Absolute configuration of naturally occurring glabridin

Simmler, C.; Fronczek, F.R.; Pauli, G.F.; Santarsiero, B.D.

doi:10.1107/S0108270113018842

Absolute configuration of naturally occurring glabridin

C. Simmler, F. R. Fronczek, G. F. Pauli and B. D. Santarsiero

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.

Keywords: crystal structure; absolute configuration; glabridin; natural compounds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113018842/ln3162sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270113018842/ln3162Isup2.hkl Contains datablock I
	Chemdraw file https://doi.org/10.1107/S0108270113018842/ln3162Isup3.cdx Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113018842/ln3162Isup4.cml Supplementary material

Computing details top

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-[(3R)-8,8-Dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol top

Crystal data top

C₂₀H₂₀O₄	D_x = 1.343 Mg m⁻³
M_r = 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	R_int = 0.046
φ and ω scans	θ_max = 68.5°, θ_min = 4.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→7
T_min = 0.895, T_max = 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(F_o²) + (0.0324P)² + 0.3419P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2879 reflections	Δρ_max = 0.13 e Å⁻³
277 parameters	Δρ_min = −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	U_iso*/U_eq
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) top

CgA 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 [δ_H, (m, J in Hz)] of glabridin in DMSO d₆ and CDCl₃ (600 MHz) top

Protons	DMSO d₆	CDCl₃
H-2 (pro-S) a	3.94 (t, J_H-3 = 10.26)	4.01 (t, J_H-3 = 10.56)
H-2 (pro-R) b	4.23 (dt, J_H-4a = 2.61, J_gem = -10.20)	4.37 (dt, J_H-4a = 2.55, J_gem = -10.56)
H-3	3.29 (m)	3.48 (m)
H-4 (pro-S) a	2.69 (ddd, J_H-2b = 1.76, J_H-3 = 4.77, J_H-4b = 15.52)	2.86 (ddd, J_H-2b = 1.57, J_H-3 = 4.71, J_H-4b = 15.62)
H-4 (pro-R) b	2.89 (dd, J_H-3 = 11.36, J_H-4a = 15.52)	2.97 (dd, J_H-3 = 10.77, J_H-4a = 15.62)
H-5	6.83 (d, J_H-6 = 8.22)	6.82 (d, J_H-6 = 8.23)
H-6	6.29 (d, J_H-5 = 8.22)	6.36 (d, J_H-5 = 8.23)
H-3A	6.33 (d, J_H-5A = 2.40)	6.33 (d, J_H-5A = 2.30)
H-5A	6.19 (dd, J_H-3A = 2.40, J_H-6A = 8.32)	6.38 (dd, J_H-3A = 2.30, J_H-6A = 8.37)
H-6A	6.86 (d, J_H-5A = 8.32)	6.95 (d, J_H-5A = 8.37)
2A-OH	9.11 (s)
4A-OH	9.39 (s)
H-3B	5.65 (d, J_H-4B = 9.90)	5.55 (d, J_H-4B = 9.90)
H-4B	6.54 (d, J_H-3B = 9.90)	6.64 (d, J_H-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 (δ_H, m, J in Hz) top

Protons	DMSO d₆
H-2 (pro-S) a	4.271 (t, J_H-3 = 10.29, J_gem = -10.25)
H-2 (pro-R) b	4.319 (dt, J_H-3 = 3.49 J_gem = -10.25, J_H-4a = 2.11)
H-3	3.359(dddd, J_H-2a = 10.29, J_H-2b = 3.49, J_H-4a = 4.85, J_H-4b = 11.36)
H-4 (pro-S) a	2.703 (ddd, J_H-2b = 2.11, J_H-3 = 4.85, J_H-4b = 15.59)
H-4 (pro-R) b	2.776 (dd, J_H-3 = 11.36, J_H-4a = 15.59, J_H-5 = -0.90)
H-5	7.140 (d, J_H-6 = 8.22)
H-6	6.487 (d, J_H-5 = 8.22)
H-3A	6.356 (dd, J_H-5A = 2.40, J_H-6A = 0.44)
H-5A	6.330 (dd, J_H-3A = 2.40, J_H-6A = 8.32)
H-6A	7.036 (dd, J_H-3A = 0.44, J_H-5A = 8.32)
2A-OH	9.418 (s)
4A-OH	9.919 (s)
H-3B	6.337 (d, J_H-4B = 9.91)
H-4B	7.111 (d, J_H-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) top

Atom 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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