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CYASTERONE 22-ACETATE

Year of first isolation: 1978
Formula:C31H46O9
Molecular weight:562
Occurence in plants:
Ajuga turkestanica [Lamiaceae (alt. Labiatae)] » Images of Ajuga turkestanica Wikipedia: Ajuga turkestanica [Lamiaceae (alt. Labiatae)]
Ajuga nipponensis [Lamiaceae (alt. Labiatae)] » Images of Ajuga nipponensis Wikipedia: Ajuga nipponensis [Lamiaceae (alt. Labiatae)]
Ajuga taiwanensis [Lamiaceae (alt. Labiatae)] » Images of Ajuga taiwanensis Wikipedia: Ajuga taiwanensis [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
CYASTERONE 22-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)OC(=O)C
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@](C)([C@@H](C[C@@H]1[C@H](OC(=O)[C@H]1C)C)OC(=O)C)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R,3R)-1-[(2R,3S,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxy-3-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butan-2-yl] acetate
CAS-RN67883-31-2
PubChem CID101355227
InChiKey
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GFPSWBAAJFSDOH-OOTRXCNISA-N
InChIInChI=1S/C31H46O9/c1-15-18(16(2)39-27(15)36)11-26(40-17(3)32)30(6,37)25-8-10-31(38)20-12-22(33)21-13-23(34)24(35)14-28(21,4)19(20)7-9-29(25,31)5/h12,15-16,18-19,21,23-26,34-35,37-38H,7-11,13-14H2,1-6H3/t15-,16+,18-,19-,21-,23+,24-,25-,26+,28+,29+,30+,31+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)544 (M-18; 1), 526 (M -2x18; 2), 516 (M-18-CO; 1), 508 (M-3x18; 1), 498 (M-2x18-CO; 12), 484 (M-AcOH-18; 16), 466 (M-AcOH-2x18; 85), 456 (16), 451 (14), 448 (8), 433 (11), 377 (5), 371 (12), 363 (3), 360 (10), 359 (16), 353 (10), 345 (5), 327 (8), 301 (10), 300 (13), 299 (11), 250 (10), 249 (11), 183 (22), 139 (19), 69 (42), 60 (14), 43 (100).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.9 (t)
0268.1 (d)
0368.0 (d)
0432.0 (t)
0551.3 (d)
06203.3 (s)
07121.9 (d)
08165.5 (s)
0934.3 (d)
1038.7 (s)
1121.5 (t)
1231.8 (t)
1348.2 (s)
1484.1 (s)
1532.4 (t)
1621.0 (t)
1750.3 (d)
1817.8 (q)
1924.4 (q)
2076.1 (s)
2121.2 (q)
2276.8 (d)
2329.9 (t)
2448.0 (d)
2542.7 (d)
26178.7 (s)
2715.6 (q)
2879.2 (d)
2918.9 (q)
CO (AcO)170.8 (s)
Me (AcO)21.7 (q)
C5D5N
01-Ha 
01-Hb 
02-Ha4.05
03-He4.05
04-Ha 
04-He 
05-H 
07-H6.12
09-Ha3.44 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.95
19-Me1.06
21-Me1.47
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me--
27-Me1.21
28-H3.90
29-Me1.32
O-Ac1.94
C5D5N
01-He 
02-Ha4.15 (dm, w1/2 = 25)
03-He4.21 (bs, w1/2 = 9)
04-Ha 
04-He 
05-H3.01 (dd, 12.2, 3.6)
07-H6.26 (d, 2.1)
09-Ha3.58 (bm)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.63 (t, 8.4)
18-Me1.18 (s)
19-Me1.06 (s)
20-H 
21-Me1.57 (s)
22-H5.47 (bd, 10.5)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me 
27-Me1.44 (d, 7.2)
28-H3.96 (dq, 8.7, 6.0)
29-Me1.32 (d, 6.0)

PHYSICAL PROPERTIES

M.P.212-215 °C
[α]D2996 +/- 2 ° (c 0.56 ; MeOH)
IR (KBr) ν max (cm-1)3440 (OH), 1755 (gama-lactone), 1655 (CO)
UV (EtOH) λ max (log ε)240 (4.07)

CHROMATOGRAPHY

HPTLC 
TLC(silica) Rf 0.35 (CHCl3-EtOH 9:1)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationUSMANOV, B.Z. et al. (1978) Khim. Prir. Soedin. 466-470 Search more
GeneralZENG, X.-N et al. (2000) J. Asian Nat. Prod. Res. 2, 263-269 Search more
IdentificationCHAN, Y.-Y. et al. (2005) Chem. Pharm. Bull. 53, 836-838 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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