Identification of chlorinated dimethoxystilbene isomers and homologues in bleached paper

J. G. McDonald, R. A. Hites

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

We report here the identification of a novel class of compounds, the chlorinated dimethoxystilbenes (pinosylvins), in bleached paper products. Pinosylvins are naturally occurring compounds in wood that deter infections and predators. These compounds are being chlorinated during the pulp bleaching process. Two dichlorinated pinosylvins have previously been identified in bleached paper pulp, but we have identified other isomers and more highly chlorinated homologues in various bleached paper products. These compounds are present at concentrations on tim order of hundreds of ppb. On the basis of the mass spectra of synthesized standards, we can distingulsh the isomers in which the chlorines are located on the ethylene moiety from those in which the chlorines are located on the aromatic ring with the methoxy groups. In addition, we can predict the chlorine substitution patterns on both rings for these compounds using linear relationships between retention indexes and calculated dipole moments. The toxicity of these compounds is not known; however, isomers related to the pesticide methoxychlor are proestrogenic.

Original languageEnglish (US)
Pages (from-to)4859-4864
Number of pages6
JournalAnalytical Chemistry
Volume72
Issue number20
DOIs
StatePublished - Oct 15 2000

Fingerprint

Chlorine
Isomers
Paper products
Pulp
Methoxychlor
Dipole moment
Bleaching
Pesticides
Toxicity
Wood
Substitution reactions

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

Identification of chlorinated dimethoxystilbene isomers and homologues in bleached paper. / McDonald, J. G.; Hites, R. A.

In: Analytical Chemistry, Vol. 72, No. 20, 15.10.2000, p. 4859-4864.

Research output: Contribution to journalArticle

@article{18cfe465a3eb4bf39ea75b95c3770982,
title = "Identification of chlorinated dimethoxystilbene isomers and homologues in bleached paper",
abstract = "We report here the identification of a novel class of compounds, the chlorinated dimethoxystilbenes (pinosylvins), in bleached paper products. Pinosylvins are naturally occurring compounds in wood that deter infections and predators. These compounds are being chlorinated during the pulp bleaching process. Two dichlorinated pinosylvins have previously been identified in bleached paper pulp, but we have identified other isomers and more highly chlorinated homologues in various bleached paper products. These compounds are present at concentrations on tim order of hundreds of ppb. On the basis of the mass spectra of synthesized standards, we can distingulsh the isomers in which the chlorines are located on the ethylene moiety from those in which the chlorines are located on the aromatic ring with the methoxy groups. In addition, we can predict the chlorine substitution patterns on both rings for these compounds using linear relationships between retention indexes and calculated dipole moments. The toxicity of these compounds is not known; however, isomers related to the pesticide methoxychlor are proestrogenic.",
author = "McDonald, {J. G.} and Hites, {R. A.}",
year = "2000",
month = "10",
day = "15",
doi = "10.1021/ac000474g",
language = "English (US)",
volume = "72",
pages = "4859--4864",
journal = "Analytical Chemistry",
issn = "0003-2700",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

T1 - Identification of chlorinated dimethoxystilbene isomers and homologues in bleached paper

AU - McDonald, J. G.

AU - Hites, R. A.

PY - 2000/10/15

Y1 - 2000/10/15

N2 - We report here the identification of a novel class of compounds, the chlorinated dimethoxystilbenes (pinosylvins), in bleached paper products. Pinosylvins are naturally occurring compounds in wood that deter infections and predators. These compounds are being chlorinated during the pulp bleaching process. Two dichlorinated pinosylvins have previously been identified in bleached paper pulp, but we have identified other isomers and more highly chlorinated homologues in various bleached paper products. These compounds are present at concentrations on tim order of hundreds of ppb. On the basis of the mass spectra of synthesized standards, we can distingulsh the isomers in which the chlorines are located on the ethylene moiety from those in which the chlorines are located on the aromatic ring with the methoxy groups. In addition, we can predict the chlorine substitution patterns on both rings for these compounds using linear relationships between retention indexes and calculated dipole moments. The toxicity of these compounds is not known; however, isomers related to the pesticide methoxychlor are proestrogenic.

AB - We report here the identification of a novel class of compounds, the chlorinated dimethoxystilbenes (pinosylvins), in bleached paper products. Pinosylvins are naturally occurring compounds in wood that deter infections and predators. These compounds are being chlorinated during the pulp bleaching process. Two dichlorinated pinosylvins have previously been identified in bleached paper pulp, but we have identified other isomers and more highly chlorinated homologues in various bleached paper products. These compounds are present at concentrations on tim order of hundreds of ppb. On the basis of the mass spectra of synthesized standards, we can distingulsh the isomers in which the chlorines are located on the ethylene moiety from those in which the chlorines are located on the aromatic ring with the methoxy groups. In addition, we can predict the chlorine substitution patterns on both rings for these compounds using linear relationships between retention indexes and calculated dipole moments. The toxicity of these compounds is not known; however, isomers related to the pesticide methoxychlor are proestrogenic.

UR - http://www.scopus.com/inward/record.url?scp=0034667950&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034667950&partnerID=8YFLogxK

U2 - 10.1021/ac000474g

DO - 10.1021/ac000474g

M3 - Article

C2 - 11055700

AN - SCOPUS:0034667950

VL - 72

SP - 4859

EP - 4864

JO - Analytical Chemistry

JF - Analytical Chemistry

SN - 0003-2700

IS - 20

ER -