Quebrachitol

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Chemical compound

title: "Quebrachitol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cyclitols"] description: "Chemical compound" topic_path: "general/cyclitols" source: "https://en.wikipedia.org/wiki/Quebrachitol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464378279 | Name = quebrachitol | ImageFile = L-quebrachitol.svg | ImageSize = | ImageName = Chemical structure of L-quebrachitol | ImageAlt = Chemical structure of quebrachitol | IUPACName = (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol | OtherNames = Quebrachitol L-Quebrachitol (-)-Quebrachitol 2-O-methyl-l-inositol 2-0-methyl-chiro-inositol |Section1={{Chembox Identifiers | CASNo = 642-38-6 | CASNo_Ref = | CASNoOther = | UNII_Ref = | UNII = 9W4JLQ7I4W | PubChem = 151108 | ChEMBL_Ref = | ChEMBL = 501109 | ChemSpiderID_Ref = | ChemSpiderID = 10254652 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = DSCFFEYYQKSRSV-FIZWYUIZSA-N | SMILES = CO[C@H]1C@@HO | InChI = | MeSHName = |Section2={{Chembox Properties | Formula = C7H14O6 | MolarMass = 194.18 g/mol | Appearance = White to off-white powder | Density = | MeltingPtC = 190 to 198 | MeltingPt_notes = | BoilingPt = | Solubility = Soluble in DMSO, dimethyl formamide, or water 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]

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cyclitols