Reaktion #429240

ord-85aedc71c386482c846211f30d43cde3

Reaktionsgleichung

C/C=C(\C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C(=O)OC)CO[C@H]3[C@@H](O)[C@@](C)([C@]45O[C@@]4(C)[C@@H]4C[C@H]5O[C@@H]5OC=C[C@@]54O)[C@H]4[C@]1(CO[C@]4(O)C(=O)OC)[C@@H]32
azadirachtin A
→
C/C=C(\C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C(=O)OC)CO[C@H]3[C@@H](O)[C@@](C)([C@]45O[C@@]4(C)[C@H]4C[C@@H]5O[C@@H]5OC=C[C@@]54O)[C@H]4[C@]1(CO[C@]4(O)C(=O)OC)[C@@H]32
azadirachtin
Ausbeute 25.0%

Edukte

C/C=C(\C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C(=O)OC)CO[C@H]3[C@@H](O)[C@@](C)([C@]45O[C@@]4(C)[C@@H]4C[C@H]5O[C@@H]5OC=C[C@@]54O)[C@H]4[C@]1(CO[C@]4(O)C(=O)OC)[C@@H]32
azadirachtin A
—
( 1 )

Reagenzien

Keine

Lösungsmittel

CCCCCC
hexane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktion(2), extraction of defatted powdered neem kernels
  2. 2
    Temperaturwith refluxing 95% ethanol (a), (1 1.) and (b), (0.5 1.), (3)
  3. 3
    Sonstigepartition of ethanol
  4. 4
    Einengenconcentrate (95 g.)
  5. 5
    Sonstigeobtained
  6. 6
    Sonstigeafter removal of solvent
  7. 7
    Extraktionextract
  8. 8
    workup.DISSOLUTIONdissolved in 90% methanol with petroleum ether (100 ml.) thrice
  9. 9
    Sonstige(4), treatment of residue after removal of solvent from methanol
  10. 10
    Extraktionextract from step 3, with ethylacetate
  11. 11
    Waschen(5), washing of ethylacetate
  12. 12
    Extraktionextract with water
  13. 13
    Sonstigeto remove proteins, carbohydrates
  14. 14
    Sonstige(6), removal of solvent from ethylacetate
  15. 15
    Extraktionextract

Vorschrift

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.).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05856526uspto-grants-1999_01