Cacospongionolide B | CAS# 172854-76-1 | inflammation

MedKoo Cat#: 412219 | Name: Cacospongionolide B

Description:

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

Cacospongionolide B is isolated from the sponge Fasciospongia cavernosa. The marine sponge natural product cacospongionolide B (1) is one of a class of compounds bearing a g-hydroxybutenolide which are known to inhibit multiple forms of secratory phospholipase A2,1 enzymes believed to initiate a cascade of biological events leading to inflammation.

Chemical Structure

Cacospongionolide B

CAS#172854-76-1

Theoretical Analysis

MedKoo Cat#: 412219

Name: Cacospongionolide B

CAS#: 172854-76-1

Chemical Formula: C25H36O4

Exact Mass: 400.2614

Molecular Weight: 400.56

Elemental Analysis: C, 74.96; H, 9.06; O, 15.98

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 #

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Synonym

Cacospongionolide B

IUPAC/Chemical Name

2(5H)-Furanone, 4-((2R)-5-(2-((1S,2S,4aR,8aR)-decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)ethyl)-3,6-dihydro-2H-pyran-2-yl)-5-hydroxy-,(5R)-

InChi Key

CVAZWHZRZNYCOV-DRCQBYJMSA-N

InChi Code

InChI=1S/C25H36O4/c1-16-6-5-7-21-24(16,3)12-10-17(2)25(21,4)13-11-18-8-9-20(28-15-18)19-14-22(26)29-23(19)27/h8,14,17,20-21,23,27H,1,5-7,9-13,15H2,2-4H3/t17-,20+,21-,23+,24-,25-/m0/s1

SMILES Code

O=C1O[C@@H](O)C([C@H]2CC=C(CC[C@@]3(C)[C@@H](C)CC[C@@]4(C)C(CCC[C@]34[H])=C)CO2)=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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 400.56 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: De Stefano D, Tommonaro G, Malik SA, Iodice C, De Rosa S, Maiuri MC, Carnuccio R. Cacospongionolide and scalaradial, two marine sesterterpenoids as potent apoptosis-inducing factors in human carcinoma cell lines. PLoS One. 2012;7(4):e33031. doi: 10.1371/journal.pone.0033031. Epub 2012 Apr 3. PMID: 22509253; PMCID: PMC3317917. 2: Murelli RP, Cheung AK, Snapper ML. Conformationally restricted (+)-cacospongionolide B analogues. Influence on secretory phospholipase A2 inhibition. J Org Chem. 2007 Mar 2;72(5):1545-52. doi: 10.1021/jo061407a. PMID: 17315974. 3: Alcaraz MJ, Payá M. Marine sponge metabolites for the control of inflammatory diseases. Curr Opin Investig Drugs. 2006 Nov;7(11):974-9. PMID: 17117584. 4: Cheung AK, Murelli R, Snapper ML. Total syntheses of (+)- and (-)-cacospongionolide B, cacospongionolide e, and related analogues. Preliminary study of structural features required for phospholipase a2 inhibition. J Org Chem. 2004 Aug 20;69(17):5712-9. doi: 10.1021/jo049285e. PMID: 15307744. 5: Posadas I, De Rosa S, Terencio MC, Payá M, Alcaraz MJ. Cacospongionolide B suppresses the expression of inflammatory enzymes and tumour necrosis factor- alpha by inhibiting nuclear factor-kappa B activation. Br J Pharmacol. 2003 Apr;138(8):1571-9. doi: 10.1038/sj.bjp.0705189. PMID: 12721113; PMCID: PMC1573800. 6: Cheung AK, Snapper ML. Total syntheses of (+)- and (-)-cacospongionolide B: new insight into structural requirements for phospholipase A(2) inhibition. J Am Chem Soc. 2002 Oct 2;124(39):11584-5. doi: 10.1021/ja026899x. PMID: 12296709. 7: De Rosa S, Crispino A, De Giulio A, Iodice C, Amodeo P, Tancredi T. A new cacospongionolide derivative from the sponge Fasciospongia cavernosa. J Nat Prod. 1999 Sep;62(9):1316-8. doi: 10.1021/np990125l. PMID: 10514323. 8: García Pastor P, De Rosa S, De Giulio A, Payá M, Alcaraz MJ. Modulation of acute and chronic inflammatory processes by cacospongionolide B, a novel inhibitor of human synovial phospholipase A2. Br J Pharmacol. 1999 Jan;126(1):301-11. doi: 10.1038/sj.bjp.0702302. PMID: 10051149; PMCID: PMC1565805. 9: De Rosa M, Giordano S, Scettri A, Sodano G, Soriente A, Pastor PG, Alcaraz MJ, Payá M. Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues. J Med Chem. 1998 Aug 13;41(17):3232-8. doi: 10.1021/jm980027h. PMID: 9703468. 10: De Rosa S, Crispino A, De Giulio A, Iodice C, Pronzato R, Zavodnik N. Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa. J Nat Prod. 1995 Nov;58(11):1776-80. doi: 10.1021/np50125a024. PMID: 8594155.