1-Nonanol → 1-Octen-3-Ol

HRID 1490025Notes

Reaction equation

HRID 1490025 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10]([OH:29])(=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\C/C=C\CCCCC.C([OH:39])CCCCCCCC>>[CH2:1]=[CH:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O:39]=[CH:19]/[CH:18]=[CH:17]/[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 89141-NonanolHCID 188271-Octen-3-Ol2×HCID 5280450Linoleic Acid

Product 2

HCID 188271-Octen-3-OlHCID 12431569(8E)-10-Oxo-8-decenoic acid

Procedure

Three mushroom supernatants were made using the method similar to the procedure for 1-octen-3-ol analysis (Mau, (1992)). Mushroom supernatants were prepared by blending 50 g of mushrooms with 100 mL of 0.1M Na phosphate buffer, pH 6.5, and linoleic acid (0, 25.6 and 51.2 mg for supernatants A, B and C, respectively). 1-Nonanol was added as an internal standard prior to blending in order to quantify 1-octen-3-ol. After pentane extraction and centrifugation, the pentane layer was removed for 1-octen-3-ol assay, and the supernatant (ca 135 ml) was adjusted to the final volume of 200 mL using deionized H2O. Due to the fact that 1-octen-3-ol and 10-oxo-trans-8-decenoic acid are formed at the molar ratio of 1:1 (Wurzenberger et al., (1982)), the concentrations of ODA in supernatants were computed directly from the 1-octen-3-ol content to be 2.7×10-5, 4.8×10-4, and 9.4×10-4M for supernatants A, B and C, respectively.

Workup

  1. customMushroom supernatants were prepared
  2. extractionAfter pentane extraction and centrifugation
  3. customthe pentane layer was removed for 1-octen-3-ol assay

Sources & evidence

ORD record
ord-55f6a6bbb0224081b57c2d1a73d47833
Source dataset
uspto-grants-1997_10
Patent number
US05681738

Reaction notes

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