128252-98-2

Basic information

• Product Name: (6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-methyl-1-oxobutyl]-6aα-methyl-3-[(1E,3S)-3-methyl-1-pentenyl]-6H-furo[2,3-h]-2-benzopyran-6,8(6aH)-dione
• Synonyms: (6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-methyl-1-oxobutyl]-6aα-methyl-3-[(1E,3S)-3-methyl-1-pentenyl]-6H-furo[2,3-h]-2-benzopyran-6,8(6aH)-dione;Chaetoviridin A;5'-Hydroxychaetoviridine F
• CAS NO: 128252-98-2
• Molecular Formula: C23H25ClO6
• Molecular Weight: 432.894
• Mol File: 128252-98-2.mol

Chemical Properties

• Melting Point: 157-158℃
• Boiling Point: 607.6°C at 760 mmHg
• Flash Point: 321.3°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 2.67E-17mmHg at 25°C
• Refractive Index: 1.587
• PKA: 14.36±0.20(Predicted)
• CAS DataBase Reference: (6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-methyl-1-oxobutyl]-6aα-methyl-3-[(1E,3S)-3-methyl-1-pentenyl]-6H-furo[2,3-h]-2-benzopyran-6,8(6aH)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-methyl-1-oxobutyl]-6aα-methyl-3-[(1E,3S)-3-methyl-1-pentenyl]-6H-furo[2,3-h]-2-benzopyran-6,8(6aH)-dione(128252-98-2)
• EPA Substance Registry System: (6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-methyl-1-oxobutyl]-6aα-methyl-3-[(1E,3S)-3-methyl-1-pentenyl]-6H-furo[2,3-h]-2-benzopyran-6,8(6aH)-dione(128252-98-2)

Safety Data

• Hazardous Substances Data: 128252-98-2(Hazardous Substances Data)

Usage

Uses

Used in Antifungal Applications:
Chaetoviridin A is used as an antifungal agent for the inhibition of plant pathogenic fungi. Its unique structure and potent activity make it a promising candidate for the development of new antifungal agents to combat fungal infections in agriculture and horticulture.
Used in Pharmaceutical Industry:
Chaetoviridin A is used as a lead compound in the development of new drugs targeting various diseases. Its ability to inhibit MAO and CETP makes it a potential candidate for the treatment of various conditions, including cancer and other diseases.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of Chaetoviridin A, novel drug delivery systems can be developed. These systems can improve the delivery of the compound to target cells and tissues, increasing its therapeutic potential and reducing side effects.

InChI:InChI=1/C23H25ClO6/c1-6-11(2)7-8-14-9-15-16(10-29-14)18-17(20(26)12(3)13(4)25)22(28)30-23(18,5)21(27)19(15)24/h7-13,25H,6H2,1-5H3/b8-7+/t11-,12-,13+,23-/m0/s1

Upstream product

• 1403691-62-2 cazisochromene 
• 485-80-3 S-adenosyl-L-methionine 
• 1730-97-8 (S)-2-methylbutyraldehyde 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 34293-67-9 (+)-(2S,3R)-3-Hydroxy-2-methylbutansaeuremethylester 
• 250378-76-8 tert-Butyl syn-(4S,5R)-5-hydroxy-4-methyl-3-oxohexanoate 
• 4707-47-5 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester 
• 947-52-4 methyl 3-chloro-4,6-dihydroxy-2,5-dimethylbenzoate 

Relevant articles and documents

Total Synthesis and Structural Revision of Chaetoviridins A

The first synthesis of the proposed structures of chaetoviridins A 1-4 has been achieved in 10 steps by controlling the syn- or anti-aldol side chain. The angular lactone has been regioselectively introduced by condensation of a chiral dioxin-4-one to cazisochromene. Comparison of the NMR and circular dichroism data of the synthesized and reported natural products led to the complete reassignment and renaming of the chaetoviridins.

Expanding the structural diversity of polyketides by exploring the cofactor tolerance of an inline methyltransferase domain

A strategy for introducing structural diversity into polyketides by exploiting the promiscuity of an in-line methyltransferase domain in a multidomain polyketide synthase is reported. In vitro investigations using the highly-reducing fungal polyketide synthase CazF revealed that its methyltransferase domain accepts the nonnatural cofactor propargylic Se-adenosyl-l-methionine and can transfer the propargyl moiety onto its growing polyketide chain. This propargylated polyketide product can then be further chain-extended and cyclized to form propargyl-α pyrone or be processed fully into the alkyne-containing 4′-propargyl-chaetoviridin A.