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EC number: 202-500-6
CAS number: 96-33-3
Methyl acrylate is readily absorbed by the oral, dermal and inhalation
routes and the major portion is rapidly (1) hydrolyzed by
carboxyesterases to acrylic acid and methanol and/or (2) conjugated with
glutathione. In vivo, greater than 90 % is excreted within 72 hours,
primarily via the lungs (> 50 %) as CO2, and kidneys
(40-50 %) as products of methyl acrylate-glutathione conjugation. In
vitro tests using rat liver microsomes, Methyl Acrylate hydrolyzed to
form the metabolite acrylic acid (AA) with a half-life of less than 8.5
minutes. In whole rat blood in vitro, MA quickly metabolized, shown by
a significant and (nearly) complete loss of the parent acrylate. Based
on the measured concentrations of the remaning parent acrylate, the
half-life value for MA was less than 12 minutes in rat blood. MA formed
a single GSH conjugate in the presence of GST.
Dermal absorption is somewhat slower and appears to follow irritation of
the skin, possibly reflecting an initial de-esterification, with
subsequent absorption of the acrylic acid formed.
Discussion on bioaccumulation potential result:
Methyl acrylate is rapidly absorbed by the oral and inhalation routes
and distributed throughout the body. After oral or intraperitoneal
administration, greater than 90 % is excreted within 72 hours, primarily
via the lungs as carbon dioxide (> 50 %), and kidneys as products of
glutathione conjugation reactions (10-50 %) (Delbressine 1981, Sapota
1988 & 1990, Seutter 1981). The predominant pathway of metabolism of
methyl acrylate, by many tissues (including lung, liver, kidney and
plasma) appears to be hydrolysis to acrylic acid and methanol, which is
catalyzed by carboxyl esterase enzymes. Thus, under normal
circumstances, a relatively small amount of the intact ester is absorbed
into the blood through the lungs. The subsequent metabolism will follow
that for acrylic acid, and involves metabolism to carbon dioxide via the
propionate degradation pathway (acrylic acid --> 3-hydroxypropionic acid
--> malonyl semialdehyde --> acetyl S CoA --> --> tricarboxylic acid
cycle --> --> CO2). Metabolism of methanol proceeds via
a catalase peroxidative pathway or alcohol dehydrogenase pathway. Intact
methyl acrylate, which reaches the blood, is detoxified by hydrolysis,
as well as by conjugation (by Michael addition) with glutathione (GSH)
to form thioethers. The conjugates are then converted to mercapturic
acids and excreted in the urine. The main conjugate has been identified
as N-acetyl-S-(2-carboxyethyl)cysteine. Inhibition of the hydrolytic
pathway with carboxylase inhibitor results in increased metabolism via
the GSH conjugation route (Silver 1981, Miller 1981). There is no
evidence to suggest that the vinyl moiety undergoes epoxidation in vivo
Discussion on absorption rate:
Administration of 14C-methyl acrylate to the skin of guinea pigs under
occlusive conditions led to severe irritation, i.e. edema and necrosis,
confirmed histologically. The test compound penetrated slowly through
epidermis and dermis. A large part of the labeled acrylate was retained
in the dermis (Seutter and Rijntjes, 1981).
Autoradiography showed that metabolism of a locally administered dose
was practically limited to the skin in the first 24 h; subsequently,
labeled material was transported by the blood to the kidneys and
concentrated in the bladder, whereas other organs showed a slowly rising
concentration (Delbressine, 1979).
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