2α,9α,11-Trihydroxy-6-oxodrim-7-ene

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2α,9α,11-Trihydroxy-6-oxodrim-7-ene
Category Others
Catalog number BBF-04370
CAS 1175543-03-9
Molecular Weight 268.35
Molecular Formula C15H24O4
Purity 97.5%

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BBF-04370 1 mg $629 In stock

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Description

2α,9α,11-Trihydroxy-6-oxodrim-7-ene is produced from the culture medium of the marine-derived fungus Aspergillus insuetus.

Specification

Synonyms 2alpha,9alpha,11-trihydroxy-6-oxodrim-7-ene; 1(4H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-4,6-dihydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-, (4R,4aS,6S,8aS)-
Storage Store at 2-8°C
IUPAC Name (4R,4aS,6S,8aS)-4,6-dihydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydronaphthalen-1-one
Canonical SMILES CC1=CC(=O)C2C(CC(CC2(C1(CO)O)C)O)(C)C
InChI InChI=1S/C15H24O4/c1-9-5-11(18)12-13(2,3)6-10(17)7-14(12,4)15(9,19)8-16/h5,10,12,16-17,19H,6-8H2,1-4H3/t10-,12-,14-,15+/m0/s1
InChI Key MMMVWBXLRFTTSV-HQRZJTNHSA-N

Properties

Appearance Powder
Boiling Point 436.8±45.0°C (Predicted)
Density 1.165±0.06 g/cm3 (Predicted)
Solubility Soluble in Methanol

Reference Reading

1. Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel
Elazar Cohen, Liat Koch, Kathy Myint Thu, Yocheved Rahamim, Yaniv Aluma, Micha Ilan, Oded Yarden, Shmuel Carmeli Bioorg Med Chem. 2011 Nov 15;19(22):6587-93. doi: 10.1016/j.bmc.2011.05.045. Epub 2011 May 30.
Three novel meroterpenoids, insuetolides A-C (1-3) and four drimane sesquiterpenes, the new (E)-6-(4'-hydroxy-2'-butenoyl)-strobilactone A (4) and the known 2α, 9α, 11-trihydroxy-6-oxodrim-7-ene (5), strobilactone A (6) and (E,E)-6-(6',7'-dihydroxy-2',4'-octadienoyl)-strobilactone A (7), were isolated from the EtOAc extract of the culture medium of the marine-derived fungus Aspergillus insuetus (OY-207), which was isolated from the Mediterranean sponge Psammocinia sp. The structures of the compounds were determined by spectroscopic methods. Insuetolides A-C reveal a new carbon skeleton derived from the cyclization of farnesyl and 3, 5-dimethylorsellinic acid. Compounds 1, 6, and 7 exhibited anti-fungal activity towards Neurospora crassa with MIC values of 140, 242, and 162 μM, respectively; and compounds 3, 4, and 7 exhibited mild cytotoxicity towards MOLT-4 human leukemia cells.

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