# Quebrachitol

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Quebrachitol
> Markdown URL: https://mediated.wiki/source/Quebrachitol.md
> Source: https://en.wikipedia.org/wiki/Quebrachitol
> Source revision: 1291891675
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

**Quebrachitol** is a naturally occurring optically active [cyclitol](/source/Cyclitol), a cyclic polyol. It can be found in *[Allophylus edulis](/source/Allophylus_edulis)*[1] and in the serum left after the coagulation of the *[Hevea brasiliensis](/source/Hevea_brasiliensis)* latex in the operation of [rubber tapping](/source/Rubber_tapping).[2] It is also found in *[Cannabis sativa](/source/Cannabis_sativa)*,[3] in *[Paullinia pinnata](/source/Paullinia_pinnata)* and in [seabuckthorn](/source/Seabuckthorn).[4]

It was first isolated by [Tanret](/source/Charles_Joseph_Tanret) in 1887 from the bark of *[Aspidosperma quebracho](/source/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](/source/Diarrhoea) at concentration used to render the food palatable.[5]

Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials.[6] For example, its conversion into antifungal [(E)-β-methoxyacrylate](/source/Methoxyacrylates), [oudemansin X](/source/Oudemansin_X) has been made.[7]

## References

1. Díaz, Martina; González, Andrés; Castro-Gamboa, Ian; Gonzalez, David; Rossini, Carmen (13 October 2008). ["First record of l-quebrachitol in Allophylus edulis (Sapindaceae)"](https://www.sciencedirect.com/science/article/abs/pii/S0008621508003649). *Carbohydrate Research*. **343** (15): 2699–2700. [doi:10.1016/j.carres.2008.07.014](https://doi.org/10.1016/j.carres.2008.07.014). [PMID 18715552](https://pubmed.ncbi.nlm.nih.gov/18715552)

1. van Alphen, Jan (1951). "Quebrachitol". *Industrial & Engineering Chemistry*. **43**: 141–145. [doi:10.1021/ie50493a041](https://doi.org/10.1021/ie50493a041)

1. [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](http://www.bushka.cz/KabelikEN/proprieties.html)

1. [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](http://www.sanddorn.net/abstracts/shipulina_1.htm)

1. McCance, RA & Lawrence, RD (1933). "An investigation of quebrachitol as a sweetening agent for diabetics". *Biochem J*. **27** (4): 986–9. [doi:10.1042/bj0270986](https://doi.org/10.1042/bj0270986). [PMC 1252976](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1252976). [PMID 16745234](https://pubmed.ncbi.nlm.nih.gov/16745234)

1. Kiddle, James J. (1995). "Quebrachitol: A Versatile Building Block in the Construction of Naturally Occurring Bioactive Materials". *Chemical Reviews*. **95** (6): 2189–2202. [doi:10.1021/cr00038a016](https://doi.org/10.1021/cr00038a016)

1. [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](http://cat.inist.fr/?aModele=afficheN&cpsidt=5522212)

## External links

- ["Quebrachitol on the Sigma-Aldrich website"](http://www.sigmaaldrich.com/catalog/product/aldrich/s404551?lang=en&region=US). [Archived](https://web.archive.org/web/20121003153319/http://www.sigmaaldrich.com/catalog/product/aldrich/s404551?lang=en&region=US) October 3, 2012 at the Wayback Machine. Retrieved September 19, 2016.

---
Adapted from the Wikipedia article [Quebrachitol](https://en.wikipedia.org/wiki/Quebrachitol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Quebrachitol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.