Synonym
Marasmic acid; NSC 318506; NSC-318506; NSC318506; LACHNELLA FUNGUS; CCRIS 1701;
IUPAC/Chemical Name
(3S,3aR,5aR,8aS,8bS)-3-hydroxy-7,7-dimethyl-1-oxo-5a,7,8,8a-tetrahydro-1H,3H,6H-3a,8b-methanoindeno[4,5-c]furan-4-carbaldehyde
InChi Key
BIUVCPLWWOLECJ-TVXZTZGSSA-N
InChi Code
InChI=1S/C15H18O4/c1-13(2)4-8-3-9(6-16)14-7-15(14,10(8)5-13)12(18)19-11(14)17/h3,6,8,10-11,17H,4-5,7H2,1-2H3/t8-,10-,11-,14-,15+/m0/s1
SMILES Code
O=CC1=C[C@@H]2[C@H](CC(C)(C2)C)[C@@]3([C@]1(C3)[C@H](O4)O)C4=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
262.30
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: Jacob S, Schüffler A, Thines E. Hog1p activation by marasmic acid through inhibition of the histidine kinase Sln1p. Pest Manag Sci. 2016 Jun;72(6):1268-74. doi: 10.1002/ps.4257. Epub 2016 Mar 22. PubMed PMID: 26888741; PubMed Central PMCID: PMC5071701.
2: Kupka J, Anke T, Mizumoto K, Giannetti BM, Steglich W. Antibiotics from basidiomycetes. XVII. The effect of marasmic acid on nucleic acid metabolism. J Antibiot (Tokyo). 1983 Feb;36(2):155-60. PubMed PMID: 6300012.
3: DUGAN JJ, DE MAYO P, NISBET M, ANCHEL M. MARASMIC ACID. J Am Chem Soc. 1965 Jun 20;87:2768-9. PubMed PMID: 14292180.
4: Dugan JJ, de Mayo P, Nisbet M, Robinson JR, Anchel M. Terpenoids. XIV. The constitution and biogenesis of marasmic acid. J Am Chem Soc. 1966 Jun 20;88(12):2838-44. PubMed PMID: 5941267.
5: Wilson SR, Turner RB. Studies in sesquiterpene synthesis. The marasmic acid skeleton. J Org Chem. 1973 Aug 10;38(16):2870-3. PubMed PMID: 4739032.
6: Heim J, Anke T, Mocek U, Steffan B, Steglich W. Antibiotics from basidiomycetes. XXIX: Pilatin, a new antibiotically active marasmane derivative from cultures of Flagelloscypha pilatii agerer. J Antibiot (Tokyo). 1988 Dec;41(12):1752-7. PubMed PMID: 3209467.
