X-Ray Diffraction Powder Data for the Steroids WILLIAM T. BEHER, JONATHAN PARSONS, and GIZELLA D. BAKER The Edsel
B. Ford Institute for M e d i c a l Research,
Henry Ford Hospital, Detroit 2, M i c h . ~
X-ray diffraction powder data and powder diffraction photographs for 39 steroids are presented.
Table I. 52
(deoxycorticosterone acetate) Allopregnane-2 1-01-3,20-dione-2 l-acet a t e ( 2 1-acetoxyallopregnanedione) A'-Pregnene-3,20-dione-21-01 (deoxycorticosterone) A'-Pregnene-3,20-dione-17-01 (17-hydroxyprogesterone)
53
S
ISCE the publication of the previous paper (3) on x-ray diffraction data for steroids, a number of additional com-
54 J5
pounds have become available for study. The data and diffraction patterns obtained are here presented. The procedure followed was identical with that outlined in the previous paper (3) with the exception of the method of deteimining relative intensities. The relative intensities, which are presented with these 39 patterns, were measured using a technique of graded intensity scale comparison, developed by HannWalt, Rinn, and Frevel ( 1 ) and modified by Klug and Alexander
K. Kl
K3
L. Dihydroxytriketones A'-Preenene-3.11.20-trione-l7iu)21A'-Pregnene-3,11,20-trione-I7(u) $1diol ?cortisone) (cortisone) A'-Pregnene-I7(a) ,21-diol-3,11,20-tn,21-diol-3,11,20-trione-21-acetate (cortisone acetate)
L1
L2
Table I. Pattern No.
Index to X-Ray Diffraction Powder Data on Steroids
Name C~Q-Z STEROIDS Q 4 . llonochloro 3(B)-Chloro-A~-cholestene (cholesteryl chloride) B. Monohydric Alcohols 3(p)-Cholestane-3-acetate (dihydrocholesterol acetate) 22,23-Dihydrostigmas terol-3-acetate (B-sitos terol acetate) Stigmasta-Ab,*2-dien-3(p)-ol-3-acetate (stigmasterol acetate) As-Cholestene-3-01-3-acetate (cholesterol acetate)
M.P. JUncor.), C.
B1 B2 B3 B4
92
-217
207
-210
236
-237.5
195.5-197.5
222
-225
236
-240
S1 s 2 53 x5
111. STEROIDSAPOGLXINS A N D DERIVATIVES Sarsasapogenin 198 -201 Diosgenin acetate 195 -197 Cholesterol digitonide ... 8-Sitosterol digitonide . . 45-Androstene benzoate digitonide
01 02 03
Gitoxin Digoxin Digitoxin
>-4
108 -109
215
11. BILE ACIDS Hyodeoxycholic acid Lithocholic acid (3u-hydroxycholanic acid)
A12
-94
-196
138 -141
RI 1
I.
.I 1
155 -157 104
Dihydroxydiketones
A'-Pregnene-l*i(a) .21-diol-3,20-dione [Reichstein's Substance S (alcohol) ] Ad-Pregnene-l7(~),21-dio1-3,20-dione-21acetate [Reichstein's Substance 9 (acetate) ] Pregnane-l7(u) ,2 l-diol-3,20-dione-Z1acetate
K2
(2).
(Continued)
A'-Pregnene-3,2O-dione-21-01-2l-acetate
185 -187
IT. DIGITALIS GLYCOSIDES
125 -127 140 -141.5
Dec. 282 260 -265 245 -249
115 -116
C.
C1 c2 C3
Dihydric .4lcohols Pregnane-a(u) ,ZO(u)-diol Pregnane-3(a) 2 0 (@)-diol 17(a)-Methyl- As-andros tene-3 (0).17 ( B ) diol (mestenediol) D.
D1
Table 11. X-Ray Diffraction Powder Data
237 -230 232,5-235 204
d, 4 .
Monoketones
Cholestane-3-one (cholestanone)
F1 F2
Diketones Pregnane-3,20-dione (pregnanedione) F . Monohydroxymonoketones Allopregnane-3(p)-o1-20-one (allopregnanolone) Ab- Andros tene-3 (0) -01- 17-one-3 methyl ether (dehydroepiandrosterone methyl -the?\
15.4 10.5 7.90 6.89 6.13 5,49 4.66
117 -120
H1
H. Trihydroxymonoketones A4-Pregnene- 17a,?Oh,2I-triol-3-one!Oh,21-diacetate (17a-pregnentriolone diacetate)
188 -190.3
I1
I. Tetrahydroxymonoketones 3(u),17(u),11 (p),ZI-Tetrol-pregnane-ZOone (tetrahydrocortisone)
216
G1
G2 G3
J1
117.5-120 173 -175
163
-165
185 -189 -2i6
-2I8
5. Monohydroxydiketones 16,17-0xido-A~-pregnene-3,20-dione-21ol-21-acetate (16.17-epoxydeoxycorticosterone acetate)
166 -168
1569
3(8)-Cholestane3-acetate 16.7 0.20 10.0 O,l5 9.02 0.07 7.47 0.15 0.07 6.81 1.00 6.09 5.72 0 50 5.31 0.27 4.89 0.27 4.68 0.37 4.47 0.27 4.18 0.37 3.81 0.20 3.55 0.20 3.28 0.15 3.07 0.20 2.89 0.20 2.79 0.10 2.68 0.15 2.51 0.15 2.41 0.10 2.26 0 20 2.20 0.15 2.04 0 15 1.90 0.15 1.83 0.03 0.01 1.77 1.72 0.01 1 ..SI 0.01
llonohydric Alcohols B2. 22.23-Dihydrostigmasterol-3-acetate 12.8 0.13 6.40 0.07 6.07 1.00 5,74 0.20 5.42 0.02 5.10 0.53 4.86 0.40 4.16 0.02 3.75 0.20 3.51 0.02 3.10 0.20 3.02 0.13 2.94 0.07 2.60 0.02 2.43 0.03 2.14 0.07 2.02 0.07 1.94 0.02 B3. Stigmasta-Ajr22dien-3(s)-ol-3-acetate 16.5 0.04 10 2 0.04 9.21 0.20 7.60 0.04 7.03 0.49 8.19 0.36 5 75 0.13 5:44 0.13
d , A.
I/Ii
2.78 2.58 2.49 2.27 2.16 2.05 1.93
0.03 0.02 0.07 0.13 0.07 0.13 0.02
B. B1.
137.5-140.5
272
F4
0.13 0.53 0.13 0.20 0.40 1.00 0.53
192 -1q5
I/Ii C~Q-A STEROIDS Q
.1. blonochloro 3(f3)-Chloro-As-cholestene 4.32 0.20 3.95 0.30 3.78 0.07 3.54 0.30 3.21 0.03 $07 0.03 -.94 0.03
Al.
128 -129
~4I.~nd;ostene-17(8)-01-3-one~17-propionate (testosterone propionate) AS t '6-Pregnadiene-3 (B)-ol-20-one-3-acet a t e (16-dehydropregnenolone acetate) G. Dihydroxymonoketones Ab-Pregnene-3 (p), 2 l-diol-20-one-3.21diacetate (21-acetoxypregnenolone acetate) 16.17-0xido-A5-pregnene-3(p) ,21-diol20-one-2 1-acetate (16,17-epoxy-21acetoxypregnenolone) As-Pregnene-3(@), 17-diol-20-one (17hydroxypregnenolone)
F3
d , A.
I.
E.
El
I/I,
-205
B 3. Contd. 5.10 0.13 1.00 4.87 4.66 0.20 4.30 0.13 4.12 0.13 3.98 0.13 3.87 0.13 0.13 3.78 3.74 0.27 3.59 0.13 0.13 3.38 3.26 0.13 3.10 0.13 3.02 0.01 2.94 0.01 2.78 0.01 0.13 2.57 0.13 2.50 0.13 2.39 2.34 0.13 2.28 0.20 2.21 0.13 2.14 0.01 2.09 0.20 2.00 0.01 1.94 0.01 0.02 1.88 1.82 0.02 1.78 (Continued on p a g e 1 6 7 1 )
ANALYTICAL CHEMISTRY
1570
.
...
...._* -
,
Figure 1. X-ray diffraction powder patterns of steroids Key found in Tabla
V O L U M E 2 7 , NO. 10, O C T O B E R 1 9 5 5
1571
Table 11. X-Ray Diffraction Powder Data (Continued) d , A.
I/Ii B4.
d , A. 1/11 d , A. A5-Chokatene-3-01-3-acetate 4.13 3.70 3.53 3.12 2.97 2.88 2.75 2.65 2 47 2.39
16.36 13.81 10.40 8.23 7.06 6.17 5.42 4.77 4.58 4.33
C. Pregnane-S(a), 20(a)-diol 0.38 12.3 0.38 9.46 0.38 7.83 7.03 0.75 6.33 0.25 5.79 1.00 0.25 5.35 1.00 5.08 0.75 4.68 4.42 0.03 4.12 0.56 0.03 3.93 0.38 3.79 3.46 0.38 3.17 0.06 0.03 3.08 0.03 2 95 0.25 2.55 2.48 0.25 2.41 0.25 2.30 0.03 2.15 0.38 0.03 2.06 2.01 0.03 0.13 1.97
c1.
0.27 0.37 0.27 0.20 0.15 0.10 0.10 0.10 0.20 0.20
C2.
Pregnane-a(a),20(8)-diol
11.6 10.5 9.07 8.39 7.17 6.44 5.83 5.32 4.87 4.49 4.14 3.92 3.69 3.68 2.71 2.52 2.35 2.21
0.55 0.05 0.27 0.55 0.55 0.55 0.73 1.00 0.41 0.41 0.41 0.41 0.41 0.05 0.02 0.02 0.02 0.02
d , A.
1/11
C3. 17(a ) - M e t hyl- Asandrostene-3(8),17(8)diol 12.1 0.13 10.5 0.13 9.46 0.03 8.47 0.07 7.09 0.30 6.37 0.53 5.75 1.00 5.38 0.53 4.85 0.40 4.53 0.30 4.32 0.40 4,l5 0.30 3.78 0 20 3.56 0.30 3.29 0.30 3.11 0.03 2.99 0.03 2.84 0.40 2.70 0.02 2.53 0.02 2.43 0.03 2.16 0.02 2.08 0.03
1/11
D.
hlonoketonm Cholestane-3-one 0.13 0.13 0.01 0.27 0.09 0.13 0.13 0.13 1.00 0.67 0.27 0.20 0.20 0.13 0.13 0.20 0.20 0.01 0.01 0.01 0.13 0.04 0.04 0.04 0.02 0.01 0.01
16.7 12.7 11.3 9.66 8.59 7.87 7.34 6.45 5.54 4.95 4.56 4.21 3.92 3.68 3.51 3.37 3.23 3.08 3.00 2.90 2.54 2.45 2.38 2.30 2.22 2.09 1.99
E. El.
F2. As-Androstene3tp)-ol-li-one-3 methyl ether 0.11 11 2 0.20 9 35 7 83 0.010.53 6.76 1.00 6.26 0.11 5 74 0.20 5.20 0.20 4 66 0.53 4.42 0.11 4.23 0.11 4 08 3.88 0.08 0.08 3.70 0.11 3 58 0.15 3.39 0.11 3.28 0.15 3.09 0.11 2 92 0.012 78 0.08 2.69 2.55 0.08 2.41 0.11 0.012.32 2.22 0.15 0.01 2.10 0.01 2.07 2.01 0.08 1 91 0.15 1.81 0.01 1.79 0.01 1.76 0.011.70 0.011.65 0.011.63 0.01 0.011.57 0.011.50
Allopregnane3(p)-ol-ZO-one
8.59 6.66 6.33 5.70 5 49 5.15 4.89 4.65 4.44 4.21 4.10 3.80 3.68 3.49 3.29 3.19 2.99 2.77 2.44 2.38 2.25 2.18
0.30 0.30 0.40 1.00 0.30 0.02 0.53 0.02 0.02 0.53 0.30 0.02 0.02 0.40 0.13 0.03 0.03 0 03 0.30 0.30 0.07 0.30
F4.
D1.
d . A. I/Il d , A. f. Monohydroxymonoketones
F1.
Dihydric .4lcohols
d , A.
10.3 6.56 6.28 5.79 5.56 5.11 4.46 3.91 3.53 3.40 3.13 2.97 2.88 2.77 2.67 2.53 2.43 2.39 2.23 2.16 2.10 2.01 1.96
I'Ii
Diketones
Pregnane-3,ZO-dione 0.20 0.20 1.00 0.73 0.73 0.53 0.53 0 20 0.40 0.13 0.07 0.13 0.07 0.07 0.07 0.03 0.07 0.03 0.07 0.13 0.03 0.03 0.13
Ij11
F3. A'-Androstene17(p)-01-3-one- 17propionate 10.8 0.36 7.54 0.27 7.14 0.36' 6.09 1.00 0.67 5.49 0.13 5.08 0.04 4.84 0.67 4 71 0.27 4.40 4.22 0.04 0.27 3.97 0.27 3.87 0.01 3.73 0.27 3.60 0.27 3.45 0.09 3.24 0.09 3.11 0.27 2.95 2.87 0.13 0.13 2.80 0.09 2.73 0.09 2.68 2.60 0.09 2.55 0.09 2.50 0.02 2.45 0.04 0.04 2.41 0.04 2.37 2.28 0.27 0.02 2.22 0.27 2,15 2.01 0.04 2.01 0.02 0.02 1.98 0.02 1.94
A5,16-Pregnadiene-3(p)-o1-20-one-3-acetate
19.0 11.6 9.36 6.89 6.33 6.17 5.77 5.50 5.35 5.05 4.67 4.52 4.33 4.13 3.94 3.85 3.69
3.58 3.49 3.41 3.34 3.16 3.07 3.01 2.88 2.77 2.73 2.66 2 59 2.50 2.43 2.36 2.31 2.28 G.
2.23 2.17 2.13 2.07 2.01 1.96 1.93 1.89 1.85 1.77 1.74 1.71 1.66 1.62
0.18 0.18 0.02 0.09 0.09 0.02 0.18 0.09 0.09 0.09 0.02 0.02 0.02 0.02
Dihydroxymonoketones
G1. AS-Pregnene-3(8), 21-diol-20-one 3,21G2 (Contd.) diacetate 5 67 0.30 15.5 0.13 7.83 0.07 5.37 0.53 6.61 0.02 5.04 0.53 6.09 0.73 4 65 * 0.40 5.64 0.53 4 29 0.53 4 10 0.53 5.33 0.30 5.19 0.30 3.92 0.40 5.00 0.13 3 56 0.02 4.75 1.00 3.37 0.53 4.45 0.13 3.27 0.02 4.28 0.07 3.19 0.02 3.90 0.40 3.08 0.30 3.76 0.40 2.92 0.02 3.56 0.40 2 83 0.07 3.40 0.07 2.75 0.13 2.70 0.13 3.03 0.30 2.85 0.30 2.58 0.02 2.74 0.13 2.54 0.02 2.60 0.07 2 39 0.07 2.51 0.07 2 33 0.07 2.41 0.02 2.18 0.13 2.36 0.07 2 04 0.07 2.28 0.07 1 96 0.02 2.21 0.07 1.82 0.02 2.15 0.02 2.08 0.07 G3. A5-Pregnene-3(@), 2.11 0.07 17-diol-20-one 2.01 0.02 12 1 0.27 1.93 0.02 8.01 1.00 1.84 0.02 5 83 1.00 5 06 0 .75 G2. 16,17-0xido-A64.88 0.21 pregnene-3 (8),21-diol4 . 6 2 0 . 27 20-one-2 1-acetate 4.30 0.75 9.35 0.73 4.08 0.20 6.15 1.00 3.75 0.10
G3. ( C o n t d . ) 3.62 0.20 3.52 0.10 3.40 0.15 3.31 0.15 3.17 0 1.5 3.08 0.15 3.00 0.2i 2.92 0 15 2.86 0.15 2.82 0 15 2.74 0 10 2.68 0 15 2.57 0.03 2.47 0.03 2.42 0.02 2 38 0 07 2.36 0.03 2.30 0.07 2.28 0.07 2.21 0.03 2.13 0.01 2.08 0.20 2 04 0.20 2.01 0.01 1.99 0.20 1.95 0 20 1.92 0.01 1.90 0.01 1.88 0 01 l,85 0.07 1.83 0.03 1.74 0.03 1.68 0.03 1.64 0.02 1.57 0.01 1.54 0.01 1.52 0.03 1.47 0.01 1.45 0.01
ANALYTICAL CHEMISTRY
1572
Table 11. X-Ray Diffraction Powder Data (Continued) d , A.
HI.
d , A. I/Il H. Trihydroxymonoketones A~-Pregnene-17a,20b,2l-triol-3-one-2Ob,2l-diacetate
I/Il
11.19 8.55 7.14 6.28 5.79 5.50 4.65 4.28 4.08 3.87 3.72 3.58 3.45 3.32 3.24
11.
3.14 3.06 2.92 2.81 2.70 2.60 2.40 2.21 2.15 2.08 2.01 1.92 1.83 1.76
54.
0.15 0.15 0.09 0.10 0.10 0.09 0.15 0.09 0.09 0.10 0.04 0.04 0.02 0.01
I. Tetrahydroxymonoketones 3 ( a ) ,17(a),11@),2l-Tetrol-pregnane-20-one 2.89 2.82 2.76 2.67 2.55 2.50 2.44 2.30 2.24 2.23 2.16 2.11 2.06 1.98 1.93 1.89 1.85 1.81
1/11 d , A. 1/11 J. Monyhydroxydiketone (Contd.) 44-Pregnene-3,20-dione-21-01 55. 34-Pregnene-3,20-dione-17-01 11.7 0.06 11.4 0.08 6.54 0.08 5.91 1.00 5.45 0.20 4.90 0.30 4.54 0.20 0.06 4.19 0.20 4.10 0.06 3.92 0.20 3.63 0.04 3.48 0.04 3.36 0.06 3.26 0.11 3.12 0.013.04 2.84 0.06 0.11 2.66 2.52 0.11 2.46 0.04 2.34 0.11 0.11 2.31 0.03 2.22 0.08 2.10 2.01 0.03 0.08 1.96 0.01 1.91 0.08 1.86 0.01 1.81 0.01 1.75 1.64 0.06 0.06 1.54 0.03 1.39 1.25 0.01d,
0.13 0.02 0.13 0.13 0.07 0.03 0.40 0.40 0.13 0.02 0.13 0.13 0.07 0.13 0.02 0.02 0.02 0.07
d , .I.
.I.
I/ll
K. ICl. d , A.
d , -4.
1/11 J.
J1. 16,17-0xido-A(pregnene-3,20-dione-2101-21-acetate 0.13 0.13 0.20 0.03 0.03 1.00 0.73 0.53 0.53 0.03 0.53 0.07 0.03 0.02 0.03 0.13 0.20 0.07 0.07 0.07 0.02 0.02 0.40 0.13 0.07 0.03 0.03 0.13 0.13 0.13 0.02 0.13 0.02
I/Ii
d , A.
I/Ii
Monohydroxydiketones 52. 4a-Pregnene-3,20dione-21-01-21-acetate 11.4 0.13 8.23 0.13 7.23 0.27 6.23 0.27 0.04 5.89 0.m 5.59 1.00 5.33 0.27 5.11 0.27 4.90 4.62 0.27 4.50 0.02 4.37 0.27 4.20 0.36 3.98 0.02 3.81 0.09 3.60 0.36 3.38 0.01 3.24 0.20 3.15 0.20 3.00 0.20 0.20 2.93 2.81 0.20 2.74 0.20 2.65 0.01 2.57 0.20 2.48 0.20 2.43 0.20 2.35 0.20 2.30 0.01 0.20 2.26 2.21 0.20 2.16 0.02 0.13 2.01 1.98 0.01 0.01 1.84
53. Allopregnane-2 1ol-3,20-dione-21acetate 7.00 6.68 6,56 6.33 6.19 5.79 5.22 5.10 4.94 4.68 4.59 4.39 4.13 3.87 3.75 3.63 3.54 3.43 3.33 3.24 3.09 3.04 2.98 2.94 2.82 2.72 2.65 2.61 2.56 2.52 2.48 2.38 2.25 2.20 2.18 2.15 2.12 2.08 * 2.04 2.00 1.96 1.87 1.77 1.66
A'-Pregnene-l7(a). 2 l-diol-3,20-dione 10.9 0.05 8.35 0.09 6.33 0.73 5.59 1.00 5.29 0.73 4.58 0.02 4.33 0.02 4.17 0.73 0.05 3.66 0.02 3.71 0.27 3.69 0.18 3.40 0.18 3.29 0.41 3.18 0.27 3.08 0.09 2.96 0.09 2.81 2.67 0.18 2.59 0.27 2.40 0.27 0.02 2.23 0.18 2.18 0.09 2.09 0.18 2.04 0.02 2.00 0.02 1.96 0.02 1.89 0.09 1.84 0.02 1.79 0.09 1.69
d , A. 1/11 d , b. I/Ii Dihydroxydiketones K2. A4-PregneneK3. Pregnane-lT(a) .2117(a),21-diol-3,20diol-3,20-dione-21dione-21-acetate acetate 11.1 13.1 8.31 6.89 7.23 6,56 6.24 6.24 5.91 5.85 5.59 5.70 5.50 5.32 5.22 5.10 4.87 4.93 4.68 4.80 4.42 4.52 4.39 4.25 4.21 4.18 3.82 4.09 3.96 3.60 3.24 3.85 3.13 3.75 3 04 3.64 2.94 3.47 2.84 3.33 2.75 3.28 2.71 3.18 2.66 3.12 2.62 3 06 2.98 2.55 2.92 2.47 2.83 2.34 2 30 2 74 2.24 2 67 2.19 2 62 2 , 26 2.58 2.11 2.53 2.06 2.47 2.01 2.44 2.40 1.98 2.36 1.93 2.31 1,87 2.27 1.82 2.21 1 77 2 15 1.73 2.09 2.05 1.98 1.95 1.91 1.87 1.83 1.80 1.74 1.68 1.59 1.53
V O L U M E 27, NO. 10, O C T O B E R 1 9 5 5
1573 ________~~
~__
Table 11. X-Ray Diffraction Powder Data (Continued) d , A.
III; L.
d , A:
111.
I[. Hyodeoxycholic w i d 14.6 0.20 0.13 1O.Y 9.21 0.53 0.40 7.63 0.13 6.26 1.00 6.83 0.40 5.59 0.40 5,29 4.91 0.53 4.51 0.33 0.30 4.27 4.11 0 40 0.07 3.95 0.40 3.73 0.07 3.60 0.40 3.41 0.30 3 25 0.30 3.13 0 . 20 3.04 0.07 2.86 0.07 2.76 0.13 2.70 0.13 2.01 2 . .55 0 0: 2.47 0.30 2.40 0.30 0.30 2.34 0 30 2.22 2.15 0.13 2.10 0.18 2.00 0.30 0.13 1.99 0.13 1.88
13.1 9 07 7.23 0.13 6 . 15 5.81 5 01 5.39 5.05 4 76 4.48 4 32 4.20 4.03 3.88 3.74 3.57 3 46 3.3li 3.23 3 . 10 2.90 2.80 2 0.; 2 56 2 48 2 3.5 2.26 2 23 2 lli 2 OR 2 03 1.98 1 90 1.87 1.82 1.74 1.66
d , A. IIII d , A. I/Ii 111. STEROIDSAPOGEKIXS A X D DERIV.%TIYEB (Contd.) N l . (Contd.) N2. (Contd.)
I/I:
Dihydrovytriketonez L I . 34-Pregnene-3.1 1,20-trione17(o1),21-diol L2. (Contd.) 4 , ti> 0 10 4.29 0 li 4.15 0 03 4.00 0 10 0 0: 3.83 0 211 3.73 0 0-7 3.58 0 15 3 43 0 15 3.32 0 10 3.11 0 IO 3.06 0 10 2.97 2 89 o zn 0 02 2 74 2.07 0 07 2.64 0 01 2.58 0 0! 0 0: 2 52 0 07 2.43 0 07 2 38 0 0: 2 30 0 li 2.21 0 01 2.17 0 03 2 12 0 02 2.07 0 02 2.05 0 10 1.99 I.?. ~'-Preenene-l'i(cr),Zi-diol0 03 1.94 3 11.20-trione-21-acetate 0 03 1 91 7 34 0 1.7 1.86 0 0' 6 19 o 50 0 07 1.82 5 93 0 37 0 03 1.74 5 49 0 Ii 0 03 1.73 0 07 5 10 0 03 1 68 1 6 4 0 03 4 94 1 00
0.20 0.02 0 20 0 20 0.33 1.00 0.73 0.01'
0.53 0.4?
0.73 0 53 0.4'7 0.40
0.0.' 0.44) 0.3') 0 4!? 0.30 0 30 0.02 0.02 0 07 0 . 2'1 0.19
0.2f) 0.20 0.31) 0.20 0.0'' 0 311 0.02 0 . 20 0.02 0.07 0 02 0 02 0 02
111. STEROIDSAPOGEXIXS AXD DERIVATIVES Sarsasapogenin N2. Diosgenin acetate 13.5 0.13 14.0 0 13 12 0 0 20 9.41 0.13 9.82 0.39 7.03 0.l3 8.59 0.40 6.11 0 ,s 7.63 0.30 5.72 1.0'1 6.94 0 40 5.44 0.03 5.54 1 00 r, 21 0 .40 4.98 0.53 4.72 0 40 4 62 0.40 4.38 0.40 4.48 0.53 3.AS 0 30 4,!5 0.20 3.19 03') 3 49 0.30 3 05 0.29 3.82 0.02 2.82 0 I3 3 . 75 0.30 2.04 0.03 3.5.5 0.30 2.53 0.07 3.33 0.13 2.38 0.03 3.02 0.40 2.31 0.07
2.86 2.74 2.59 2.4.5 2.32 2.22 2.17 2.10 2.02
0.07 0.07 0.30 0.13 0.07 0.20 0.20 0.20 0.20
d, A. I/I; N3. Cholesterol digitonide 14.09.ct 7.73 6.13
5 2U 4.42 3.87 3.G0 3 34 2 !IP
0.03 0.07 0 03 0.03 0 03
d , A.
d , A.
I/I, @-Sitosterol digitonide 14.0 0.20 11.7 0.01 7.73 0.15 8.63 0.02 7.66 0 I5 7.14 0.10 6.15 1 00 5.72 0.27 0 27 5.04 4.21 0 13 0 20 3.82 0.15 3.60 3.35 0.10 3.05 0.10 2.56 0.03 0.02 2.45 2.11 0.01 2.00 0 01
h-4.
0.40 0.30 0.30 1.00 0.53 0.07 0.13 0.13 0.07 0.07
IV. 0 1 . Gitoxin 13 7 0.20 9.41 0.09 0.36 7.00 6.49 1 .oo 5.79 0.67 B.47 0.49 5.20 0.01 5.05 1.00 4.81 0.01 4.63 0.36 4.34 0.36 4.10 0.36 3 96 0.30 3.78 0 36 3.63 0.36 3.40 0.36 3 26 0.36 0.36 3.19 3.08 0.20 2.95 0.13 2.87 0.13 2.75 0.36 2.69 0.04 2 G3 0.04 2.54 0.09 2 48 0.01 2.41 0.09 2.32 0.09 2 2i 0.01 2.22 0.01 0.27 2.18 2.10 0 01 2 03 0.27 2.02 0.01 0.01 1.97 1.90 0.01 1 sr, 0.09
2,14 2.05 1.97 1.86 1.71
I'I.
S5. A5-Androsten~ benzoate digitonide
13.7 11.2 9.71 7.63 6.92 6.09 5.4g 5.03 4 21 3.87 3.01 3.3n 3 13
'
0.56 0.03 0.38 0.03 0.56 1.00 0.23 1.00 0.56 0.7.5 0.56 0.13 0 13
DIGITALIS GLYCOSIDES
02. 12.0 10.8 8.98 7.17 6.09 5.63 5.29 5.11 4.66 4.43 4.17 3.98 3.78 3.59 3.47 3.32 3.21 3.08 2.90 2.91 2.74 2.59 2.46 2.31 2.23 2 15 2.09 2.05 1.99 1.94 1.90 1.83 1.78 1.74 1.70 1.64
Digoxin
0 13 0 20
0 13 0 36 0 67 0 09 1 00 1 00 0 13 0 36 0 27 0 27 0 13 0 09 0 20 0 02 0 27 0 20 0 13 0 13 0 04 0 20 0 20 0 13 0 13 0 13 0 13 0 13 0 01 0 09 0 13 0 09 0 02 0 09 0 01 0 01
03. 15.0 9 0i 8.01 7.28 7.00 6.26 5.9.5 5.63 5.32 5.00 4.80 4.172 4.32 4.10 3.93 3.73 3.62 3.52 3.39 3.30 3.23 3.06 2.89 2 75 2.60 2.52 2.43 2.37 2.20 2 10 2 0: 2 01 1.95
Digitoxifi 0 07 0 21J 0 0: 0 3'1 0 30 0 '40 1 00 0 53 0 13 0 40 0 40 0 40 0 73 0 30 0 30 0 30 0 07 0 07 0 0: 0 20 0 07 0 07 0 0: 0 0i 0 03 0 02 0 03 0 02 0 02 0 01 0 02 0 0' 0 01
N1.
ACKNOWLEDGMENT
The authors would like to acknowledge the assistanceof XIorioii Smale in the preparation of the x-ray data and photographs. LITERATURE CITED
(1) Haiiawalt, J. D . , R i n n , H. W.,a n d Frevel, L. K., TND. Esc;. CHEY.,-4s.4~.ED.,10, 457 (1935). (2) Klrlg, H. P., a n d Alexander, L. E., "X-Ray Diffraction Proeedures." p. 365, Wiley, Xew York, 1954. (3) Parsons. J.. and Beher, W. T., Aiv.4~.CHEY.,27, 514 (1955.. R F c E i r F n for review M a y 9, 1953.
Accepted J u n e 1. 1955.
