Welcome to online ecdysteroids database ! . .
Access data · History · Contact

AJUGASTERONE C 20,22-MONOACETONIDE

Year of first isolation: 1992
Formula:C30H48O7
Molecular weight:520
Occurence in plants:
Vitex strickeri [Lamiaceae (alt. Labiatae)] » Images of Vitex strickeri Wikipedia: Vitex strickeri [Lamiaceae (alt. Labiatae)]
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
AJUGASTERONE C 20,22-MONOACETONIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC1C(OC(O1)(C)C)(C)C2CCC3(C2(CC(C4C3=CC(=O)C5C4(CC(C(C5)O)O)C)O)C)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@@H](CCC(C)C)OC(O1)(C)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(4R,5R)-2,2,4-trimethyl-5-(3-methylbutyl)-1,3-dioxolan-4-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID12044243
InChiKey
[ ChemIDPlus: search ]
HNFIAGLFDMBJTE-DISVCFHPSA-N
InChIInChI=1S/C30H48O7/c1-16(2)8-9-24-29(7,37-26(3,4)36-24)23-10-11-30(35)18-13-19(31)17-12-20(32)21(33)14-27(17,5)25(18)22(34)15-28(23,30)6/h13,16-17,20-25,32-35H,8-12,14-15H2,1-7H3/t17-,20+,21-,22+,23-,24+,25+,27-,28+,29+,30+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)520 (M)+ (10), 505 (20), 502 (5), 487 (10), 469 (4), 462 (98), 445 (20), 444 (28), 427 (33), 426 (32), 420 (33), 411 10), 409 (20), 402 (13), 379 (20), 361 (17), 299 (12), 281 (7), 266 (33), 185 (100), 142 (58), 127 (83), 114 (33), 109 (33), 84 (60).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.01
0268.15
0368.39
0432.88
0552.46
06203.80
07122.42
08163.80
0942.76
1039.88
1168.71
1243.87
1347.88
1484.21
1531.78
1622.18
1749.81
1818.27
1924.81
2082.01
2122.27
2284.88
2329.38
2436.88
2528.26
2622.45
2722.81
Me27.14, 27.14
O-C-O106.92
C5D5N
01-Ha2.00 (d, 12)
01-He3.42 (dd, 5, 12)
02-Ha4.52
03-He4.21 (d, 4)
04-Ha1.78 (ddd, 4, 14, 14)
04-He2.03 (dt, 4, 4, 4, 14)
05-H3.04 (dd, 4, 14)
07-H6.29 (d, 5)
09-Ha3.82
11-Ha4.57
12-Ha2.95 (dd, 12, 12)
12-He2.57 (dd, 12, 7)
15-Ha1.95
15-Hb2.19
16-Ha2.13
16-Hb2.23
17-H2.79 (dd, 8, 8)
18-Me1.31 (s )
19-Me1.32 (s )
21-Me1.08 (s )
22-H3.86
23-Ha1.55
23-Hb1.39
24-Ha1.55
24-Hb1.50
25-H1.46
26-Me0.81 (d, 8)
27-Me0.81 (d, 8)
Me-ketals1.52, 1.46

PHYSICAL PROPERTIES

M.P.246-249 °C (or 287-288 °C)
[α]D20 
IR (Nujol) ν max (cm-1)3200 (OH), 1650 (cyclohexenone); ( KBr) 3400-3440(OH), 1675
UV (MeOH) λ max (log ε)237 (?)

CHROMATOGRAPHY

TLC 
RLCCsolvent system H2O-EtOAc-n-PrOH (6:6:1)
GLC 
HPLCRecycle RP-HPLC, column Asahipack GS-320 (50 x 2 cm i.d.) solvent MeOH, flow-rate 3.5 ml.min-1.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZHANG, M. et al. (1992) Phytochemistry 31, 247-250 Search more
First isolationMULADEVA, K. et al. (1992) Khim. Prir. Soedin., 71-76 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE