MedKoo Cat#: 598602 | Name: Leptocarpin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Leptocarpin is a plant-derived sesquiterpene lactone isolated from Leptocarpha rivularis.

Chemical Structure

Leptocarpin
Leptocarpin
CAS#73522-63-1 (free base)

Theoretical Analysis

MedKoo Cat#: 598602

Name: Leptocarpin

CAS#: 73522-63-1 (free base)

Chemical Formula: C20H26O6

Exact Mass: 362.1729

Molecular Weight: 362.42

Elemental Analysis: C, 66.28; H, 7.23; O, 26.49

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Leptocarpin;
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
Appearance
Solid powder
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
More Info

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.

Recalculate based on batch purity %
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.