Methyl eucomate

Linglin Li; Guang-Xiong Zhou; Ren-Wang Jiang

doi:10.1107/S1600536808018734

. 2008 Jun 28;64(Pt 7):o1354. doi: 10.1107/S1600536808018734

Methyl eucomate

Linglin Li ^a, Guang-Xiong Zhou ^b, Ren-Wang Jiang ^b,^*

PMCID: PMC2961689 PMID: 21202973

Abstract

The crystal structure of the title compound [systematic name: methyl 3-carboxy-3-hydroxy-3-(4-hydroxybenzyl)propanoate], C₁₂H₁₄O₆, is stabilized by intermolecular O—H⋯O and C—H⋯O hydrogen bonds. The molecules are arranged in layers, parallel to (001), which are interconnected by the O—H⋯O hydrogen bonds.

Related literature

For related literature, see: Heller & Tamm (1974 ▶); Jiang et al. (2002 ▶, 2006 ▶).

Experimental

Crystal data

C₁₂H₁₄O₆
M _r = 254.23
Orthorhombic,
a = 5.9109 (6) Å
b = 7.0348 (7) Å
c = 29.109 (3) Å
V = 1210.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 (2) K
0.40 × 0.32 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
6709 measured reflections
1279 independent reflections
1047 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.066
S = 1.05
1278 reflections
168 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT and XPREP in SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018734/fb2096sup1.cif

e-64-o1354-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018734/fb2096Isup2.hkl

e-64-o1354-Isup2.hkl^{(63.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.82	1.96	2.775 (2)	172
O2—H2⋯O1ⁱⁱ	0.82	2.33	2.888 (2)	125
O4—H4⋯O2ⁱⁱⁱ	0.82	1.85	2.639 (2)	161
C12—H12B⋯O5^iv	0.96	2.42	3.268 (4)	148

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

This work was supported by the Starting Fund for Excellent Talents of Jinan University.

supplementary crystallographic information

Comment

Methyl eucomate is the methyl ester of the eucomic acid. The title compound has been isolated from several edible plants, e. g. Opuntia dillenii (Jiang et al., 2006) or Opuntia vulgaris (Jiang et al., 2002). However, the stereochemistry of the ester has not been established yet. In the present paper, we report its crystal structure.

The molecule contains phenol, carboxyl, ester and hydroxyl functional groups (Fig. 1). The mean deviation of the benzene ring from planarity is 0.0004 Å and its dihedral angle with the plane of the carboxylic group at C8 is 50.3 (3)°, while it is roughly perpendicular to the ester group at C10 with a dihedral angle of 87.3 (3)°.

The intermolecular hydrogen bonds O1—H···O3, O2—H···O1 and O4—H···O2 (Tab. 1) link the molecules into layers that are parallel to (001) (Fig. 2).

There is no heavy atom with a significant anomalous dispersion contribution, so the absolute configuration from the diffraction pattern itself could not be determined. However, the absolute configuration of the eucomic acid has been established by synthesis (Heller & Tamm, 1974) though its crystal structure has not been determined. Therefore the title compound is expected to share the same R configuration at the chiral centre C8.

Experimental

The title compound was purified from the stems of Opuntia vulgaris according to the reported procedures (Jiang et al., 2002). Briefly, the stems of Opuntia vulgaris (1 kg) was extracted with 95% ethanol under room temperature. The extracted solution was concentrated with rotary evaporator to afford a crude extract, which was suspended in distilled water and partitioned with petroleum ether, ethyl acetate and n-butanol. Then the n-butanol fraction was subjected to silica gel column chromatography eluted with methanol-chloroform gradient solvent system to afford the title compound (16 mg). The transparent rectangular crystals of the title compound with average size of 0.50 × 0.40 × 0.30 mm were obtained by slow evaporation of the methanol solution at room temperature.