids from sunflower leaves cv. Peredovick. Phytochemistry. 2002 Nov;61(6):687-92. PubMed PMID: 12423890.
5: Zheng SW, Wan WG, Miao HX, Tang R, Wang B, Huang QZ, Liu WL, Zheng JP, Chen CQ, Zhong HB, Li SF, Sun CH. Leptocarpin Suppresses Proliferation, Migration, and Invasion of Human Osteosarcoma by Targeting Type-1 Insulin-Like Growth Factor Receptor (IGF-1R). Med Sci Monit. 2017 Aug 27;23:4132-4140. PubMed PMID: 28844074; PubMed Central PMCID: PMC5584868.