Monograph on the Potential Human Reproductive and ... - OEHHA

158 CHAPIN ET AL.
the CERHR Core Committee 2 and will be made available
to the public for comment.
Following the public comment period, CERHR will
prepare the NTP-CERHR <strong>Monograph</strong> on the Potential
Human Reproductive and Developmental Effects of
Bisphenol A. This monograph will include the NTP
Brief, the Expert Panel Report, and all public comments
received on the Expert Panel Report. The NTP-CERHR
<strong>Monograph</strong> will be made publicly available and transmitted
to appropriate health and regulatory agencies.
Reports can be obtained from the web site (http://
cerhr.niehs.nih.gov) or from: Michael D. Shelby, PhD,
NIEHS EC-32, PO Box 12233, Research Triangle Park, NC
27709. E-mail: shelby@niehs.nih.gov
1.0 CHEMISTRY, USE AND HUMAN
EXPOSURE
1.1 Chemistry
Section 1 is based initially on secondary review
sources. Primary study reports are addressed by the
Expert Panel if they contain information that is highly
relevant for determining the effect of exposure on
developmental or reproductive toxicity or if the studies
were released subsequent to the reviews.
1.1.1 Nomenclature. The CAS RN for bisphenol A
is 80-05-7. Synonyms for bisphenol A listed in Chem
IDplus (ChemIDplus, 2006) include: 2-(4,4 0 -Dihydroxydiphenyl)propane;
2,2-Bis(4-hydroxyphenyl)propane;
2,2-Bis(hydroxyphenyl)propane; 2,2-Bis(p-hydroxyphenyl)propane;
2,2-Bis-4 0 -hydroxyfenylpropan [Czech];
2,2-Di(4-hydroxyphenyl)propane; 2,2-Di(4-phenylol)propane;
4,4 0 -(1-Methylethylidene)bisphenol; 4,4 0 -Bisphenol
A; 4,4 0 -Dihydroxydiphenyl-2,2-propane; 4,4 0 -Dihydroxydiphenyldimethylmethane;
4,4 0 -Dihydroxydiphenylpro­
2 The Core Committee is an advisory body consisting of scientists from
government agencies. Agencies currently represented are: Environmental
Protection Agency, Centers for Disease Control and Prevention, Food and
Drug Administration, Consumer Product Safety Commission, National
Institute for Occupational Safety and Health, and National Institute of
Environmental Health Sciences.
Prepared with the Support of CERHR Staff: NTP/NIEHS, Michael D.
Shelby, Ph.D. (Director, CERHR), Paul M.D. Foster, Ph.D. (Deputy
Director, CERHR), Kristina Thayer, Ph.D. (CERHR), Diane Spencer, M.S.
(CERHR), John Bucher, Ph.D. (Associate Director, NTP), Allen Dearry,
Ph.D. (Interim Associate Director, NTP), Mary Wolfe, Ph.D. (Director, NTP
Office of Liaison, Policy & Review), Denise Lasko (NTP Office of Liaison,
Policy & Review); Sciences International, Inc., Anthony Scialli, M.D.
(Principal Scientist), Annette Iannucci, M.S. (Toxicologist), Gloria Jahnke,
D.V.M. (Toxicologist), and Vera Jurgenson, M.S. (Research Assistant).
This report is prepared according to the Guidelines for CERHR Panel
Members established by NTP/NIEHS. The guidelines are available from the
CERHR web site (http://cerhr.niehs.nih.gov/). The format for this report
follows that of CERHR Expert Panel Reports including synopses of studies
reviewed, and an evaluation of the Strengths/Weaknesses and Utility
(Adequacy) of the study for a CERHR evaluation. Statements and
conclusions made under Strengths/Weaknesses and Utility evaluations
are those of the expert panel members and are prepared according to the
NTP/NIEHS guidelines. In addition, the report includes comments or
notes limitations of the study in the synopses. Bold, square brackets are
used to enclose such statements. As discussed in the guidelines, square
brackets are used to enclose key items of information not provided in a
publication, limitations noted in the study, conclusions that differ from
authors, and conversions or analyses of data conducted by CERHR.
The findings and conclusions of this report are those of the Expert
Panel and should not be construed to represent the views of the
National Toxicology Program. Members of this panel participated in
the evaluation of bisphenol A as independent scientists. The findings
and conclusions in this report are those of the authors and do not
necessarily represent the views of their employers.
pane; 4,40-Isopropylidene diphenol; 4,40-Isopropylidene bisphenol; 4,40-Isopropylidene diphenol; Biphenol A;
Bis(4-hydroxyphenyl) dimethylmethane; Bis(4-hydroxyphenyl)dimethylmethane;
Bis(4-hydroxyphenyl)propane;
Bisferol A [Czech]; Bisphenol. Bisphenol A; DIAN; Diano;
Dimethyl bis(p-hydroxyphenyl)methane; Dimethylbis
(p-hydroxyphenyl)methane; Dimethylmethylene-p,p0­ diphenol; Diphenylolpropane; Ipognox 88; Isopropylidenebis(4-hydroxybenzene);
Parabis A, Phenol; (1-methylethylidene)bis-,
Phenol; 4,40-(1-methylethylidene)bis-; Phenol, 4,40-dimethylmethylenedi-; Phenol, 4,40-isopropy lidenedi-; Pluracol 245, Propane; 2,2-bis(p-hydroxyphenyl)-;
Rikabanol; Ucar bisphenol A; Ucar bisphenol HP;
beta,beta0-Bis(p-hydroxyphenyl)propane; beta-Di-p-hydroxyphenylpropane;
p,p0-Bisphenol A; p,p0-Dihydroxy diphenyldimethylmethane; p,p0-Dihydroxydiphenylpro pane; p,p0-Isopropylidenebisphenol; and p,p0-Isopropyli denediphenol.
1.1.2 Formula and molecular mass. Bisphenol A
has a molecular mass of 228.29 g/mol and a molecular
formula of C15H1602 (European-Union, 2003). The structure
for bisphenol A is shown in Figure 1.
1.1.3 Chemical and physical properties. Bisphenol
A is a white solid with a mild phenolic odor
(European-Union, 2003). Physicochemical properties are
listed in Table 1.
1.1.4 Technical products and impurities. Purity
of bisphenol A was reported at 99–99.8%, and common
impurities observed were phenol and ortho and para
isomers of bisphenol A [reviewed in (European-Union,
2003)]. Terasaki et al. (2004) used reversed phase
chromatography and nuclear magnetic resonance spectroscopy
to characterize the composition of 5 commercial
bisphenol A samples. The nominal purity of the samples
was 97 or 98%. Actual purities were 95.3 to 499%. Up to
15 contaminants were identified among which were: 4hydroxyacetophenone;
4,40-(1,3-dimethylbutylidene) bisphenol;
p-cumylphenol; 4-hydroxyphenyl isobutyl
methyl ketone; 2,4
*
-dibhydroxy-2,2-diphenylpropane;
2,40-dibhydroxy-2,2-diphenylpropane; 2,4-bis(4-hydroxy-
HO
Fig. 1. Structure for bisphenol A.
CH 3
CH 3
OH
Table 1
Physicochemical Properties of Bisphenol A a
Property Value
Odor threshold No data found
Boiling point 2201C at 4 mm Hg; 3981C at 760 mm Hg
Melting point 150–1571C
Specific gravity 1.060–1.195 g/mL at 20–251C
Solubility in water 120–300 mg/L at 20–251C
Vapor pressure 8.7 x 10 -10 –3.96 x 10 -7 mm Hg at 20–251C
Stability/reactivity No data found
Log Kow 2.20–3.82
Henry constant 1.0 x 10 -10 atm m 3 /mol
a Staples et al. (1998).
Birth Defects Research (Part B) 83:157–395, 2008