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The title compound {systematic name: 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol, commonly named glabridin}, C20H20O4, is a species-specific biomarker from the roots Glycyrrhiza glabra L. (European licorice, Fabaceae). In the present study, this prenylated isoflavan has been purified from an enriched CHCl3 fraction of the extract of the root, using three steps of medium-pressure liquid chromatography (MPLC) by employing HW-40F, Sephadex LH-20 and LiChroCN as adsorbents. Pure glabridin was crystallized from an MeOH-H2O mixture (95:5 v/v) to yield colorless crystals containing one molecule per asymmetric unit (Z' = 1) in the space group P212121. Although the crystal structure has been reported before, the determination of the absolute configuration remained uncertain. Stereochemical analysis, including circular dichroism, NMR data and an X-ray diffraction data set with Bijvoet differences, confirms that glabridin, purified from its natural source, is found only in a C3 R configuration. These results can therefore be used as a reference for the assignment of the configuration and enantiopurity of any isolated or synthetic glabridin sample.
Supporting information
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).
4-[(3
R)-8,8-Dimethyl-3,4-dihydro-2
H-pyrano[2,3-
f]chromen-3-yl]benzene-1,3-diol
top
Crystal data top
C20H20O4 | Dx = 1.343 Mg m−3 |
Mr = 324.36 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 9904 reflections |
a = 6.3744 (10) Å | θ = 4.2–68.6° |
b = 11.961 (2) Å | µ = 0.76 mm−1 |
c = 21.041 (3) Å | T = 92 K |
V = 1604.3 (4) Å3 | Needle, colourless |
Z = 4 | 0.15 × 0.05 × 0.03 mm |
F(000) = 688 | |
Data collection top
Bruker Kappa APEXII DUO CCD aea-detector diffractometer | 2708 reflections with I > 2σ(I) |
Radiation source: IµS microfocus | Rint = 0.046 |
φ and ω scans | θmax = 68.5°, θmin = 4.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −7→7 |
Tmin = 0.895, Tmax = 0.978 | k = 0→14 |
47918 measured reflections | l = 0→24 |
2879 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | Only H-atom coordinates refined |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0324P)2 + 0.3419P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2879 reflections | Δρmax = 0.13 e Å−3 |
277 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Absolute structure: Flack x parameter determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (6) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1A | 0.5348 (3) | 0.41798 (14) | 0.46350 (8) | 0.0178 (4) | |
C2A | 0.3549 (3) | 0.34964 (15) | 0.46223 (8) | 0.0179 (4) | |
O2A | 0.2046 (2) | 0.37100 (11) | 0.50754 (6) | 0.0235 (3) | |
H2A | 0.119 (4) | 0.317 (2) | 0.5091 (11) | 0.035* | |
C3A | 0.3301 (3) | 0.26477 (15) | 0.41751 (9) | 0.0183 (4) | |
H3A | 0.209 (4) | 0.2201 (17) | 0.4177 (9) | 0.022* | |
C4A | 0.4854 (3) | 0.24727 (15) | 0.37179 (8) | 0.0189 (4) | |
O4A | 0.4515 (2) | 0.16339 (11) | 0.32871 (6) | 0.0243 (3) | |
H4A | 0.550 (4) | 0.161 (2) | 0.3009 (11) | 0.036* | |
C5A | 0.6645 (3) | 0.31343 (16) | 0.37152 (9) | 0.0211 (4) | |
H5A | 0.774 (4) | 0.3022 (18) | 0.3398 (9) | 0.025* | |
C6A | 0.6871 (3) | 0.39709 (15) | 0.41730 (9) | 0.0203 (4) | |
H6A | 0.814 (4) | 0.4403 (17) | 0.4177 (10) | 0.024* | |
O1 | 0.4235 (2) | 0.69199 (10) | 0.54946 (6) | 0.0214 (3) | |
C2 | 0.4297 (3) | 0.61178 (16) | 0.49751 (9) | 0.0203 (4) | |
H21 | 0.487 (4) | 0.6480 (17) | 0.4591 (10) | 0.024* | |
H22 | 0.280 (4) | 0.5939 (18) | 0.4886 (10) | 0.024* | |
C3 | 0.5547 (3) | 0.50714 (15) | 0.51435 (8) | 0.0182 (4) | |
H3 | 0.493 (3) | 0.4770 (17) | 0.5531 (10) | 0.022* | |
C4 | 0.7802 (3) | 0.54459 (15) | 0.52873 (9) | 0.0205 (4) | |
H41 | 0.865 (3) | 0.4797 (19) | 0.5424 (10) | 0.025* | |
H42 | 0.838 (3) | 0.5780 (18) | 0.4902 (10) | 0.025* | |
C5 | 0.9300 (3) | 0.63739 (16) | 0.62720 (9) | 0.0217 (4) | |
H5 | 1.051 (4) | 0.5890 (18) | 0.6218 (9) | 0.026* | |
C6 | 0.9161 (3) | 0.70976 (16) | 0.67885 (9) | 0.0217 (4) | |
H6 | 1.029 (4) | 0.7158 (18) | 0.7106 (9) | 0.026* | |
C7 | 0.7389 (3) | 0.77578 (14) | 0.68483 (8) | 0.0180 (4) | |
C8 | 0.5746 (3) | 0.77139 (15) | 0.64067 (8) | 0.0177 (4) | |
C9 | 0.5938 (3) | 0.69660 (15) | 0.58945 (8) | 0.0176 (4) | |
C10 | 0.7716 (3) | 0.62927 (14) | 0.58174 (8) | 0.0183 (4) | |
O1B | 0.7192 (2) | 0.84092 (10) | 0.73914 (6) | 0.0208 (3) | |
C2B | 0.5885 (3) | 0.94209 (15) | 0.73530 (9) | 0.0205 (4) | |
C3B | 0.3909 (3) | 0.91720 (16) | 0.69821 (9) | 0.0219 (4) | |
H3B | 0.269 (4) | 0.9652 (18) | 0.7094 (10) | 0.026* | |
C4B | 0.3886 (3) | 0.83923 (16) | 0.65271 (8) | 0.0204 (4) | |
H4B | 0.264 (4) | 0.8230 (17) | 0.6288 (10) | 0.024* | |
C5B | 0.5396 (3) | 0.97127 (19) | 0.80411 (9) | 0.0266 (4) | |
H51B | 0.455 (4) | 1.043 (2) | 0.8066 (11) | 0.040* | |
H52B | 0.672 (4) | 0.982 (2) | 0.8270 (11) | 0.040* | |
H53B | 0.451 (4) | 0.914 (2) | 0.8248 (11) | 0.040* | |
C6B | 0.7177 (4) | 1.03343 (17) | 0.70313 (10) | 0.0289 (5) | |
H61B | 0.756 (4) | 1.010 (2) | 0.6609 (12) | 0.043* | |
H62B | 0.849 (4) | 1.049 (2) | 0.7261 (12) | 0.043* | |
H63B | 0.631 (4) | 1.107 (2) | 0.7017 (11) | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0214 (9) | 0.0164 (8) | 0.0156 (9) | 0.0009 (8) | −0.0006 (8) | 0.0026 (7) |
C2A | 0.0188 (9) | 0.0191 (9) | 0.0159 (9) | 0.0031 (7) | 0.0031 (7) | 0.0042 (7) |
O2A | 0.0217 (7) | 0.0227 (7) | 0.0262 (7) | −0.0035 (6) | 0.0081 (6) | −0.0026 (5) |
C3A | 0.0187 (9) | 0.0162 (8) | 0.0201 (9) | −0.0009 (7) | −0.0010 (8) | 0.0025 (7) |
C4A | 0.0239 (10) | 0.0167 (9) | 0.0160 (9) | 0.0016 (8) | −0.0021 (7) | 0.0007 (7) |
O4A | 0.0280 (7) | 0.0241 (7) | 0.0207 (7) | −0.0048 (6) | 0.0051 (6) | −0.0061 (5) |
C5A | 0.0231 (10) | 0.0221 (9) | 0.0181 (9) | 0.0010 (8) | 0.0037 (8) | 0.0007 (7) |
C6A | 0.0211 (9) | 0.0196 (9) | 0.0202 (9) | −0.0021 (8) | 0.0015 (8) | 0.0015 (7) |
O1 | 0.0215 (7) | 0.0226 (7) | 0.0201 (6) | 0.0047 (6) | −0.0051 (6) | −0.0058 (5) |
C2 | 0.0244 (10) | 0.0211 (9) | 0.0155 (9) | 0.0023 (8) | −0.0016 (8) | −0.0038 (7) |
C3 | 0.0201 (9) | 0.0191 (9) | 0.0154 (9) | 0.0002 (7) | 0.0018 (7) | 0.0003 (7) |
C4 | 0.0203 (9) | 0.0200 (9) | 0.0214 (9) | 0.0014 (8) | 0.0013 (8) | −0.0006 (8) |
C5 | 0.0193 (9) | 0.0200 (9) | 0.0258 (10) | 0.0010 (8) | −0.0008 (8) | 0.0000 (8) |
C6 | 0.0207 (9) | 0.0226 (10) | 0.0219 (10) | −0.0008 (8) | −0.0047 (8) | 0.0007 (7) |
C7 | 0.0227 (9) | 0.0163 (9) | 0.0151 (9) | −0.0044 (7) | −0.0003 (7) | 0.0014 (7) |
C8 | 0.0200 (9) | 0.0164 (8) | 0.0168 (9) | −0.0022 (7) | 0.0010 (7) | 0.0034 (7) |
C9 | 0.0193 (9) | 0.0176 (8) | 0.0158 (9) | −0.0030 (7) | −0.0013 (7) | 0.0038 (7) |
C10 | 0.0187 (9) | 0.0169 (8) | 0.0193 (9) | −0.0017 (7) | 0.0022 (7) | 0.0029 (7) |
O1B | 0.0244 (7) | 0.0198 (6) | 0.0182 (6) | 0.0014 (5) | −0.0035 (5) | −0.0016 (5) |
C2B | 0.0227 (9) | 0.0182 (9) | 0.0206 (9) | 0.0022 (8) | −0.0002 (8) | −0.0003 (7) |
C3B | 0.0234 (10) | 0.0216 (10) | 0.0209 (10) | 0.0032 (8) | 0.0008 (8) | 0.0014 (8) |
C4B | 0.0202 (9) | 0.0222 (9) | 0.0188 (9) | 0.0013 (7) | −0.0015 (8) | 0.0008 (7) |
C5B | 0.0269 (11) | 0.0312 (11) | 0.0217 (10) | −0.0014 (10) | 0.0001 (9) | −0.0056 (8) |
C6B | 0.0348 (12) | 0.0217 (10) | 0.0302 (11) | −0.0034 (9) | 0.0042 (10) | 0.0010 (8) |
Geometric parameters (Å, º) top
C1A—C6A | 1.396 (3) | C5—C6 | 1.392 (3) |
C1A—C2A | 1.408 (2) | C5—C10 | 1.394 (3) |
C1A—C3 | 1.516 (2) | C5—H5 | 0.97 (2) |
C2A—O2A | 1.376 (2) | C6—C7 | 1.384 (3) |
C2A—C3A | 1.393 (3) | C6—H6 | 0.98 (2) |
O2A—H2A | 0.84 (3) | C7—O1B | 1.389 (2) |
C3A—C4A | 1.396 (3) | C7—C8 | 1.401 (3) |
C3A—H3A | 0.94 (2) | C8—C9 | 1.406 (2) |
C4A—O4A | 1.369 (2) | C8—C4B | 1.459 (3) |
C4A—C5A | 1.389 (3) | C9—C10 | 1.400 (3) |
O4A—H4A | 0.86 (3) | O1B—C2B | 1.471 (2) |
C5A—C6A | 1.396 (3) | C2B—C3B | 1.512 (3) |
C5A—H5A | 0.97 (2) | C2B—C5B | 1.521 (3) |
C6A—H6A | 0.96 (2) | C2B—C6B | 1.526 (3) |
O1—C9 | 1.375 (2) | C3B—C4B | 1.337 (3) |
O1—C2 | 1.455 (2) | C3B—H3B | 1.00 (2) |
C2—C3 | 1.525 (3) | C4B—H4B | 0.96 (2) |
C2—H21 | 0.99 (2) | C5B—H51B | 1.01 (3) |
C2—H22 | 1.00 (2) | C5B—H52B | 0.98 (3) |
C3—C4 | 1.536 (3) | C5B—H53B | 0.99 (3) |
C3—H3 | 0.97 (2) | C6B—H61B | 0.96 (3) |
C4—C10 | 1.508 (2) | C6B—H62B | 0.99 (3) |
C4—H41 | 0.99 (2) | C6B—H63B | 1.04 (3) |
C4—H42 | 0.98 (2) | | |
| | | |
C6A—C1A—C2A | 116.68 (16) | C10—C5—H5 | 116.9 (12) |
C6A—C1A—C3 | 123.98 (16) | C7—C6—C5 | 118.54 (17) |
C2A—C1A—C3 | 119.33 (16) | C7—C6—H6 | 119.5 (12) |
O2A—C2A—C3A | 121.62 (16) | C5—C6—H6 | 122.0 (12) |
O2A—C2A—C1A | 116.49 (15) | C6—C7—O1B | 117.95 (15) |
C3A—C2A—C1A | 121.89 (16) | C6—C7—C8 | 121.89 (16) |
C2A—O2A—H2A | 109.7 (16) | O1B—C7—C8 | 119.96 (16) |
C2A—C3A—C4A | 119.60 (17) | C7—C8—C9 | 117.87 (17) |
C2A—C3A—H3A | 120.3 (12) | C7—C8—C4B | 118.12 (16) |
C4A—C3A—H3A | 120.1 (12) | C9—C8—C4B | 123.89 (16) |
O4A—C4A—C5A | 122.99 (16) | O1—C9—C10 | 123.05 (16) |
O4A—C4A—C3A | 117.00 (16) | O1—C9—C8 | 115.22 (16) |
C5A—C4A—C3A | 120.01 (16) | C10—C9—C8 | 121.69 (16) |
C4A—O4A—H4A | 111.3 (17) | C5—C10—C9 | 117.82 (16) |
C4A—C5A—C6A | 119.34 (17) | C5—C10—C4 | 121.88 (16) |
C4A—C5A—H5A | 120.7 (13) | C9—C10—C4 | 120.12 (16) |
C6A—C5A—H5A | 119.9 (13) | C7—O1B—C2B | 117.87 (13) |
C5A—C6A—C1A | 122.47 (18) | O1B—C2B—C3B | 109.77 (14) |
C5A—C6A—H6A | 118.6 (13) | O1B—C2B—C5B | 104.62 (15) |
C1A—C6A—H6A | 118.9 (13) | C3B—C2B—C5B | 111.45 (16) |
C9—O1—C2 | 117.69 (14) | O1B—C2B—C6B | 107.92 (16) |
O1—C2—C3 | 112.39 (14) | C3B—C2B—C6B | 111.20 (16) |
O1—C2—H21 | 109.6 (12) | C5B—C2B—C6B | 111.62 (17) |
C3—C2—H21 | 111.0 (12) | C4B—C3B—C2B | 121.07 (17) |
O1—C2—H22 | 104.9 (12) | C4B—C3B—H3B | 124.2 (13) |
C3—C2—H22 | 111.6 (12) | C2B—C3B—H3B | 114.7 (12) |
H21—C2—H22 | 107.1 (18) | C3B—C4B—C8 | 120.24 (17) |
C1A—C3—C2 | 111.68 (14) | C3B—C4B—H4B | 121.8 (13) |
C1A—C3—C4 | 115.00 (15) | C8—C4B—H4B | 117.9 (13) |
C2—C3—C4 | 107.17 (15) | C2B—C5B—H51B | 110.6 (13) |
C1A—C3—H3 | 107.3 (12) | C2B—C5B—H52B | 108.8 (14) |
C2—C3—H3 | 106.7 (12) | H51B—C5B—H52B | 109 (2) |
C4—C3—H3 | 108.7 (12) | C2B—C5B—H53B | 112.0 (14) |
C10—C4—C3 | 107.92 (15) | H51B—C5B—H53B | 105.2 (19) |
C10—C4—H41 | 109.3 (12) | H52B—C5B—H53B | 111 (2) |
C3—C4—H41 | 109.9 (12) | C2B—C6B—H61B | 109.9 (16) |
C10—C4—H42 | 110.7 (13) | C2B—C6B—H62B | 112.3 (15) |
C3—C4—H42 | 108.1 (12) | H61B—C6B—H62B | 107 (2) |
H41—C4—H42 | 110.9 (17) | C2B—C6B—H63B | 109.4 (14) |
C6—C5—C10 | 122.20 (18) | H61B—C6B—H63B | 111 (2) |
C6—C5—H5 | 120.9 (12) | H62B—C6B—H63B | 107 (2) |
| | | |
C6A—C1A—C2A—O2A | −179.56 (15) | C6—C7—C8—C4B | 176.53 (17) |
C3—C1A—C2A—O2A | 1.4 (2) | O1B—C7—C8—C4B | 1.8 (2) |
C6A—C1A—C2A—C3A | 0.5 (2) | C2—O1—C9—C10 | 0.9 (2) |
C3—C1A—C2A—C3A | −178.56 (16) | C2—O1—C9—C8 | −176.83 (15) |
O2A—C2A—C3A—C4A | 179.01 (16) | C7—C8—C9—O1 | 176.92 (15) |
C1A—C2A—C3A—C4A | −1.0 (3) | C4B—C8—C9—O1 | 1.0 (2) |
C2A—C3A—C4A—O4A | −179.39 (16) | C7—C8—C9—C10 | −0.9 (2) |
C2A—C3A—C4A—C5A | 0.8 (3) | C4B—C8—C9—C10 | −176.78 (17) |
O4A—C4A—C5A—C6A | −179.83 (17) | C6—C5—C10—C9 | −0.3 (3) |
C3A—C4A—C5A—C6A | 0.0 (3) | C6—C5—C10—C4 | −175.28 (17) |
C4A—C5A—C6A—C1A | −0.6 (3) | O1—C9—C10—C5 | −176.79 (16) |
C2A—C1A—C6A—C5A | 0.3 (3) | C8—C9—C10—C5 | 0.8 (2) |
C3—C1A—C6A—C5A | 179.32 (16) | O1—C9—C10—C4 | −1.7 (3) |
C9—O1—C2—C3 | 31.4 (2) | C8—C9—C10—C4 | 175.90 (16) |
C6A—C1A—C3—C2 | 100.6 (2) | C3—C4—C10—C5 | 146.12 (17) |
C2A—C1A—C3—C2 | −80.5 (2) | C3—C4—C10—C9 | −28.8 (2) |
C6A—C1A—C3—C4 | −21.8 (2) | C6—C7—O1B—C2B | 154.92 (16) |
C2A—C1A—C3—C4 | 157.13 (16) | C8—C7—O1B—C2B | −30.2 (2) |
O1—C2—C3—C1A | 172.12 (15) | C7—O1B—C2B—C3B | 42.0 (2) |
O1—C2—C3—C4 | −61.09 (19) | C7—O1B—C2B—C5B | 161.71 (15) |
C1A—C3—C4—C10 | −177.75 (14) | C7—O1B—C2B—C6B | −79.32 (19) |
C2—C3—C4—C10 | 57.45 (18) | O1B—C2B—C3B—C4B | −29.3 (2) |
C10—C5—C6—C7 | −0.2 (3) | C5B—C2B—C3B—C4B | −144.71 (18) |
C5—C6—C7—O1B | 174.93 (16) | C6B—C2B—C3B—C4B | 90.1 (2) |
C5—C6—C7—C8 | 0.1 (3) | C2B—C3B—C4B—C8 | 3.9 (3) |
C6—C7—C8—C9 | 0.4 (3) | C7—C8—C4B—C3B | 11.4 (3) |
O1B—C7—C8—C9 | −174.32 (15) | C9—C8—C4B—C3B | −172.65 (17) |
Hydrogen-bond geometry (Å, º) topCgA is the centroid of the C1A–C6A ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4A—H4A···O1Bi | 0.86 (3) | 1.96 (3) | 2.8214 (19) | 178 (2) |
O2A—H2A···CgAii | 0.84 (3) | 2.46 (2) | 3.1505 (16) | 139 (2) |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) x+1/2, −y+3/2, −z. |
One-dimensional 1H NMR data [δH, (m, J in Hz)]
of glabridin in DMSO d6 and CDCl3 (600 MHz) topProtons | DMSO d6 | CDCl3 |
H-2 (pro-S) a | 3.94 (t, JH-3 = 10.26) | 4.01 (t, JH-3 = 10.56) |
H-2 (pro-R) b | 4.23 (dt, JH-4a = 2.61, Jgem = -10.20) | 4.37 (dt, JH-4a = 2.55, Jgem = -10.56) |
H-3 | 3.29 (m) | 3.48 (m) |
H-4 (pro-S) a | 2.69 (ddd, JH-2b = 1.76, JH-3 = 4.77, JH-4b = 15.52) | 2.86 (ddd, JH-2b = 1.57, JH-3 = 4.71, JH-4b = 15.62) |
H-4 (pro-R) b | 2.89 (dd, JH-3 = 11.36, JH-4a = 15.52) | 2.97 (dd, JH-3 = 10.77, JH-4a = 15.62) |
H-5 | 6.83 (d, JH-6 = 8.22) | 6.82 (d, JH-6 = 8.23) |
H-6 | 6.29 (d, JH-5 = 8.22) | 6.36 (d, JH-5 = 8.23) |
H-3A | 6.33 (d, JH-5A = 2.40) | 6.33 (d, JH-5A = 2.30) |
H-5A | 6.19 (dd, JH-3A = 2.40, JH-6A = 8.32) | 6.38 (dd, JH-3A = 2.30, JH-6A = 8.37) |
H-6A | 6.86 (d, JH-5A = 8.32) | 6.95 (d, JH-5A = 8.37) |
2A-OH | 9.11 (s) | |
4A-OH | 9.39 (s) | |
H-3B | 5.65 (d, JH-4B = 9.90) | 5.55 (d, JH-4B = 9.90) |
H-4B | 6.54 (d, JH-3B = 9.90) | 6.64 (d, JH-3B = 9.90) |
H3-5B | 1.33 (s) | 1.40 (s) |
H3-6B | 1.34 (s) | 1.42 (s) |
Chemical shifts δ in p.p.m.. Coupling patterns are given in parentheses
(J in Hz). All assignments were confirmed by gHSQC and qHMBC. |
Results of one-dimensional 1H NMR full-spin analysis of glabridin in DMSO
d6 (δH, m, J in Hz) topProtons | DMSO d6 |
H-2 (pro-S) a | 4.271 (t, JH-3 = 10.29, Jgem = -10.25) |
H-2 (pro-R) b | 4.319 (dt, JH-3 = 3.49 Jgem = -10.25, JH-4a = 2.11) |
H-3 | 3.359(dddd, JH-2a = 10.29, JH-2b = 3.49, JH-4a = 4.85,
JH-4b = 11.36) |
H-4 (pro-S) a | 2.703 (ddd, JH-2b = 2.11, JH-3 = 4.85, JH-4b = 15.59) |
H-4 (pro-R) b | 2.776 (dd, JH-3 = 11.36, JH-4a = 15.59, JH-5 = -0.90) |
H-5 | 7.140 (d, JH-6 = 8.22) |
H-6 | 6.487 (d, JH-5 = 8.22) |
H-3A | 6.356 (dd, JH-5A = 2.40, JH-6A = 0.44) |
H-5A | 6.330 (dd, JH-3A = 2.40, JH-6A = 8.32) |
H-6A | 7.036 (dd, JH-3A = 0.44, JH-5A = 8.32) |
2A-OH | 9.418 (s) |
4A-OH | 9.919 (s) |
H-3B | 6.337 (d, JH-4B = 9.91) |
H-4B | 7.111 (d, JH-3B = 9.91) |
H3-5B | 1.392 (s) |
H3-6B | 1.405 (s) |
Comparison of bond lengths (Å) for glabridin in this work and
with those from Tantishaiyakul et al. (2012) topAtom 1 | Atom 2 | This work | Tantishaiyakul et al. |
C1A | C6A | 1.396 (3) | 1.388 (3) |
C1A | C2A | 1.408 (2) | 1.398 (3) |
C1A | C3 | 1.516 (2) | 1.506 (3) |
C2A | O2A | 1.376 (2) | 1.369 (3) |
C2A | C3A | 1.393 (2) | 1.383 (3) |
C3A | C4A | 1.396 (3) | 1.380 (3) |
C4A | O4A | 1.369 (2) | 1.361 (3) |
C4A | C5A | 1.389 (3) | 1.377 (3) |
C5A | C6A | 1.396 (3) | 1.384 (3) |
O1 | C9 | 1.375 (2) | 1.372 (3) |
O1 | C2 | 1.455 (2) | 1.442 (2) |
C2 | C3 | 1.525 (3) | 1.516 (3) |
C3 | C4 | 1.536 (3) | 1.528 (3) |
C4 | C10 | 1.508 (2) | 1.501 (3) |
C5 | C10 | 1.394 (3) | 1.385 (3) |
C5 | C6 | 1.392 (3) | 1.386 (3) |
C6 | C7 | 1.384 (3) | 1.370 (3) |
C7 | O1B | 1.389 (2) | 1.380 (3) |
C7 | C8 | 1.401 (3) | 1.389 (3) |
C8 | C9 | 1.406 (2) | 1.400 (3) |
C8 | C4B | 1.459 (3) | 1.449 (3) |
C9 | C10 | 1.400 (3) | 1.386 (3) |
O1B | C2B | 1.471 (2) | 1.463 (3) |
C2B | C3B | 1.512 (3) | 1.493 (4) |
C2B | C5B | 1.521 (3) | 1.516 (3) |
C2B | C6B | 1.526 (3) | 1.524 (4) |
C3B | C4B | 1.337 (3) | 1.321 (3) |
O2A | H2A | 0.84 (3) | 0.802 (17) |
C3A | H3A | 0.97 (2) | 0.93 |
O4A | H4A | 0.86 (3) | 0.820 (17) |
C5A | H5A | 0.97 (2) | 0.93 |
C6A | H6A | 0.96 (2) | 0.93 |
C2 | H21 | 0.99 (2) | 0.97 |
C2 | H22 | 1.00 (2) | 0.97 |
C3 | H3 | 0.97 (2) | 0.98 |
C4 | H41 | 0.99 (2) | 0.97 |
C4 | H42 | 0.98 (2) | 0.97 |
C5 | H5 | 0.97 (2) | 0.93 |
C6 | H6 | 0.98 (2) | 0.93 |
C3B | H3B | 1.00 (2) | 0.93 |
C4B | H4B | 0.96 (2) | 0.93 |
C5B | H5B1 | 1.01 (3) | 0.96 |
C5B | H5B2 | 0.98 (3) | 0.96 |
C5B | H5B3 | 0.99 (3) | 0.96 |
C6B | H6B1 | 0.96 (3) | 0.96 |
C6B | H6B2 | 0.99 (3) | 0.96 |
C6B | H6B3 | 1.04 (3) | 0.96 |
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