7-HYDROXYHEPTANOIC ACID Chemical Properties

Melting point:

46 °C

Boiling point:

145-152 °C(Press: 18 Torr)

Density 

1.073±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Sparingly), Methanol (Sparingly), Water

form 

Solid

pka

4.76±0.10(Predicted)

color 

Colourless to Light Brown

InChI

InChI=1S/C7H14O3/c8-6-4-2-1-3-5-7(9)10/h8H,1-6H2,(H,9,10)

InChIKey

PNAJBOZYCFSQDJ-UHFFFAOYSA-N

SMILES

C(O)(=O)CCCCCCO

7-HYDROXYHEPTANOIC ACID Usage And Synthesis

Uses

7-Hydroxyheptanoic Acid is used as a reagent in the preparation of polymer-supported stannols and distannoxanes. As well it is used in the synthesis of (S)-curvularin, and anti-inflammatory compound.

Definition

ChEBI: An omega-hydroxy fatty acid comprising heptanoic acid which is substituted by a hydroxy group at position 7.

Synthesis

The general procedure for the synthesis of 7-hydroxyheptanoic acid from 7-octen-1-ol was as follows: a solution of 7-octen-1-ol (1 mL, 0.88 g, 6.66 mmol, 1 eq.) in MeCN (15.8 mL, 18 mL/g) and H2O (1.8 mL, 2 mL/g) was added to a reaction vial. The reaction mixture was cooled to 0 °C and ozone was passed at a rate of 12 h at room temperature. The reaction was carried out under the protection of nitrogen at 1 atm. Subsequently, a NaHSO3 solution was prepared by dissolving Na2S2O5 (2.77 g, 14.58 mmol, 2.19 eq.) in H2O (14 mL) and this solution was slowly added to the reaction mixture, keeping the internal temperature below 35°C. After the addition was completed, the mixture was stirred for 10 minutes. EtOAc (10 mL) was added to the reaction mixture and the organic and aqueous layers were separated. The aqueous layer was further extracted with EtOAc, and all the organic layers were combined, dried with MgSO4, filtered and concentrated to give the colorless oily product 7-hydroxyheptanoic acid (0.95 g, 95% yield).

References

[1] Synlett, 2016, vol. 27, # 2, p. 245 - 248

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