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MedKoo Cat#: 558766 | Name: Luffolide

Description:

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

Luffolide is a minor metabolite of the sponge Luffariella sp. Luffolide has some of the anti-inflammatory properties of manoalide : this may help to define the chemical reaction between manoalide and phospholipase A2. The hydrolisis of phosphatidyl choline PLA2 is completely inhibitted by Luffolide.

Chemical Structure

Luffolide
Luffolide
CAS#121449-94-3

Theoretical Analysis

MedKoo Cat#: 558766

Name: Luffolide

CAS#: 121449-94-3

Chemical Formula: C27H40O6

Exact Mass: 460.2800

Molecular Weight: 460.61

Elemental Analysis: C, 70.41; H, 8.75; O, 20.84

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 #
121449-94-3
Synonym
Luffolide
IUPAC/Chemical Name
[(1R)-2-[(1R,2S,4aS,4bS,8aS,10aS)-2-formyl-4b,8,8,10a-tetramethyl-2,3,4,4a,5,6,7,8a,9,10-decahydro-1H-phenanthren-1-yl]-1-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]ethyl] acetate
InChi Key
QPTVAYUFYIWGFW-QRDIJWGLSA-N
InChi Code
1S/C27H40O6/c1-16(29)32-20(18-13-23(30)33-24(18)31)14-19-17(15-28)7-8-22-26(19,4)12-9-21-25(2,3)10-6-11-27(21,22)5/h13,15,17,19-22,24,31H,6-12,14H2,1-5H3/t17-,19-,20-,21+,22+,24-,26+,27+/m1/s1
SMILES Code
CC(=O)O[C@H](C[C@@H]1[C@H](CC[C@H]2[C@]1(CC[C@@H]3[C@@]2(CCCC3(C)C)C)C)C=O)C4=CC(=O)O[C@H]4O
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 460.61 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: Mann J. Natural products. Sponges to wipe away pain. Nature. 1992 Aug 13;358(6387):540. PubMed PMID: 1501709. 2: Basabe P, Delgado S, Marcos IS, Diez D, Diego A, De Román M, Urones JG. Synthesis of three marine natural sesterterpenolides from methyl isoanticopalate. First enantioselective synthesis of luffolide. J Org Chem. 2005 Nov 11;70(23):9480-5. PubMed PMID: 16268623. 3: Kernan MR, Faulkner DJ, Parkanyi L, Clardy J, de Carvalho MS, Jacobs RS. Luffolide, a novel anti-inflammatory terpene from the sponge Luffariella sp.. Experientia. 1989 Apr 15;45(4):388-90. PubMed PMID: 2707379.