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STACHYSTERONE A

Year of first isolation: 1970
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Stachyurus praecox [Stachyuraceae] » Images of Stachyurus praecox Wikipedia: <br />
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Occurence in animals:
 
STACHYSTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC(C1=CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C(C)(C(CCC(C)(C)O)O)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=C2[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,14S,17S)-2,3-dihydroxy-10,14-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN30655-78-8
PubChem CID24984906
InChiKey
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DSUMGVHMUUADBM-VXUDCIMKSA-N
InChIInChI=1S/C27H42O6/c1-24(2,32)10-9-23(31)27(5,33)17-8-11-25(3)15(17)6-7-16-18(25)12-20(28)19-13-21(29)22(30)14-26(16,19)4/h6,12,16-17,19,21-23,29-33H,7-11,13-14H2,1-5H3/t16-,17-,19-,21+,22-,23+,25-,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)462 (M)+; 426 (M - 2x18)+, 345 (M- C22-C27)+ (9), 327 (4), 143 (C20-C27)+ (96), 125 (34), 99 (C22-C27)+ (20), 81 (28), 43 (100).
HR-MS426.2699 (for C27H38O4, calc. 426.2769)

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 
C5D5N
01-Ha 
01-He 
02-Ha4.09 (m, w1/2=22)
03-He4.31 (m, w1/2=8)
04-Ha 
04-He 
05-H 
07-H6.14 (d, 2.5)
09-Ha 
11-Ha 
11-He 
12-H5.98 (m )
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me--
19-Me0.92 (s )
21-Me1.51 (s )
22-H3.85 (m )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.41 (s )
27-Me1.41 (s )
Other14-Me1.20 (s )
CDCl3 (2,3,22-OAc)
01-Ha 
01-He 
02-Ha4.90-5.10 (m )
03-He5.35 (m, w1/2=7.5)
04-Ha 
04-He 
05-H2.37 (dd, 13, 5)
07-H5.93 (d, 2.5)
09-Ha 
11-Ha 
11-He 
12-H6.04 (m )
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me--
19-Me0.98 (s )
21-Me1.30 (s )
22-H4.90-5.10 (m )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.20 (s )
27-Me1.20 (s )
Other14-Me1.15 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3400 (OH), 1640 (cyclohexenone), 1590
UV (EtOH) λ max (log ε)248 (4.029)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationIMAI, S. et al. (1970) J. Am. Chem. Soc. 92, 7510-7512 Search more

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© Universit√© 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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