Quebrachitol

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]

quebrachitol
Chemical structure of quebrachitol
Names
IUPAC name
(1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
Other names
Quebrachitol
L-Quebrachitol
(-)-Quebrachitol
2-O-methyl-l-inositol
2-0-methyl-chiro-inositol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1 checkY
    Key: DSCFFEYYQKSRSV-FIZWYUIZSA-N checkY
  • CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H]([C@H]1O)O)O)O)O
Properties
C7H14O6
Molar mass 194.18 g/mol
Appearance White to off-white powder
Melting point 190 to 198 °C (374 to 388 °F; 463 to 471 K)
Soluble in DMSO, dimethyl formamide, or water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

References
  1. 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, Read More}}
  2. van Alphen, Jan (1951). "Quebrachitol". Industrial & Engineering Chemistry. 43: 141–145. doi:10.1021/ie50493a041.
  3. 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. 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. 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. PMC 1252976. PMID 16745234.
  6. 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.
  7. 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
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