3-Eth­oxy-4-hydroxy­benzaldehyde

Yong Li; Xinxi Zhang; Jun Zheng; Xiaoling Wang

doi:10.1107/S1600536808030419

. 2008 Sep 24;64(Pt 10):o2008. doi: 10.1107/S1600536808030419

3-Ethoxy-4-hydroxybenzaldehyde

Yong Li ^a,^*, Xinxi Zhang ^a, Jun Zheng ^a, Xiaoling Wang ^b

PMCID: PMC2959403 PMID: 21201206

Abstract

The title compound (ethyl vanillin), C₉H₁₀O₃, an important food additive and flavouring agent approved by FAO/WHO, has a vanilla odor four times that of vanillin and shows antimutagenic activity. There are two molecules in the asymmetric unit, each having a planar conformation and an intramolecular O—H⋯O bond. Molecules are connected side-by-side, building infinite ribbons along c via intermolecular O—H⋯O hydrogen bonds between the carbonyl and hydroxyl groups. The ribbons are then packed into layers perpendicular to the a axis.

Related literature

For anti-mutagenic activity, see: Ohta et al. (1986 ▶). For the synthetic method, see: Gradeff & Murayama (1982 ▶). For related literature, see: Li (2008 ▶).

Experimental

Crystal data

C₉H₁₀O₃
M _r = 166.17
Monoclinic,
a = 13.7352 (6) Å
b = 14.4140 (6) Å
c = 8.7890 (4) Å
β = 100.742 (3)°
V = 1709.55 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.50 × 0.50 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
16625 measured reflections
3934 independent reflections
2581 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.155
S = 1.01
3934 reflections
297 parameters
All H-atom parameters refined
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030419/dn2380sup1.cif

e-64-o2008-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030419/dn2380Isup2.hkl

e-64-o2008-Isup2.hkl^{(192.8KB, 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
O2—H1⋯O1ⁱ	0.79 (3)	2.03 (3)	2.6951 (17)	142 (3)
O2—H1⋯O3	0.79 (3)	2.26 (3)	2.6619 (16)	112 (2)
O12—H14⋯O11ⁱⁱ	0.81 (3)	2.02 (3)	2.7117 (19)	143 (3)
O12—H14⋯O13	0.81 (3)	2.26 (3)	2.6554 (18)	111 (2)

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

Acknowledgments

The authors thank Professor Tao Zeng for invaluable advice.

supplementary crystallographic information

Comment

The title compound, an ethyl analogue of vanillin, is an important food additive and flavouring agent approved by FAO/WHO. Its vanilla odor is four times stronger than the flavour of vanillin. Now, it is widely used in food, beverage, cigarette and cosmetics. This synthetic compound was reported to show marked anti-mutagenic activity against mutagenicity induced by 4-nitroquinoline-1-oxide, furylfuramide, captan or methylglyoxal, similar to another report (Li, 2008). It was assumed that the anti-mutagenic activity was due to enhancement of an error-free recombinational repair system (Ohta et al., 1986). But the structure of ethyl vanillin has never been reported. we then report herein its crystal structure determination (Fig.1). The crystal structure consists of layers of planar molecules linked as one-dimensional chains (Fig. 2).

Experimental

One of the synthetic methods was reported by literature(Gradeff & Murayama, 1982). The crude title compound commercially available was recrystallized two times from EtOH/water (1:1) solution, and then colourless block crystals were collected after slow evaporation at room temperature.