An inositol → An inositol

HRID 2297369Notes

Reaction equation

HRID 2297369 reaction equation
[CH:1]1([OH:12])[CH:6]([OH:7])[CH:5]([OH:8])[CH:4]([OH:9])[CH:3]([OH:10])[CH:2]1[OH:11].[CH2:13]([OH:35])[C@H:14]1[O:19][C@H:18]([O:20][CH:21]2[C@@H:26]([OH:27])[C@@H:25]([OH:28])[CH:24]([OH:29])[C@H:23]([OH:30])[C@H:22]2[OH:31])[C@H:17]([OH:32])[C@@H:16]([OH:33])[C@H:15]1[OH:34].[CH2:36]([OH:58])[C@H:37]1[O:42][C@H:41]([O:43][CH:44]2[C@@H:49]([OH:50])[C@H:48]([OH:51])[CH:47]([OH:52])[C@@H:46]([OH:53])[C@@H:45]2[OH:54])[C@H:40]([OH:55])[C@@H:39]([OH:56])[C@H:38]1[OH:57]>>[O:7]=[CH:6][C@@H:5]([C@H:4]([C@H:3]([C@@H:2]([CH2:1][OH:12])[OH:11])[OH:10])[OH:9])[OH:8].[CH:21]1([OH:20])[CH:22]([OH:31])[CH:23]([OH:30])[CH:24]([OH:29])[CH:25]([OH:28])[CH:26]1[OH:27].[CH2:36]([OH:58])[C@H:37]1[O:42][C@H:41]([O:43][CH:44]2[C@@H:45]([OH:54])[C@@H:46]([OH:53])[CH:47]([OH:52])[C@H:48]([OH:51])[C@H:49]2[OH:50])[C@H:40]([OH:55])[C@@H:39]([OH:56])[C@H:38]1[OH:57].[CH2:13]([OH:35])[C@H:14]1[O:19][C@H:18]([O:12][CH:1]2[C@@H:2]([OH:11])[C@H:3]([OH:10])[CH:4]([OH:9])[C@@H:5]([OH:8])[C@@H:6]2[OH:7])[C@H:17]([OH:32])[C@@H:16]([OH:33])[C@H:15]1[OH:34]

Participants

7

Reactant 3

HCID 892An inositol2×HCID 9840967209287-65-0HCID 9906026HCID 9906026, compound

Product 4

HCID 892An inositolHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 9840967209287-65-0HCID 9906026HCID 9906026, compound

Procedure

Results. Buckwheat bran was extracted with 50% EtOH, and the resulting extract chromatographed on carbon-Celite, 1:1 (w/w), to purify Fagopyritol A1. Fagopyritol B1 was also purified from the same sample for comparison. Per(pentafluoropropionates) of chiro-inositol from acid hydrolysis of Fagopyritol A1 and Fagopyritol B1 co-chromatographed on a chiral column with authentic D-chiro-inositol, but not with authentic L-chiro-inositol. Hydrolysis of Fagopyritol A1 and Fagopyritol B1 produced D-galactose and D-chiro-inositol in mole ratios of 1.01:1.00 for Fagopyritol A1 and 1.03:1.00 for Fagopyritol B1. Free D-chiro-inositol was obtained by acid hydrolysis of a mixture of Fagopyritol A1 and Fagopyritol B1 followed by purification on a carbon-Celite column. Fagopyritol A1 and Fagopyritol B1 were hydrolyzed by α-D-galactosidase, but not by β-D-galactosidase, demonstrating an α-D-galactopyranosyl linkage.

Workup

  1. customResults
  2. extractionBuckwheat bran was extracted with 50% EtOH
  3. extractionthe resulting extract
  4. customchromatographed on carbon-Celite, 1:1 (w/w)
  5. customto purify Fagopyritol A1
  6. customFagopyritol B1 was also purified from the same sample for comparison
  7. customPer(pentafluoropropionates) of chiro-inositol from acid hydrolysis of Fagopyritol A1 and Fagopyritol B1

Sources & evidence

ORD record
ord-8be8e532ef6c406dab01320870b2fe42
Source dataset
uspto-grants-2002_12
Patent number
US06492341B1

Reaction notes

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