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MAKISTERONE C 20,22-ACETONIDE

Year of first isolation: 2018
Formula:C32H52O7
Molecular weight:548
Occurence in plants:
Rhaponticum uniflorum [Asteraceae] » Images of Rhaponticum uniflorum Wikipedia: Rhaponticum uniflorum [Asteraceae]
Occurence in animals:
 
MAKISTERONE C 20,22-ACETONIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCCC(CC1C(OC(O1)(C)C)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)C(C)(C)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@H](OC(O1)(C)C)CC(C(C)(C)O)CC)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@H](OC(O1)(C)C)C[C@H](C(C)(C)O)CC)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@H](OC(O1)(C)C)C[C@@H](C(C)(C)O)CC)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(4R,5R)-5-[(2R)-2-ethyl-3-hydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID70682716
InChiKey
[ ChemIDPlus: search ]
BYODBFXLZYKGPR-RINJXUFZSA-N
InChIInChI=1S/C32H52O7/c1-9-18(27(2,3)36)14-26-31(8,39-28(4,5)38-26)25-11-13-32(37)20-15-22(33)21-16-23(34)24(35)17-29(21,6)19(20)10-12-30(25,32)7/h15,18-19,21,23-26,34-37H,9-14,16-17H2,1-8H3/t18-,19+,21+,23-,24+,25+,26-,29-,30-,31-,32-/m1/s1

MASS SPECTRUM

HR-MS
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %) 571 [M+Na]+, 549 [M+H]+

CARBON NMR

PROTON NMR

CD3OD
0137.5
0268.8
0368.3
0432.8
0552.0
06206.2
07121.8
08167.5
0935.0
1039.5
1121.0
1232.3
1349.3
1485.4
1531.4
1621.4
1750.6
1818.2
1924.1
2086.0
2122.4
2281.7
2330.5
2450.1
2574.2
2626.0
2729.3
2825.7
2914.1
Acetonide27.0 (CH3), 29.1 (CH3), 108.2 (C)
CD3OD
01-Ha1.43 (dd, 13.2, 12.0)
01-He1.85 (dd, 13.2, 4.4)
02-Ha3.82 (ddd, 12.0, 4.4, 2.8)
03-He4.18 (m)
04-Ha1.60-1.63 (m)
04-He1.72-1.73 (m)
05-H2.41 (dd; 12.2, 5.4)
07-H5.95 (d, 2.5)
09-H3.19 (ddd, 12/1, 7.0, 2.5)
11-Ha1.64-1.66 (m)
11-He1.80-1.82 (m)
12-Ha2.15 (ddd, 13.1, 12.8, 5.4)
12-He1.85-1.87 (m)
15-Ha1.53-1.55 (m)
15-Hb2.03-2.06 (m)
16-Ha1.98-2.00 (m)
16-Hb1.74)-1.75 (m)
17-H2.44 (m)
18-Me0.88 (s)
19-Me0.96 (s)
21-Me1.19 (s)
22-H3.95 (dd, 8.4, 3.0)
23-Ha1.12-1.17 (m)
23-Hb1.75-1.79 (m)
24-H1.47 (ddd, 12.3, 6.3, 2.8)
26-Me1.23 (s)
27-Me1.09 (s)
28-Ha1.24-127 (m)
28-Hb1.68-1.71 (m)
29-Me1.01 (t, 7.1)
Methyls1.30 (s), 1.33 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)242 nm () ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationOLENNIKOV, D.N. et al. (2018) Chem. Nat. Compd. 54 (5), 930-933 Search more

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© 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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