HCID 44584063, compound → Azadirachtin

HRID 342058Notes

Reaction equation

HRID 342058 reaction equation
[CH3:1]/[CH:2]=[C:3](/[C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][C@@H:26]5[CH2:27]4)[O:35][CH:34]=[CH:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([O:48][C:49]([CH3:51])=[O:50])[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])\[CH3:4]>CCCCCC>[CH3:1]/[CH:2]=[C:3](/[C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][C@H:26]5[CH2:27]4)[O:35][CH:34]=[CH:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([O:48][C:49]([CH3:51])=[O:50])[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])\[CH3:4]

Participants

3

Reactant 1

HCID 44584063HCID 44584063, compound

Product 1

HCID 5281303AzadirachtinYield 25%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Govindachari, Sandhya and Ganeshraj (Govindachari, T. R., Sandhya, G, and Ganeshraj, S. P., Chromatographia, 31, 303, 1991) have prepared azadirachtin A involving the following steps; (1), defatting of powdered neem seed kernels (1 kg.) with hexane (31.); (2), extraction of defatted powdered neem kernels with refluxing 95% ethanol (a), (1 1.) and (b), (0.5 1.), (3), partition of ethanol concentrate (95 g.) obtained after removal of solvent from combined ethanol extract dissolved in 90% methanol with petroleum ether (100 ml.) thrice; (4), treatment of residue after removal of solvent from methanol extract from step 3, with ethylacetate; (5), washing of ethylacetate extract with water to remove proteins, carbohydrates; (6), removal of solvent from ethylacetate extract to give azadirachtin (25%, 24.5 g.); (7), preparative HPLC of azadirachtin (25%, 4 g.) on RP 18 column to give azadirachtin A+D (340 mg.); (8), preparative HPLC of azadirachtin A+D to give azadirachtin A (160 mg.).

Workup

  1. extraction(2), extraction of defatted powdered neem kernels
  2. temperaturewith refluxing 95% ethanol (a), (1 1.) and (b), (0.5 1.), (3)
  3. custompartition of ethanol
  4. concentrationconcentrate (95 g.)
  5. customobtained
  6. customafter removal of solvent
  7. extractionextract
  8. dissolutiondissolved in 90% methanol with petroleum ether (100 ml.) thrice
  9. custom(4), treatment of residue after removal of solvent from methanol
  10. extractionextract from step 3, with ethylacetate
  11. wash(5), washing of ethylacetate
  12. extractionextract with water
  13. customto remove proteins, carbohydrates
  14. custom(6), removal of solvent from ethylacetate
  15. extractionextract

Sources & evidence

ORD record
ord-85aedc71c386482c846211f30d43cde3
Source dataset
uspto-grants-1999_01
Patent number
US05856526

Reaction notes

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