98767-45-4 → 3-[9-(5-{1,4-Dihydroxy-4-[5-(1-hydroxyundecyl)oxolan-2-yl]butyl}oxolan-2-yl)-2-hydroxynonyl]-5-methylfuran-2(5H)-one

HRID 1611921Notes

Reaction equation

HRID 1611921 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([OH:44])[C@@H:12]1[O:16][C@@H:15]([C@@H:17]2[O:21][C@@H:20]([C@H:22]([OH:43])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C@@H:33]([OH:42])[CH2:34][C:35]3[C:39](=[O:40])[O:38][C@@H:37]([CH3:41])[CH:36]=3)[CH2:19][CH2:18]2)[CH2:14][CH2:13]1.CCCCCCCCCCC(O)C1[O:60]C(C2OC(C(O)CCCCCCCCCCCCC3C(=O)OC(C)C=3)CC2)CC1.CCCCC[C@@H](O)CCCC[C@H](O)[C@@H]1O[C@@H]([C@@H]2O[C@@H]([C@H](O)CCCCCCCCCCCCC3C(=O)O[C@@H](C)C=3)CC2)CC1.CCCCCCC(O)CCCC(O)C1OC(C2OC(C(O)CCCCCCCCCCC3C(=O)OC(C)C=3)CC2)CC1.CCCCCC[C@@H](O)CCC[C@H](O)[C@H]1O[C@H]([C@H](O)CC[C@@H](O)[C@H]2O[C@H](CCCCCCCCCC3C(=O)O[C@H](C)C=3)CC2)CC1.CCCCCCCCCC[C@H](O)[C@@H]1O[C@@H]([C@H](O)CC[C@H](O)[C@H]2O[C@H](CCCCCCC[C@@H](O)CC3C(=O)O[C@@H](C)C=3)CC2)CC1.CCCCCC[C@@H](O)CCC[C@@H](O)[C@H]1O[C@H]([C@H](O)CC[C@@H](O)[C@H]2O[C@H](CCCCCCCCCC3C(=O)O[C@H](C)C=3)CC2)CC1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:44])[CH:12]1[O:16][CH:15]([CH:17]([OH:21])[CH2:18][CH2:19][CH:20]([OH:60])[CH:22]2[O:43][CH:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]([OH:42])[CH2:34][C:35]3[C:39](=[O:40])[O:38][CH:37]([CH3:41])[CH:36]=3)[CH2:24][CH2:23]2)[CH2:14][CH2:13]1

Participants

7

Reactant 6

HCID 46166798767-45-4HCID 10627323159934-23-3HCID 11124994BullatacinHCID 44591858HCID 44591858, compoundHCID 101240443HCID 101240443, compoundHCID 131725265HCID 131725265, compound

Product 1

HCID 1329423-[9-(5-{1,4-Dihydroxy-4-[5-(1-hydroxyundecyl)oxolan-2-yl]butyl}oxolan-2-yl)-2-hydroxynonyl]-5-methylfuran-2(5H)-one

Procedure

The present invention relates to a novel compound designated as isosquamocin (1) and exhibiting insecticidal property. The invention also provides insecticidal composition containing isosquamocin (1), and related compounds squamocin-G (2), asimicin/squamocin-H (3); 4-deoxyasimicin/squamocin-M (4); desacetyluvaracin/squamocin L (5); motrilin/annonin-II/squamocin-C (6); neoannonin/squamocin-J (7); squamocin-K (8), squamocin-B (9), squamostatin-A (10); bullatalicin/squamostatin-B (11); bullatanocin/squamostatin-C/Annonin-V/Cherimolin-II (12) and unidentified compounds with retention times 5.88 min, 14.18 min and 45.25 min in HPLC, all obtained from the plant Annona squamosa. The present invention also provides methods for isolation of isosquamocin (1) and related compounds squamocin-G (2), asimicin/squamocin-H (3); 4-deoxyasimicin/squamocin-M (4); desacetyluvaracin/squamocin L (5); motrilin/annonin-II/squamocin-C (6); neoannonin/squamocin-J (7); squamocin-K (8), squamocin-B (9), squamostatin-A (10); bullatalicin/squamostatin-B (11); bullatanocin/squamostatin-C/Annonin-V/Cherimolin-II (12) and unidentified compounds with retention times 5.88 min, 14.18 min and 45.25 min in HPLC from the extract of the seeds of Annona squamosa. The present invention is also related to the preparation of emulsifiable concentrate formulations of the extract of seeds of Annona squamosa standardized and enriched with respect to isosquamocin for insecticidal applications. The composition of the extract of the seeds of Annona squamosa standardized with respect to isosquamocin and its formulation of the present invention are represented by the FIGS. (13) and (14) showing their analyses by HPLC. Compounds (1) to (12) described in the present invention were characterized by their physical data, optical rotation, CD spectra, 1HNMR spectra, 13CNMR spectra and mass spectra.

Sources & evidence

ORD record
ord-d5110f2127be4d259325bee8ec7032c8
Source dataset
uspto-grants-2006_01
Patent number
US06991818B2

Reaction notes

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