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MedKoo Cat#: 527961 | Name: Luffariellolide

Description:

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

Luffariellolide is a partially reversible phospholipase A2 inhibitor; a major metabolite of the sponge Luffariella.

Chemical Structure

Luffariellolide
Luffariellolide
CAS#111149-87-2

Theoretical Analysis

MedKoo Cat#: 527961

Name: Luffariellolide

CAS#: 111149-87-2

Chemical Formula: C25H38O3

Exact Mass: 386.2821

Molecular Weight: 386.58

Elemental Analysis: C, 77.68; H, 9.91; O, 12.42

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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Related CAS #
No Data
Synonym
Luffariellolide
IUPAC/Chemical Name
2(5H)-Furanone, 4-(4,8-dimethyl-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7-decadienyl)-5-hydroxy-, (E,E)-
InChi Key
JPWPYTMXSXYUPG-QZPYEDBESA-N
InChi Code
InChI=1S/C25H38O3/c1-18(11-7-13-21-17-23(26)28-24(21)27)9-6-10-19(2)14-15-22-20(3)12-8-16-25(22,4)5/h10-11,17,24,27H,6-9,12-16H2,1-5H3/b18-11+,19-10+
SMILES Code
O=C1OC(O)C(CC/C=C(C)/CC/C=C(C)/CCC2=C(C)CCCC2(C)C)=C1
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 386.58 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: Li J, Du L, Kelly M, Zhou YD, Nagle DG. Structures and potential antitumor activity of sesterterpenes from the marine sponge Hyrtios communis. J Nat Prod. 2013 Aug 23;76(8):1492-7. doi: 10.1021/np400350k. Epub 2013 Aug 14. PubMed PMID: 23944963; PubMed Central PMCID: PMC3809078. 2: McEwan IJ. What lies beneath: natural products from marine organisms as nuclear receptor modulators. Biochem J. 2012 Aug 15;446(1):e1-3. doi: 10.1042/BJ20121018. PubMed PMID: 22835216. 3: Wang S, Wang Z, Lin S, Zheng W, Wang R, Jin S, Chen J, Jin L, Li Y. Revealing a natural marine product as a novel agonist for retinoic acid receptors with a unique binding mode and inhibitory effects on cancer cells. Biochem J. 2012 Aug 15;446(1):79-87. doi: 10.1042/BJ20120726. PubMed PMID: 22642567. 4: Cao S, Foster C, Lazo JS, Kingston DG. Sesterterpenoids and an alkaloid from a Thorectandra sp. as inhibitors of the phosphatase Cdc25B. Bioorg Med Chem. 2005 Sep 1;13(17):5094-8. PubMed PMID: 15927472. 5: Elkhayat E, Edrada R, Ebel R, Wray V, van Soest R, Wiryowidagdo S, Mohamed MH, Müller WE, Proksch P. New luffariellolide derivatives from the Indonesian sponge Acanthodendrilla sp. J Nat Prod. 2004 Nov;67(11):1809-17. PubMed PMID: 15568767. 6: Froldi G, Galzignato G, Zanetti M, Montopoli M, Dorigo P, Caparrotta L. Are prostanoids related to positive inotropism by UTP and ATP? Pharmacology. 2005 Mar;73(3):140-5. Epub 2004 Nov 24. PubMed PMID: 15564788. 7: Glaser KB, Sung ML, Hartman DA, Lock YW, Bauer J, Walter T, Carlson RP. Cellular and topical in vivo inflammatory murine models in the evaluation of inhibitors of phospholipase A2. Skin Pharmacol. 1995;8(6):300-8. PubMed PMID: 8688196. 8: Marshall LA, Murphy J, Marinari L, Chang J. Characterization and pharmacological modulation of soluble phospholipase A2 generated during glycogen-induced rat peritonitis. Agents Actions. 1992 Sep;37(1-2):60-9. PubMed PMID: 1456181. 9: Mann J. Natural products. Sponges to wipe away pain. Nature. 1992 Aug 13;358(6387):540. PubMed PMID: 1501709. 10: Glaser KB, Lock YW, Chang JY. PAF and LTB4 biosynthesis in the human neutrophil: effects of putative inhibitors of phospholipase A2 and specific inhibitors of 5-lipoxygenase. Agents Actions. 1991 Sep;34(1-2):89-92. PubMed PMID: 1665306. 11: Calhoun W, Yu J, Sung A, Chau TT, Marshall LA, Weichman BM, Carlson RP. Pharmacologic modulation of D-49 phospholipase A2-induced paw edema in the mouse. Agents Actions. 1989 Jun;27(3-4):418-21. PubMed PMID: 2801333.