Bornesitol

Bornesitol
D-(−)-bornesitol
Names
IUPAC name
1D-1-O-Methyl-myo-inositol
Systematic IUPAC name
(1R,2R,3S,4S,5R,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
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-/m1/s1 checkY
    Key: DSCFFEYYQKSRSV-AGZHHQKVSA-N checkY
  • O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](OC)[C@H](O)[C@H]1O
Properties
C7H14O6
Molar mass 194.183 g·mol−1
Appearance white solid
Melting point 198–201 °C (388–394 °F; 471–474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bornesitol is an organic compound with the formula C7H14O6. Classified as a cyclitol (cyclic sugar alcohol), it is a methyl ether of D-myo-inositol.

It occurs in relative abundance in the leaves of Hancornia speciosa.

Biosynthesis

Both enantiomers of bornesitol are known and are biosynthesised from inositol. Inositol 1-methyltransferase catalyses the reaction:

2D representation of the chemical structure of inositol .
inositol
1-methylation
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q4946108.
(–)-bornesitol

Inositol 3-methyltransferase catalyses the reaction to the mirror image molecule:

inositol
 
3-methylation
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27103627.
(+)-bornesitol

References

  1. 1 2 Hofmann, Hilde; Wagner, Inge; Hoffmann-Ostenhof, Otto (1969). "Untersuchungen über die Biosynthese der Cyclite, XXIV. Über ein lösliches Enzym aus Vinca rosea , das myo -Inosit zu L-Bornesit methyliert" [Biosynthesis of cyclitols. XXIV. A soluble enzyme from Vinca rosea methylating myo-inositol to L-bornesitol]. Hoppe-Seyler's Zeitschrift für Physiologische Chemie (in German). 350 (2): 1465–1468. doi:10.1515/bchm2.1969.350.2.1465.
  2. ↑ Carneiro Junior, Wellerson de Oliveira; Guimarães, Maria Luiza Rocha; Freitas, Kátia Michelle; Pereira, Rosângela Santos; Pádua, Rodrigo Maia de; Campana, Priscilla Rodrigues Valadares; Braga, Fernão Castro (2024). "Structural characterization of a proanthocyanidin-rich fraction from Hancornia speciosa leaves and its effect on the release of pro-inflammatory cytokines and oxidative stress in THP-1 cells". Journal of Ethnopharmacology. 333 118471. doi:10.1016/j.jep.2024.118471. PMID 38901680.
  3. ↑ Norbert Schilling (1976). "Distribution of l-(+)-bornesitol in the gentianaceae and menyanthaceae". Phytochemistry. 15 (5): 824–826. Bibcode:1976PChem..15..824S. doi:10.1016/S0031-9422(00)94463-7.[dead link]