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
CAS Number	484-71-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18427 ;
ChemSpider	10254649 ;
KEGG	C03659;
PubChem CID	440078;
UNII	RW8AP5YP8U ;
CompTox Dashboard (EPA)	DTXSID60331468 ;
	InChI 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 Key: DSCFFEYYQKSRSV-AGZHHQKVSA-N ;
	SMILES O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](OC)[C@H](O)[C@H]1O;
Properties
Chemical formula	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). Infobox references

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.^[1]

It occurs in relative abundance in the leaves of Hancornia speciosa.^[2]^[3]

Biosynthesis

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

1-methylation

(–)-bornesitol

Inositol 3-methyltransferase catalyses the reaction to the mirror image molecule:^[1]

inositol

3-methylation

(+)-bornesitol

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.
↑ 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.
↑ 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]}

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