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Nicotinic Acid → Diosgenin

HRID 741542
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 741542
Cl[C:2]1[CH:12]=[C:11](Cl)[CH:10]=[CH:9][C:3]=1[O:4]CC(O)=O.[C:14]([OH:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=N[CH:16]=1.[CH3:23][C:24]1[N+](CC2C=NC(C)=NC=2N)=CS[C:25]=1[CH2:38][CH2:39]O.Cl.CC1N=[CH:47][C:46]([CH2:49]O)=[C:45]([CH2:51]O)C=1O.Cl.[C@@H:55]1(O)[C@@H:60](O)[C@H](O)[C@@H](O)[C@@H:57](O)[C@H:56]1O.[C-:67]#[Si+]>Cl.[O-][V]([O-])([O-])=O.[Na+].[Na+].[Na+].[O-][V](=O)=O.[Na+].O[V](O)(O)=O>[CH3:49][C@H:46]1[CH2:47][O:22][C@@:14]2([O:21][C@H:19]3[CH2:18][C@H:60]4[C@@H:55]5[CH2:56][CH:57]=[C:12]6[CH2:2][C@@H:3]([OH:4])[CH2:9][CH2:10][C@:11]6([CH3:67])[C@H:39]5[CH2:38][CH2:25][C@:24]4([CH3:23])[C@H:20]3[C@@H:15]2[CH3:16])[CH2:51][CH2:45]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 6

HCID 938Nicotinic AcidHCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 6019Pyridoxine HydrochlorideHCID 9863Silicon carbideHCID 5745162-[3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;hydrochlorideHCID 178521644HCID 178521644, Verbindung

Produkt

1
HCID 99474DiosgeninAusbeute 0,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 61671Sodium orthovanadateKatalysatorHCID 417214Vanadic acidKatalysatorHCID 4148882Sodium metavanadateKatalysatorHCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Dioscorea deltoides (Mexican yam) cells (about 300-400 mg. fresh weight per flask) were grown in the dark in suspension in a growth medium, as described by Murashige and Skook (Physiol. Plantarum 1962 15: 473), containing 0.1 mg./l. 2,4-dichlorophenoxyacetic acid, 1 mg./l. nicotinic acid, 10 mg./l. thiamine-HCl, 1 mg./l. pyridoxine-HCl and 100 mg./l. inositol, in 125 ml. Erlenmeyer flasks on a rotary shaker (100 rpm, 28° C.). The volume of growth medium per flask was 30 ml., which contained about 10-20 mg. fine mesh carborundum and about 10 mg. sodium orthovanadate. An approximately equimolar amount of sodium metavanadate could be used instead of the orthovanadate. Comparative runs were carried out with and without addition to the medium of elicitor in the form of oxidized BSA (20 μg./ml.). After about 3 weeks, the cells were harvested, lyophilized, refluxed for 2 hours in 2N HCl, filtered, washed with water and dried. The cells were then extracted with chloroform at 60° C., the extract was filtered and evaporated to dryness, and the residue was taken up in chloroform and chromatographed. The spots were visualized with antimony chloride in chloroform. The spots were then dissolved in chloroform and the O.D. read in a spectrophotometer. Some determinations were made by GLC. In absence of elicitor there were obtained 0.1% (dry weight) diosgenin, compared with 3.8% (dry weight) in presence of elicitor, the latter representing a 38 fold enhancement of yield. The dry weight of cells at the end of the run was 1.6 g. per flask.

Aufarbeitung

  1. additioncontaining 0.1 mg
  2. customon a rotary shaker (100 rpm, 28° C.)
  3. customThe volume of growth medium per flask was
  4. additionwithout addition to the medium of elicitor in the form of oxidized BSA (20 μg./ml.)
  5. waitAfter about 3 weeks
  6. filtrationfiltered
  7. washwashed with water
  8. customdried
  9. extractionThe cells were then extracted with chloroform at 60° C.
  10. filtrationthe extract was filtered
  11. customevaporated to dryness
  12. customchromatographed
  13. dissolutionThe spots were then dissolved in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-6819d1bbbf7f45b3ad1c201d339369d8
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05552307

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