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2β,3β,6α,22R,25-PENTAHYDROXY-5β-CHOLESTANE

Year of first isolation: 1988
Formula:C27H48O5
Molecular weight:452
Occurence in plants:
 
Occurence in animals:
Mus musculus [Muridae] » Images of Mus musculus Wikipedia: Mus musculus [Muridae]
2β,3β,6α,22R,25-PENTAHYDROXY-5β-CHOLESTANE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2C1(CCC3C2CC(C4C3(CC(C(C4)O)O)C)O)C)C(CCC(C)(C)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)[C@H](CC1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@@H]([C@@H](CCC(C)(C)O)O)C)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)[C@H](CC1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]([C@@H](CCC(C)(C)O)O)C)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)[C@H](CC1[C@@H]2CC[C@]2([C@@H]1CC[C@@H]2[C@@H]([C@@H](CCC(C)(C)O)O)C)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-[(2S)-3,6-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3,6-triol
CAS-RN 
PubChem CID122639897
InChiKey
[ ChemIDPlus: search ]
XOONVXQOWQKNOJ-IHSXCLGUSA-N
InChIInChI=1S/C27H48O5/c1-15(21(28)9-10-25(2,3)32)17-6-7-18-16-12-22(29)20-13-23(30)24(31)14-27(20,5)19(16)8-11-26(17,18)4/h15-24,28-32H,6-14H2,1-5H3/t15-,16-,17+,18-,19-,20-,21?,22-,23+,24-,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z470 (M+H+NH3)+, 453, 435, 417, 199, 381
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
CD3OD
01-Ha1.45
01-He1.65
02-Ha3.62 (m, w1/2=22)
03-He3.97 (m, w1/2=8)
04-Ha1.62
04-He1.85
05-H1.9
06-Ha4.06 (m, w1/2=21)
07-Ha~1.1
07-He~1.6
09-Ha 
11-Ha 
11-He 
12-Ha1.25
12-He2.05
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H1.5
18-Me0.72 (s )
19-Me0.99 (s )
20-H1.7
21-Me0.94 (d, 6.5)
22-H3.55
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.18 (s )
27-Me1.20 (s )
D2O
01-Ha1.35
01-He1.7
02-Ha3.78
03-He4.04
04-Ha1.7-1.8
04-He1.7-1.8
05-H1.8
06-Ha4.16
07-Ha1.1
07-He1.6
09-Ha 
11-Ha 
11-He 
12-Ha1.25
12-He2.02
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H1.45
18-Me0.68
19-Me0.98
20-H1.7
21-Me0.91
22-H3.64
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.20
27-Me1.21

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
RP-HPLC[ Zorbax-ODS 250 mm x 4.6 mm i.d., solvent linear gradient 18% to 40% (in 30 min) of ACN in 0.1% TFA in H2O, flow-rate 1 ml.min-1] Ret 22.1 min (E : 14.8 min)
NP-HPLC[Zorbax-Sil 250 mm x 4.6 mm i.d., flow-rate 1 ml.min-1] : 1 [solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v] Ret 16.8 min (E : 26 min); 2 [solvent CH2Cl2-iPrOH-H2O 125:20:1.5 v/v/v] Ret 20.9 min (E : 33.8 min); 3 [solvent isoC8-iPrOH-H2O 100:30:2 v/v/v] Ret 21.8 min (E 31.2 min)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationGIRAULT, J.-P. et al. (1988) Drug Metab. Dispos. 16, 716-720 Search more

see Important notice
© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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