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Hydrochloric Acid → Ursodeoxycholic Acid

HRID 1659375
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1659375
C(S)C([O-])=O.[OH:6][C@@H:7]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@H:9]([CH2:10][C@@H:11]([OH:33])[C@@H:12]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:8]1.Cl>>[OH:6][C@@H:7]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@H:9]([CH2:10][C@H:11]([OH:33])[C@@H:12]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:8]1
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Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 10133Chenodeoxycholic AcidHCID 5086465Acetic acid, mercapto-, ion(1-)2×

Produkt 1

HCID 31401Ursodeoxycholic AcidAusbeute 70 %

Versuchsvorschrift

The organism Clostridium absonum (VPI 6903A) is maintained in a chopped meat culture at 4° C. A volume of 1 ml. taken from this chopped meat starter culture is introduced into a 40 ml. volume of freshly autoclaved brain-heart infusion (Barto Brain Heart Infusion B37, Difco Laboratories) broth containing 0.1% thioglycollate. The culture is grown for 12 hours at 37° C., after which it is transferred into 1.0 liter of brain-heart infusion broth containing 0.1% thioglycollate and 5×10-4M 3α, 7α-dihydroxy-5β-cholanoic acid (Chenodeoxycholic Acid). The resultant culture is allowed to grow for 12 hours at 37° C., at which time it is then acidified to pH 3 with HCl and extracted three times with ether. The combined ether extracts were then washed with water, dried over sodium sulfate and evaporated to dryness in vacuo to yield 160 mg of 3α, 7β-dihydroxy-5β-cholanoic acid (yield by thin layer chromatography=70-80%).

Aufarbeitung

  1. additionis introduced into a 40 ml
  2. waitto grow for 12 hours at 37° C., at which time it
  3. extractionextracted three times with ether
  4. washThe combined ether extracts were then washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d760f4d6d59444bfb7afeae556918251
Quelldatensatz
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04303754

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