Metabolites from the biodegradation of 1,6-hexanediol dibenzoate, a potential green plasticizer, by Rhodococcus rhodochrous

J Mass Spectrom. 2009 May;44(5):662-71. doi: 10.1002/jms.1541.

Abstract

Metabolites from the biodegradation of a potential plasticizer 1,6-hexanediol dibenzoate in the presence of n-hexadecane as a co-substrate by the common soil organism Rhodococcus rhodochrous were identified using GC/MS and Fourier transform mass spectroscopy (FTMS) techniques. Trimethylsilylation of compounds from the biodegradation broth permitted detection of the following metabolites: 1-hexadecyl benzoate, 6-benzoyloxyhexanoic acid, 4-benzoyloxybutanoic acid, 6-benzoyloxyhexan-1-ol and benzoic acid. The presence of these metabolites was confirmed by repeating the biodegradation with 1,6-hexanediol di[(2)H(5)]benzoate, by measurement of their exact masses in FTMS and by comparison with available authentic materials. The results show that biodegradation of 1,6-hexanediol dibenzoate by R. rhodochrous does not lead to the accumulation of persistent metabolites as has been reported for commercial dibenzoate plasticizers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoates / chemistry
  • Benzoates / metabolism*
  • Biodegradation, Environmental*
  • Fourier Analysis
  • Gas Chromatography-Mass Spectrometry
  • Green Chemistry Technology / methods
  • Mass Spectrometry
  • Nuclear Magnetic Resonance, Biomolecular
  • Plasticizers / chemistry
  • Plasticizers / metabolism*
  • Rhodococcus / metabolism*

Substances

  • 1,6-hexanediol dibenzoate
  • Benzoates
  • Plasticizers