2-[(1R*,4R*)-1,4-Dihydroxycyclohexyl]acetic acid

The title compound, C8H14O4, is an isolation product of the aerial parts of Senecio desfontanei. The acetic acid group is oriented at a dihedral angle of 48.03 (9)° with respect to the basal plane of the cyclohexane-1,4-diol chair. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring with an envelope conformation. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, resulting in R 3 3(20) ring motifs and C(2) O—H⋯O—H⋯O—H⋯ chains. Overall, a three-dimensional polymeric network arises. A C—H⋯O contact is also present.

The title compound, C 8 H 14 O 4 , is an isolation product of the aerial parts of Senecio desfontanei. The acetic acid group is oriented at a dihedral angle of 48.03 (9) with respect to the basal plane of the cyclohexane-1,4-diol chair. An intramolecular O-HÁ Á ÁO hydrogen bond generates an S(6) ring with an envelope conformation. In the crystal, molecules are linked by O-HÁ Á ÁO hydrogen bonds, resulting in R 3 3 (20) ring motifs and C(2) O-HÁ Á ÁO-HÁ Á ÁO-HÁ Á Á chains. Overall, a three-dimensional polymeric network arises. A C-HÁ Á ÁO contact is also present.
SHH and JR acknowledge financial support by the Higher Education Commission, Pakistan, under its Indigenous 5000 PhD scheme.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5819).

Experimental
The air dried and pulverized aerial parts of Senecio desfontanei (12 kg), collected from Kaghan, KPK, Pakistan, in July 2008, were subjected to cold extraction with methanol (MeOH) in percolator. The MeOH extract was concentrated in vacuo to give dark greenish crude extract (300 g) which was then suspended in distilled water and successively partitioned with n-hexane, dichloromethane (DCM), ethyl acetate (EtOAc). The EtOAc fraction (90 g) was subjected to column chromatography (CC) on silica gel and n-hexane: EtOAc (100:0 → 0:100) as eluting system. This resulted in total of 20 subfractions i.e. 1 A-20 A compiled on the basis of TLC profiles. Subfraction 12 A was resubjected to CC on silica gel and eluted with n-hexane: EtOAc (20:80) yielding a crystalline compound containing minor impurities. The impurity was washed off with DCM.
Transparent needles of the title compound were obtained by recrystallization using a mixture of EtOAc:MeOH (85:15).

Refinement
In the absence of significant anomolous scattering, the Friedal pairs were merged before refinement.