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X-ray powder diffraction data for monomenthyl succinate, C14H24O4

Published online by Cambridge University Press:  26 July 2016

Xiaoxiang Liao ,
Dalin Yuan ,
Ying Fan ,
Hongqin Yang ,
Yanmei Huang ,
Ji Yang ,
Wei Zhao ,
Hui Li  and
Jianguo Tang
Xiaoxiang Liao
Affiliation:
Technology Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650204, Yunnan, China College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, China
Dalin Yuan
Affiliation:
Technology Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650204, Yunnan, China
Ying Fan
Affiliation:
Technology Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650204, Yunnan, China
Hongqin Yang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, China
Yanmei Huang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, China
Ji Yang
Affiliation:
Technology Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650204, Yunnan, China
Wei Zhao
Affiliation:
Technology Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650204, Yunnan, China
Hui Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, China
Jianguo Tang*
Affiliation:
Technology Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650204, Yunnan, China
*
a) Author to whom correspondence should be addressed. Electronic mail: jgtang@163.com

Abstract

X-ray powder diffraction data, unit-cell parameters, and space group for monomenthyl succinate, C14H24O4, are reported [a = 19.352(2), b = 30.015(1), c = 5.277(0) Å, α = β = γ = 90°, unit-cell volume V = 3065.1(6) Å3, Z = 8, and space group Pba2]. All measured lines were indexed and are consistent with the Pba2 space group. No detectable impurities were observed.

Keywords

X-ray powder diffraction datamonomenthyl succinate

Information

Type
Data Reports
Information
Powder Diffraction , Volume 31 , Issue 4 , December 2016 , pp. 301 - 303
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Copyright
Copyright © International Centre for Diffraction Data 2016 

I. INTRODUCTION

Monomenthyl succinate, C14H24O4 (Figure 1), systematic name 4-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy-4-oxobutanoic acid, is essentially tasteless and provides a good balance of cooling onset and length of cooling (Erman, Reference Erman2007). The CAS register number of the compound is 77341-67-4. Monomenthyl succinate is a safe and innocuous additive of mint, so it is widely used in food products, and it has FEMA (Flavor and Extract Manufacture's Association) GRAS (generally recognized as safe) status (Marin and Schippa, Reference Marin and Schippa2006).

Figure 1.

Structural formula of monomenthyl succinate.

Presently, the crystal structure of monomenthyl succinate by single-crystal diffraction or powder diffraction has not been reported in the literature.

II. EXPERIMENTAL

A. Sample preparation

The title compound (purity: 98%) was purchased from J&K Chemical Co., Ltd. (Beijing, China). It was ground into powder (ρ = 1.06 g cm−3, T melt = 61–63 °C), sieved through a 300-mesh screen, and then mounted on a flat zero background plate. The structure of the compound was characterized by the Fourier transform infrared spectroscopy (FTIR) (Figure S1) and elemental analysis. The elemental analysis showed that the content of C, H, and O were 65.75, 10.39, and 23.86, respectively. The measured FTIR spectrum is consistent with the presumed structure of monomenthyl succinate (Figure 1).

B. Diffraction data collection and reduction

The diffraction pattern for the title compound was collected by an X'Pert PRO diffractometer (PANalytical Co., Ltd., Netherlands) with an X'celerator detector and CuKα 1 radiation (λ = 1.54056 Å, generator setting: 40 kV and 40 mA). The diffractometer was operated in the angular range from 4° to 50°2θ with a step size of 0.01313°2θ and a counting time of 30 ms step−1. The measurement was performed at room temperature and a controlled relative humidity level of 60%. Data evaluation was performed using the Reflex module in the software package Material Studio 4.2 (Accelrys Co., Ltd., USA), which we used to successfully solve the organic crystal structures such as norandrostenedione (Tang et al., Reference Tang, Wu, Pan, Zhang, Cheng and Li2013), levetiracetam (Xu et al., Reference Xu, Liang, Wu, Zhang, Tang and Li2013), and meloxicam (Wu et al., Reference Wu, Tang, Li, Zhang and Li2014).

Automatic indexing was carried out using peak positions obtained from the powder diffraction profiles by the X-Cell method (Neumann, Reference Neumann2003). Then the best indexing results 414 for the value of figure of merit were refined using the Pawley method (Pan et al., Reference Pan, Guo, Duan, Cheng and Li2012) resulting in final R wp of the structure was converged at 8.56%.

III. RESULTS

The calculated density is 1.05 g cm−3, which coincides well with the experimental result (1.06 g cm−3). Besides, the elemental compositions calculated for monomenthyl succinate are C: 65.63, H: 9.38, and O: 24.99%, respectively, which are in good agreement with the experimental values and confirmed the high purity.

The experimental X-ray powder diffraction (XRD) pattern is depicted in Figure 2. Indexing results confirmed that monomenthyl succinate is orthorhombic with space group Pba2, and unit-cell parameters after Pawley refinement are a = 19.352(2), b = 30.015(1), c = 5.277(0) Å, α = β = γ = 90°, unit-cell volume V = 3065.1(6) Å3, and Z = 8. Table I gives the 2θ, d-spacing, relative intensity, and hkl for each observed line. All lines were indexed and are consistent with the Pba2 space group.

Figure 2.

X-ray powder diffraction pattern of monomenthyl succinate, using CuKα1 radiation (λ = 1.54056 Å).

Table I.

XRD data of monomenthyl succinate.

All measured lines were indexed and are consistent with the Pba2 space group. The d-values were calculated using CuKα 1 radiation (λ = 1.54056 Å).

SUPPLEMENTARY MATERIAL

The supplementary material for this article can be found at http://dx.doi.org/10.1017/S0885715616000427

ACKNOWLEDGEMENT

We gratefully acknowledge the financial support from China Tobacco Yunnan Industrial Co., Ltd. (Grant No. 2014H1069).

References

Erman, M. (2007). “New developments in physiological cooling agents,” Perfumer Flavorist. 32(10), 20–35.Google Scholar
Marin, C., Schippa, C. (2006). “Identification of monomenthyl succinate in natural mint extracts by LC–ESI–MS–MS and GC–MS,” J. Agric. Food Chem. 54(13), 4814–4819.Google Scholar
Neumann, M. A. (2003). “X-Cell: a novel indexing algorithm for routine tasks and difficult cases,” J. Appl. Crystallogr. 36, 356–365.Google Scholar
Pan, Q. P., Guo, J., Duan, Q., Cheng, Q., and Li, H. (2012). “Comparative crystal structure determination of griseofulvin: powder X-ray diffraction versus single-crystal X-ray diffraction,” Chin. Sci. Bull. 57, 3867–3871.Google Scholar
Tang, P. X., Wu, X. Q., Pan, Q. Q., Zhang, L. L., Cheng, Q., and Li, H. (2013). “X-ray powder diffraction data for norandrostenedione,” Powder Diffr. 28(4), 302–304.Google Scholar
Wu, X. Q., Tang, P. X., Li, S. S., Zhang, L. L., and Li, H. (2014). “X-ray powder diffraction data for meloxicam, C14H13N3O4S2 ,” Powder Diffr. 29, 196–198.Google Scholar
Xu, K. L., Liang, B., Wu, X. Q., Zhang, L. L., Tang, P. X., and Li, H. (2013). “X-ray powder diffraction data for levetiracetam,” Powder Diffr. 29(1), 51–52.Google Scholar
Figure 0

Figure 1. Structural formula of monomenthyl succinate.

Figure 1

Figure 2. X-ray powder diffraction pattern of monomenthyl succinate, using CuKα1 radiation (λ = 1.54056 Å).

Figure 2

Table I. XRD data of monomenthyl succinate.

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