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. Author manuscript; available in PMC: 2008 Nov 13.
Published in final edited form as: Acta Crystallogr Sect E Struct Rep Online. 2007;63(2):o1067–o1068. doi: 10.1107/S1600536806037019

L-(+)-Bornesitol

Denise C Endringer a, John M Pezzuto b, Cristiane M Soares a, Fernão C Braga a
PMCID: PMC2582817  NIHMSID: NIHMS67925  PMID: 19011691

Abstract

The structure of the title compound, C7H14O6, one natural myo-inositol derivative has been determinaded. Average atom distances, bond lengths and dihedral angles are similar to myo-inositol.

Comment

Bornesitol (I) is a myo-inositol methyl derivative found in several plant species (Girard, 1871; Nishibe et al., 2001), its chemical structure has been previously described (Foster & Stacey, 1953, Bien & Ginsburg, 1958). myo-Inositol (II) is a cyclitol which has only one axial-oriented hydroxyl group (C2) and has mirror symmetry (Rabinowitz & Kraut, 1964, Bonnet et al., 2006).

As part of our study of plant products, we report here the absolute structure for one of bornesitol enantiomers. The analyzed crystal belongs to the dextrorotatory enantiomer, with [α]D= +20.7 ± 3.5°, a value similar to those previously described for bornesitol (Angyal & Bender, 1961). Bornesitol crystallizes in the orthorhombic space group P212121. The dimension of (I) is similar to myo-inositol (II) (Rabinowitz & Kraut, 1964), but it has non-centrosymmetric structures (Fig. 1). The intermolecular O⋯H distances range from 1.78 to 2.03 Å (Table 1) and are less than the intramolecular O⋯O distances (from 2.67 to 2.89 Å), in contrast to other cyclitols that present similar values (Rabinowitz & Kraut, 1964; Hosomi et al., 2000, Bonnet et al., 2006). The angle between O3—H3⋯O1 is ca 10° less than O6—H6⋯O4, and a minor difference is noted between O2—H2⋯O6 and O4—H4⋯H2 (Table 1).

Figure 1.

Figure 1

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ORTEP plot of L-(+)-bornesitol, showing atomic notation and thermal ellipsoids. The molecule is viewed approximately normal to the center plane of the chair-shaped cyclohexane ring: C2 and C5 are below and above the plane, respectively. Thermal ellipsoids are shown at the 50% probability level for non-H atoms.

Table 1.

Hydrogen-bond geometry (A% , °)

D H A D-H A-H D-A D-H-A
O2 H2 O6 0.86 (3) 1.82 (2) 2.667 (3) 170 (3)
O3 H3 O1 0.95 (3) 1.80 (3) 2.723 (3) 162 (3)
O4 H4 O2 0.87 (3) 1.84 (3) 2.695 (3) 167 (3)
O5 H5 O3 0.89 (3) 2.03 (3) 2.892 (3) 163 (3)
O6 H6 O4 0.90 (3) 1.80 (3) 2.688 (2) 171 (3)
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The absolute structure of (+)-bornesitol was estimated based on the known absolute configuration of the title compound (Angyal; Gilman, 1957), as (1R)-O-methyl-myo-inositol. According to IUPAC recommendations for nomenclature of inositol derivatives, which names L-bornesitol as 1-O-methyl-myo-inositol, with clockwise numbering, (+)-bornesitol should be denominated (1R)-1-L-O-methyl-myo-inositol (Angyal et al., 1992).

Experimental

Compound (I) was obtained from the EtOAc:MeOH (4.5:5.5) fraction of Hancornia speciosa leaves (Apocynaceae). The crude fraction was dissolved in methanol:water (9:1) and the solution was kept at room temperature. Crystals of (I) grew as colourless prisms from this solution by slow evaporation. Optical rotation was determined for a water solution (0.11 g/100 ml) of compound (I), in a Perkin Elmer polarimeter-341 at 589 nm and 20° C, using a 100 mm path length cell.

Crystal data
C7H14O6 Dx = 1.521 Mg m−3
Mr = 194.19 Mo - Kα radiation
Orthorhombic, P212121 Cell parameters from 5715 reflections
a = 6.5756 (4) Å θ = 3–27°
b = 11.0565 (7) Å μ = 0.13 mm−1
c = 11.6622 (9) Å T = 150 K
V = 847.88 (10) Å3 Plate, colourless
Z = 4 0.48 × 0.44 × 0.23 mm
Data collection
Nonius KappaCCD diffractometer 1151 independent reflections
ω scans 974 reflections with > 2.0σ(I)
Absorption correction:
multi-scan
(Otowinwski & Minor, 1997)		 Rint = 0.035
Tmin = 0.926, Tmax = 0.972 θmax = 27.5°
5715 measured reflections
Refinement
Refinement on F2 1/[σ2(Fo2) + (0.0543P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.034 (Δ/σ)max < 0.001
wR(F2) = 0.085 Δρmax = 0.19 e Å−3
S = 1.05 Δρmin = −0.20 e Å−3
1151 reflections Extinction correction: SHELXL97 (Sheldrick 1997)
140 parameters Extinction coefficient: 0.036 (5)
H atoms treated by a mixture of independent and constrained refinement
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The structure was solved by direct methods using SIR2004 (Burla et al., 2005). The remaining atoms were located in succeeding difference Fourier syntheses. Hydrogen atoms were included in the structure factor calculation in idealized positions using the riding model but they were not refined. The structure was refined in full-matrix least-squares where the function minimized was ©w(|Fo|2-|Fc|2)2 and the weight w is defined as 1/[ ⎧2(Fo2)+(0.0461P)2+0.0000P] where P=(Fo2+2Fc2)/3. Scattering factors were taken from the “International Tables for Crystallography”.

graphic file with name nihms67925f2.jpg

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Acknowledgments

CNPq/Brazil (Conselho Nacional de Desenvolvimento Científico e Tecnológico) is acknowledged for undergraduate (C.M.S.) and research fellowships (F.C.B.). CAPES/Brazil (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) supported this project with a Ph.D. fellowship (D.C.E.). The work was also supported by program project grant P01 CA48112 awarded by the National Cancer Institute. Dr. Júlio Antônio Lombardi is acknowledged for collecting the plant material.

Footnotes

Data collection: Collect (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1996); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1996); program(s) used to solve structure: Direct methods (SIR2004, Burla et al., 2005); program(s) used to refine structure: SHELX97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1976) PLATON (Spek, 1997); software used to prepare material for publication: SHELX97(Sheldrick, 1997) and local programs.

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