Surf Wiki
Save to docs
general/cyclitols

From Surf Wiki (app.surf) — the open knowledge base

Quebrachitol

Chemical compound

Chemical compound

L-Quebrachitol (-)-Quebrachitol 2-O-methyl-l-inositol 2-0-methyl-chiro-inositol Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in Allophylus edulis and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping. It is also found in Cannabis sativa, in Paullinia pinnata and in seabuckthorn.

It was first isolated by Tanret in 1887 from the bark of Aspidosperma quebracho. The substance was tested as a sweetening agent for diabetics in 1933. It shows a sweetening property half of that of sucrose but induces colic or diarrhoea at concentration used to render the food palatable.

Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made.

References

References

  1. (13 October 2008). "First record of l-quebrachitol in Allophylus edulis (Sapindaceae)". Carbohydrate Research.
  2. (1951). "Quebrachitol". Industrial & Engineering Chemistry.
  3. [http://www.bushka.cz/KabelikEN/proprieties.html 1955 - ACTA UNIVERSITATIS PALACKIANAE OLOMUCENSIS - TOM. VI. - HEMP AS A MEDICAMENT, Properties of isolated substances. Prof. Jan Kabelik, A brief survey of the methods of isolation and the physical and chemical properties and structures of the isolated antibacterial substances. F. Santavy & Z. Krejci]
  4. [http://www.sanddorn.net/abstracts/shipulina_1.htm Some new data about antiviral and related activities of seabuckthorn principals and the prospects of their use. Shipulina L.D., All-Russian Research Institute of Medicinal and Aromatic Plants, Moscow, Russia]
  5. (1933). "An investigation of quebrachitol as a sweetening agent for diabetics". Biochem J.
  6. (1995). "Quebrachitol: A Versatile Building Block in the Construction of Naturally Occurring Bioactive Materials". Chemical Reviews.
  7. [http://cat.inist.fr/?aModele=afficheN&cpsidt=5522212 Total synthesis of antibiotic (−)-oudemansin X utilizing L-quebrachitol as a chiral pool. Chida N., Yamada K. and Ogawa S., Chemistry Letters, 1992, no4, pp. 687-690]
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

cyclitols
Want to explore this topic further?

Ask Mako anything about Quebrachitol — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report