Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C6H6O7, garcinia lactone [systematic name: (2S,3S)-3-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­furan-2,3-dicarboxylic acid] was isolated from the rind of Garcinia cambogia. The five-membered ring adopts an envelope conformation and the packing is stabilized by O—H...O and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703838X/hb2498sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703838X/hb2498Isup2.hkl
Contains datablock I

CCDC reference: 662415

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.066
  • Data-to-parameter ratio = 7.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.08 PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C6 .. 3.00 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.66 From the CIF: _reflns_number_total 836 Count of symmetry unique reflns 836 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The main active ingredient of Garcinia cambogia fruit rind is (-)hydroxycitric acid (HCA) along with Garcinia lactone and citric acid (Clouatre & Robenbaum, 1994). In India the fruit is known as kokum, the extract of which is used as a souring agent in cooking. In Indian medicine, Garcinia is considered to be one of the prime herbs that is beneficial for heart. Garcinia has also received worldwide attention as a nutraceutical for effective obesity control (Sullivan et al., 1974; Clouatre & Robenbaum, 1994). The title compound, (I), (Fig. 1) was extracted by a novel procedure (Balasubramanyam et al.,2000).

The five membered C1/C2/C3/C4/O2 lactone ring in (I) adopts an envelope conformation with C3 deviating by 0.539 (1) Å from the plane of the other four atoms. Selected torsion angles for O2/C4/C5/C6 and C2/C3/C6/O5 are -20.88 (1)° and -154.45 (1)°, respectively.

The crystal structure of (I) is stabilized by intermolecular O—H···O and intra- and intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature top

For background literature, see: Sullivan et al. (1974); Clouatre & Robenbaum (1994). For the extraction procedure, see: Balasubramanyam et al., (2000).

Experimental top

Crushed and dried Garcinia cambogia fruit rinds (200 g) were immersed in 250 ml hot water for 10 h. Water was decanted and the process was repeated three times. The combined water extracts were concentrated to get a thick syrupy mass to which acetone was added. The precipitated mass was filtered off and washed with acetone. On evaporation, the acetone layer gave a gummy mass which was extracted with ethyl acetate. The ethyl acetate was charcolized, dried over anhydrous sodium sulfate, which on concentration gave crude garcinia lactone. This material was recrystallized using ethyl acetate and n-hexane to yield the title compound (29.0 g) in high purity. Colourless plates of (I) were grown from ethyl acetate and n-hexane (1:1 v/v) for data collection.

Refinement top

In the absence of significant anomalous dispersion effects, Friedel pairs were merged. Therefore the absolute structure of (I) is indeterminate from this experiment (in the arbitrarily chosen model used here, C3 and C4 have S conformation). All the H atoms were positioned geometrically (C—H = 0.97–0.98 Å, O—H = 0.82 Å) and refined as riding, with Uiso(H) = 1.5Ueq(C) or 1.5Ueq(O).

Structure description top

The main active ingredient of Garcinia cambogia fruit rind is (-)hydroxycitric acid (HCA) along with Garcinia lactone and citric acid (Clouatre & Robenbaum, 1994). In India the fruit is known as kokum, the extract of which is used as a souring agent in cooking. In Indian medicine, Garcinia is considered to be one of the prime herbs that is beneficial for heart. Garcinia has also received worldwide attention as a nutraceutical for effective obesity control (Sullivan et al., 1974; Clouatre & Robenbaum, 1994). The title compound, (I), (Fig. 1) was extracted by a novel procedure (Balasubramanyam et al.,2000).

The five membered C1/C2/C3/C4/O2 lactone ring in (I) adopts an envelope conformation with C3 deviating by 0.539 (1) Å from the plane of the other four atoms. Selected torsion angles for O2/C4/C5/C6 and C2/C3/C6/O5 are -20.88 (1)° and -154.45 (1)°, respectively.

The crystal structure of (I) is stabilized by intermolecular O—H···O and intra- and intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2).

For background literature, see: Sullivan et al. (1974); Clouatre & Robenbaum (1994). For the extraction procedure, see: Balasubramanyam et al., (2000).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. View of (I) with 30% probability displacement ellipsoids (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. Molecular chains along a axis in (I) due to O—H···O hydrogen bonds and C—H···O interactions (dashed lines).
(2S,3S)-3-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylic acid top
Crystal data top
C6H6O7Dx = 1.723 Mg m3
Mr = 190.11Melting point = 449–451 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 545 reflections
a = 6.2657 (10) Åθ = 1.0–28.0°
b = 8.6591 (14) ŵ = 0.16 mm1
c = 13.504 (2) ÅT = 292 K
V = 732.7 (2) Å3Plate, colourless
Z = 40.30 × 0.20 × 0.10 mm
F(000) = 392
Data collection top
Bruker SMART APEX CCD
diffractometer
836 independent reflections
Radiation source: fine-focus sealed tube810 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.7°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.935, Tmax = 0.984k = 1010
5568 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0319P)2 + 0.2219P]
where P = (Fo2 + 2Fc2)/3
836 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C6H6O7V = 732.7 (2) Å3
Mr = 190.11Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.2657 (10) ŵ = 0.16 mm1
b = 8.6591 (14) ÅT = 292 K
c = 13.504 (2) Å0.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
836 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
810 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.984Rint = 0.022
5568 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 1.10Δρmax = 0.21 e Å3
836 reflectionsΔρmin = 0.17 e Å3
118 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O51.0046 (2)0.15092 (19)0.14395 (13)0.0390 (4)
O60.4251 (2)0.00593 (19)0.05515 (12)0.0350 (4)
O30.7966 (2)0.09450 (18)0.23129 (10)0.0281 (4)
H30.91720.11690.21260.042*
O20.4978 (2)0.21068 (16)0.08633 (10)0.0259 (3)
O70.7760 (3)0.03680 (19)0.07537 (11)0.0336 (4)
H70.73770.08400.12490.050*
O40.6882 (2)0.25433 (17)0.10495 (12)0.0339 (4)
H40.75920.33210.09420.051*
O10.1911 (2)0.19661 (19)0.16734 (13)0.0371 (4)
C60.8148 (3)0.1423 (2)0.13577 (15)0.0254 (5)
C20.4591 (3)0.0075 (2)0.18784 (15)0.0250 (5)
H2A0.39310.09720.15760.030*
H2B0.44510.01490.25920.030*
C10.3614 (3)0.1399 (2)0.14948 (15)0.0252 (4)
C30.6927 (3)0.0069 (2)0.15732 (14)0.0213 (4)
C40.6711 (3)0.1092 (2)0.06284 (14)0.0216 (4)
H4A0.80230.16810.05150.026*
C50.6089 (3)0.0196 (2)0.03010 (14)0.0243 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0218 (8)0.0381 (9)0.0570 (10)0.0038 (7)0.0013 (8)0.0039 (9)
O60.0283 (9)0.0377 (9)0.0389 (9)0.0021 (8)0.0084 (7)0.0072 (7)
O30.0240 (7)0.0391 (9)0.0212 (7)0.0047 (7)0.0007 (6)0.0034 (6)
O20.0271 (8)0.0240 (7)0.0265 (7)0.0046 (6)0.0039 (7)0.0023 (6)
O70.0336 (9)0.0420 (9)0.0253 (7)0.0052 (7)0.0015 (7)0.0095 (7)
O40.0287 (8)0.0251 (7)0.0480 (10)0.0020 (7)0.0003 (7)0.0072 (7)
O10.0246 (8)0.0359 (9)0.0510 (10)0.0055 (8)0.0084 (8)0.0037 (8)
C60.0244 (10)0.0287 (11)0.0230 (10)0.0010 (9)0.0000 (9)0.0061 (9)
C20.0221 (10)0.0274 (10)0.0254 (10)0.0003 (9)0.0036 (8)0.0016 (9)
C10.0228 (10)0.0264 (10)0.0263 (10)0.0015 (9)0.0008 (9)0.0039 (9)
C30.0207 (10)0.0260 (10)0.0173 (9)0.0030 (10)0.0003 (8)0.0010 (8)
C40.0199 (9)0.0239 (9)0.0209 (10)0.0009 (9)0.0016 (8)0.0006 (8)
C50.0279 (11)0.0233 (10)0.0215 (10)0.0005 (9)0.0002 (8)0.0019 (8)
Geometric parameters (Å, º) top
O5—C61.197 (2)O1—C11.199 (3)
O6—C51.206 (3)C6—C31.530 (3)
O3—C31.413 (2)C2—C11.507 (3)
O3—H30.8200C2—C31.526 (3)
O2—C11.354 (2)C2—H2A0.9700
O2—C41.433 (2)C2—H2B0.9700
O7—C51.307 (3)C3—C41.559 (3)
O7—H70.8200C4—C51.526 (3)
O4—C61.320 (3)C4—H4A0.9800
O4—H40.8200
C3—O3—H3109.5O3—C3—C2107.16 (16)
C1—O2—C4109.88 (15)O3—C3—C6110.94 (16)
C5—O7—H7109.5C2—C3—C6117.51 (17)
C6—O4—H4109.5O3—C3—C4108.30 (16)
O5—C6—O4125.5 (2)C2—C3—C4100.64 (15)
O5—C6—C3122.1 (2)C6—C3—C4111.56 (15)
O4—C6—C3112.34 (16)O2—C4—C5107.47 (15)
C1—C2—C3103.13 (17)O2—C4—C3103.47 (15)
C1—C2—H2A111.1C5—C4—C3114.01 (16)
C3—C2—H2A111.1O2—C4—H4A110.5
C1—C2—H2B111.1C5—C4—H4A110.5
C3—C2—H2B111.1C3—C4—H4A110.5
H2A—C2—H2B109.1O6—C5—O7126.6 (2)
O1—C1—O2120.2 (2)O6—C5—C4121.64 (18)
O1—C1—C2129.7 (2)O7—C5—C4111.72 (18)
O2—C1—C2110.10 (17)
C4—O2—C1—O1169.51 (18)C1—O2—C4—C591.59 (18)
C4—O2—C1—C210.6 (2)C1—O2—C4—C329.35 (19)
C3—C2—C1—O1166.8 (2)O3—C3—C4—O276.88 (18)
C3—C2—C1—O213.1 (2)C2—C3—C4—O235.34 (19)
C1—C2—C3—O384.37 (18)C6—C3—C4—O2160.76 (15)
C1—C2—C3—C6150.01 (17)O3—C3—C4—C5166.72 (15)
C1—C2—C3—C428.73 (19)C2—C3—C4—C581.1 (2)
O5—C6—C3—O330.7 (3)C6—C3—C4—C544.4 (2)
O4—C6—C3—O3151.34 (16)O2—C4—C5—O620.9 (3)
O5—C6—C3—C2154.5 (2)C3—C4—C5—O693.2 (2)
O4—C6—C3—C227.6 (2)O2—C4—C5—O7159.30 (16)
O5—C6—C3—C490.1 (3)C3—C4—C5—O786.7 (2)
O4—C6—C3—C487.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.821.952.764 (2)173
O4—H4···O6ii0.821.902.721 (2)174
O7—H7···O3iii0.821.962.697 (2)150
C4—H4A···O2iv0.982.463.268 (2)139
C2—H2A···O40.972.402.808 (3)104
C2—H2A···O5v0.972.493.163 (2)127
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y1/2, z; (iii) x+3/2, y, z1/2; (iv) x+1/2, y+1/2, z; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC6H6O7
Mr190.11
Crystal system, space groupOrthorhombic, P212121
Temperature (K)292
a, b, c (Å)6.2657 (10), 8.6591 (14), 13.504 (2)
V3)732.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.935, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
5568, 836, 810
Rint0.022
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.066, 1.10
No. of reflections836
No. of parameters118
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.17

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXTL (Bruker, 2000), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.821.952.764 (2)173
O4—H4···O6ii0.821.902.721 (2)174
O7—H7···O3iii0.821.962.697 (2)150
C4—H4A···O2iv0.982.463.268 (2)139
C2—H2A···O40.972.402.808 (3)104
C2—H2A···O5v0.972.493.163 (2)127
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y1/2, z; (iii) x+3/2, y, z1/2; (iv) x+1/2, y+1/2, z; (v) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds