Achaetolide

Achaetolide

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Category Others
Catalog number BBF-00010
CAS
Molecular Weight 286.37
Molecular Formula C15H26O5

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Description

Achaetolide is an internal vinegar compound isolated from the Achaetamium cristalliferum PC 3252, A. strumarium (IMI 82624). Achaetolide has the effect of improving the transpiration of cut barley leaves.

Specification

Synonyms (3S,6R,7S,9R)-3,6,7,9-Tetrahydroxy-4-hexadecenoic acid 1,9-lactone
IUPAC Name (2R,4S,5R,6E,8S)-2-heptyl-4,5,8-trihydroxy-2,3,4,5,8,9-hexahydrooxecin-10-one
Canonical SMILES CCCCCCCC1CC(C(C=CC(CC(=O)O1)O)O)O
InChI InChI=1S/C16H28O5/c1-2-3-4-5-6-7-13-11-15(19)14(18)9-8-12(17)10-16(20)21-13/h8-9,12-15,17-19H,2-7,10-11H2,1H3/b9-8+/t12-,13-,14-,15+/m1/s1
InChI Key LAXPXFNVDQZXJE-ZVLUIJSYSA-N

Properties

Melting Point 122°C

Reference Reading

1. Chaetolines A and B, Pyrano[3,2- f]isoquinoline Alkaloids from Cultivation of Chaetomium sp. in the Presence of Autoclaved Pseudomonas aeruginosa
Elena Ancheeva, Attila Mándi, Sándor B Király, Tibor Kurtán, Rudolf Hartmann, Sergi H Akone, Horst Weber, Georgios Daletos, Peter Proksch J Nat Prod. 2018 Nov 26;81(11):2392-2398. doi: 10.1021/acs.jnatprod.8b00373. Epub 2018 Oct 21.
The first members of a new alkaloid class, chaetolines A (1) and B (2), which feature a pyrano[3,2- f]isoquinoline core structure, were obtained from a crude extract of the fungal endophyte Chaetomium sp. after cultivation in the presence of autoclaved Pseudomonas aeruginosa. The structures of the new compounds, including the absolute configuration of the major stereoisomer, were determined through detailed analysis of HRESIMS, 1D/2D NMR, and calculation of ECD data. The possible biosynthetic origin of the unprecedented scaffold of 1 and 2 is proposed. The current study provides further evidence for mixed fermentation as a powerful tool to induce the accumulation of cryptic fungal natural products even in the absence of viable bacterial cells.
2. Divergent Total Synthesis of Chaetoglines C to F
Yaocheng Shi, Zhi Xu, Renxiang Tan, Xiaoguang Lei J Org Chem. 2019 Jul 5;84(13):8766-8770. doi: 10.1021/acs.joc.9b01076. Epub 2019 Jun 25.
The first total syntheses of chaetoglines C-F via a bioinspired and divergent synthetic strategy are reported. Chaetolines C and D were obtained from the condensation of hemiacetal and tryptophan methyl ester building blocks followed by functional group transformations. The synthesis of chaetogline E employed the diastereoselective Pictet-Spengler reaction, and the tetrahydro-carboline skeleton was further utilized as a precursor for an oxidative aromatization reaction to introduce the β-carboline moiety of chaetogline F.

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