CAS 21879-81-2

(5S,6R,7S)-5,6,7,8-Tetrahydro-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4-anthracenedione

Description:

The chemical substance known as (5S,6R,7S)-5,6,7,8-Tetrahydro-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4-anthracenedione, with the CAS number 21879-81-2, is a complex organic compound belonging to the anthraquinone family. This compound features multiple hydroxyl groups, which contribute to its solubility and reactivity, making it potentially useful in various chemical applications. The presence of a methoxy group enhances its hydrophobic characteristics while also influencing its electronic properties. The stereochemistry indicated by the (5S,6R,7S) configuration suggests specific spatial arrangements of its substituents, which can significantly affect its biological activity and interaction with other molecules. Such compounds are often studied for their potential pharmacological properties, including anti-inflammatory and antioxidant activities. Additionally, the intricate structure may allow for various synthetic modifications, making it a candidate for further research in medicinal chemistry and materials science. Overall, this compound exemplifies the complexity and diversity of organic molecules in chemical research.

Formula: C₁₆H₁₆O₈

InChI: InChI=1S/C16H16O8/c1-16(23)4-5-8(14(21)15(16)22)13(20)9-6(17)3-7(24-2)12(19)10(9)11(5)18/h3,14-15,18,20-23H,4H2,1-2H3/t14-,15+,16-/m0/s1

InChI key: InChIKey=ZQNOLGRKZRDRQO-XHSDSOJGSA-N

SMILES: OC1=C2C(=C(O)C3=C1C(=O)C=C(OC)C3=O)C[C@](C)(O)[C@H](O)[C@H]2O

Synonyms:

• Anthraquinone, 1,2,3,4-tetrahydro-1β,2β,3β,5,8-pentahydroxy-6-methoxy-3-methyl-
• 1,4-Anthracenedione, 5,6,7,8-tetrahydro-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-, [5S-(5α,6β,7β)]-
• (5S,6R,7S)-5,6,7,8-Tetrahydro-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4-anthracenedione
• Bostrycin
• 1,4-Anthracenedione, 5,6,7,8-tetrahydro-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-, (5S,6R,7S)-

Bostrycin

CAS: 21879-81-2

Bostrycin, an anthraquinone derived from B. alpestre, exhibits a broad spectrum of biological activities including antibacterial, antiproliferative, and phytotoxic effects. This compound demonstrates efficacy against Gram-positive bacteria like methicillin-resistant S. aureus (MRSA), M. tuberculosis, and C. botulinum. Additionally, Bostrycin shows antiproliferative action against A549 lung adenocarcinoma cells, particularly by arresting the cell cycle at the G0/G1 phase and triggering apoptosis within a concentration range of 10 to 30 µM. As a phytotoxin, it causes necrosis in water hyacinth leaves at approximately 7 µg/ml. Furthermore, Bostrycin serves as a protein immobilization cross-linking agent, managing to preserve its bacteriostatic properties when affixed to nonwoven polypropylene fabric.

Formula: C₁₆H₁₆O₈

Color and Shape: Solid

Molecular weight: 336.29

Ref: TM-TN7550

Bostrycin

CAS: 21879-81-2

Ref: 7W-GW5061

Bostrycin

CAS: 21879-81-2

Bostrycin is a polyketide-type natural product, which is a secondary metabolite produced by certain fungi, particularly those belonging to the genus Aschersonia. Its source lies in the complex biosynthetic pathways of these fungi, which synthesize diverse polyketides with bioactive properties. The mode of action of Bostrycin involves disrupting cellular processes, predominantly through the inhibition of specific enzyme activities and interference with DNA processes, which can lead to cell cycle arrest and apoptosis in target cells.

Formula: C₁₆H₁₆O₈

Purity: Min. 95%

Molecular weight: 336.29 g/mol

Ref: 3D-WAA87981