Cyathin A4

Cyathin A4

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Category Antibiotics
Catalog number BBF-01102
CAS
Molecular Weight 334.45
Molecular Formula C20H30O4

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Description

It is produced by the strain of Cyathus helenae, C. africanus. It has weak activity against gram-positive bacteria, negative bacteria, actinomycetes and dermatophytes, and has anti-ischemia effect (improving cerebral ischemia in rat model).

Specification

IUPAC Name (3aR,5aR,9R,10aR)-9-hydroxy-8-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-3a,5a-dimethyl-3,4,5,9,10,10a-hexahydro-2H-cyclohepta[e]inden-6-one
Canonical SMILES CC(CO)C1=C2C3CC(C(=CC(=O)C3(CCC2(CC1)C)C)CO)O
InChI InChI=1S/C20H30O4/c1-12(10-21)14-4-5-19(2)6-7-20(3)15(18(14)19)9-16(23)13(11-22)8-17(20)24/h8,12,15-16,21-23H,4-7,9-11H2,1-3H3/t12?,15-,16-,19-,20-/m1/s1
InChI Key SBABRWMIXWNDTO-YXDXTEDTSA-N

Properties

Appearance Clear Oily Matter
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Fungi

Reference Reading

1. Enantioselective total synthesis of cyathin A3
Dale E Ward, Jianheng Shen Org Lett. 2007 Jul 19;9(15):2843-6. doi: 10.1021/ol070994z. Epub 2007 Jun 20.
The total synthesis of (-)-cyathin A3 is described. The key step involves an unusual enantioselective Diels-Alder reaction of 2,5-dimethyl-1,4-benzoquinone with 2,4-bis(trimethylsilyloxy)-1,3-pentadiene, using Mikami's catalyst [(R)-BINOL + Cl2Ti(OiPr)2 + 4 A mol sieves] modified by addition of Mg and SiO2. Because cyathin A3 is easily transformed into allocyathin B3, cyathin B3, cyathin C3, and neoallocyathin A4, this route also constitutes formal syntheses of these natural products.

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L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
g

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