(E)-2-Hy­droxy-4-meth­oxy-3-(3-methyl­but-2-en­yl)-6-styryl­benzoic acid

Ji, X.; Jin, J.; Zheng, G.; Li, Z.

doi:10.1107/S1600536812050258

Volume 69
Part 1
Page o91
January 2013

Received 28 November 2012
Accepted 10 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.052
wR = 0.152
Data-to-parameter ratio = 13.7
Details

(E)-2-Hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-styrylbenzoic acid

Xingyue Ji,^a Jie Jin,^a Guanghui Zheng ^a and Zhuorong Li ^a ^*

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China
Correspondence e-mail: l-z-r@263.net

The title compound, C₂₁H₂₂O₄, also known as cajanine, features an intramolecular O-HO hydrogen bond between the adjacent carboxy and hydroxy groups. The benzene rings make an interplanar angle of 175.4 (2)°. In the crystal, molecules are linked by pairs of O-HO hydrogen bonds, forming inversion dimers.

Related literature

Cajanine is an important component of the herb Cajanus cajan L., which is used in traditional Chinese medicine to treat osteonecrosis of the femoral head. For the total synthesis of cajanine, see: Ji et al. (2011). For the bioactivity of cajanine, see: Fu et al. (2009); Ji et al. (2011); Luo et al. (2008a,b); Zheng et al. (2007a,b); Inman & Hopp (2002); Ruan et al. (2009).

Experimental

Crystal data

C₂₁H₂₂O₄
M_r = 338.39
Triclinic, $[P \overline 1]$
a = 6.9790 (3) Å
b = 9.9975 (8) Å
c = 13.8202 (11) Å
= 77.899 (1)°
= 78.956 (2)°
= 78.507 (2)°
V = 912.58 (11) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 298 K
0.35 × 0.32 × 0.31 mm

Data collection

Bruker SMART APEX diffractometer
4547 measured reflections
3138 independent reflections
1735 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.152
S = 1.06
3138 reflections
229 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.85	2.667 (2)	176
O3-H3O2	0.82	1.82	2.546 (2)	147
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5309 ).

Acknowledgements

This work was supported by the National S&T Major Special Project on Major New Drug Innovation (2012ZX09301002-001). We also thank Professor Su-na Wang at Liaocheng University for assistance with the crystallography and help with the X-ray experiment.

References

Bruker (1999). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Fu, Y.-J., Zhu, Y.-G., Wu, N., Kong, Y., Liu, W. & Hua, X. (2009). Chin. Patent CN 101485649.
Inman, W. D. & Hopp, D. C. (2002). US Patent 20020058701A1.
Ji, X.-Y., Xue, S.-T., Zheng, G.-H., Han, Y.-X., Liu, Z.-Y., Jiang, J.-D. & Li, Z.-R. (2011). Acta. Pharm. Sin. B, 1, 93-99.
Luo, Q.-F., Sun, L., Si, J.-Y. & Chen, D.-H. (2008a). Phytomedicine, 15, 932-939.
Luo, Q.-F., Sun, L., Si, J.-Y., Chen, D.-H. & Du, G.-H. (2008b). Yao Xue Xue Bao, 43, 145-149.
Ruan, C.-J., Si, J.-Y., Zhang, L., Chen, D.-H., Du, G.-H. & Sun, L. (2009). Neurosci. Lett. 467, 159-63.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zheng, Y.-Y., Yang, J., Chen, D.-H. & Sun, L. (2007a). Yao Xue Xue Bao, 42, 386-391.
Zheng, Y.-Y., Yang, J., Chen, D.-H. & Sun, L. (2007b). Yao Xue Xue Bao, 42, 562-565.

organic compounds