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Year of first isolation: |
1978 |
| Formula: | C31H46O9 |
| Molecular weight: | 562 |
| Occurence in plants: |
Ajuga turkestanica [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga turkestanica [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Ajuga nipponensis [Lamiaceae (alt. Labiatae)] »
Ajuga taiwanensis [Lamiaceae (alt. Labiatae)] »
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| Canonical SMILES | CC1C(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
[ PubChem: search | XML ]
[ ChemSpider: search ] | 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 » 
| | 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-RN | 67883-31-2 | | PubChem CID | 101355227 | InChiKey
[ ChemIDPlus: search ] | GFPSWBAAJFSDOH-OOTRXCNISA-N | | InChI | InChI=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 |
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| 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 | |
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| C5D5N | | 01 | 37.9 (t) | | 02 | 68.1 (d) | | 03 | 68.0 (d) | | 04 | 32.0 (t) | | 05 | 51.3 (d) | | 06 | 203.3 (s) | | 07 | 121.9 (d) | | 08 | 165.5 (s) | | 09 | 34.3 (d) | | 10 | 38.7 (s) | | 11 | 21.5 (t) | | 12 | 31.8 (t) | | 13 | 48.2 (s) | | 14 | 84.1 (s) | | 15 | 32.4 (t) | | 16 | 21.0 (t) | | 17 | 50.3 (d) | | 18 | 17.8 (q) | | 19 | 24.4 (q) | | 20 | 76.1 (s) | | 21 | 21.2 (q) | | 22 | 76.8 (d) | | 23 | 29.9 (t) | | 24 | 48.0 (d) | | 25 | 42.7 (d) | | 26 | 178.7 (s) | | 27 | 15.6 (q) | | 28 | 79.2 (d) | | 29 | 18.9 (q) | | CO (AcO) | 170.8 (s) | | Me (AcO) | 21.7 (q) |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.05 | | 03-He | 4.05 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.12 | | 09-Ha | 3.44 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.95 | | 19-Me | 1.06 | | 21-Me | 1.47 | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | -- | | 27-Me | 1.21 | | 28-H | 3.90 | | 29-Me | 1.32 | | O-Ac | 1.94 |
| C5D5N | | 01-He | | | 02-Ha | 4.15 (dm, w1/2 = 25) | | 03-He | 4.21 (bs, w1/2 = 9) | | 04-Ha | | | 04-He | | | 05-H | 3.01 (dd, 12.2, 3.6) | | 07-H | 6.26 (d, 2.1) | | 09-Ha | 3.58 (bm) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.63 (t, 8.4) | | 18-Me | 1.18 (s) | | 19-Me | 1.06 (s) | | 20-H | | | 21-Me | 1.57 (s) | | 22-H | 5.47 (bd, 10.5) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | | | 27-Me | 1.44 (d, 7.2) | | 28-H | 3.96 (dq, 8.7, 6.0) | | 29-Me | 1.32 (d, 6.0) |
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| M.P. | 212-215 °C | | [α]D29 | 96 +/- 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) |
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| HPTLC | | | TLC | (silica) Rf 0.35 (CHCl3-EtOH 9:1) | | GLC | | | HPLC | |
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Permanent link to this datasheet: CYASTERONE 22-ACETATE
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