Quebrachitol Explained

Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in Allophylus edulis^[1] and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping.^[2] It is also found in Cannabis sativa,^[3] in Paullinia pinnata and in seabuckthorn.^[4]

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.^[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, oudemansin X has been made.^[7]

External links

• Web site: Quebrachitol on the Sigma-Aldrich website . September 19, 2016 . https://web.archive.org/web/20121003153319/http://www.sigmaaldrich.com/catalog/product/aldrich/s404551?lang=en&region=US . October 3, 2012 . bot: unknown . mdy-all .

Notes and References

1. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TFF-4T3DCXV-2&_user=10&_coverDate=10%2F13%2F2008&_alid=1409665121&_rdoc=2&_fmt=high&_orig=search&_cdi=5225&_docanchor=&view=c&_ct=208&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=f07a2c756f27563c971ffcb07a3019cd First record of l-quebrachitol in Allophylus edulis (Sapindaceae). Martina Díaz, Andrés González, Ian Castro-Gamboa, David Gonzalez and Carmen Rossini, Carbohydrate Research, Volume 343, Issue 15, 13 October 2008, Pages 2699-2700
2. 10.1021/ie50493a041 . 43 . Quebrachitol . 1951 . Industrial & Engineering Chemistry . 141–145 . van Alphen . Jan.
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. 1252976 . 16745234 . 27 . 4. An investigation of quebrachitol as a sweetening agent for diabetics . 1933 . Biochem J . 986–9 . McCance . RA . Lawrence . RD . 10.1042/bj0270986.
6. 10.1021/cr00038a016 . 95 . 6 . Quebrachitol: A Versatile Building Block in the Construction of Naturally Occurring Bioactive Materials . 1995 . Chemical Reviews . 2189–2202 . Kiddle . James J..
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