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Acetaldehyde as an industrial contaminant
Explores the usage of industrial chemical acetaldehyde scavengers
Date: 10/13/2012 2:50:16 PM ( 12 y ) ... viewed 20960 times One of the problems associated with using polyesters such as poly(ethylene terephthalate) (PET) for beverage containers is the generation of acetaldehyde during the melt processing of the polyester. Although the quantities involved are not a toxicity concern, over time such contamination can alter the flavor of the contents of the container. One technique for dealing with this problem is to incorporate acetaldehyde scavenging additives during production that react to form water and an organic byproduct that does not affect the taste of the beverage nor discolor the container. A suite of potential additives have been examined in this regard [1]. By design, additives were chosen that have sterically situated functional groups X and Y such as amine (NH2 and NHR), hydroxyl (OH), carboxyl (CO2H), amide (CONH2 and CONHR), sulfonamide (SO2NH2), or thiol (SH) that upon condensation with acetaldehyde form a stable 5- or 6-membered ring after the release of a water molecule.
For example:
Although these substances may be safe to use in an industrial application as described in the reference, many are orally toxic and not appropriate to even consider as ingested acetaldehyde scavengers. Then why document them here in a medical context?
The similarities and differences in molecular structures between these substances is a invaluable resource for comparison with known drugs and herbals that appear to be effective across a wide spectrum of diseases. If a commonality with a substance in this list is found that suggests that acetaldehyde binding may be occurring, then this may imply that yeast-released acetaldehyde is playing a role in the development of a disease of unknown origin.
Also, if a particular disease is characterized by the malfunction of a certain biochemical pathway in the body because of enzyme failure or diversion of critical substances away from necessary byproducts, then scrutiny of the structures of the biochemical participants in the pathway may reveal a structural commonality with a substance in this list that is known to form a complex with acetaldehyde. Again this would implicate acetaldehyde as a factor in the disease.
Some of the scavengers examined are biological substances (eg. arginine, asparagine, cysteine). The fact that they have been shown here to form complexes with acetaldehyde indicates that commensal yeast may already be interfering with their supply and absorption resulting in deficiency conditions relating to their particular functions in the body.
And finally, there is always the possibility that a scavenger that has been tested in an industrial setting may be biologically compatible, suitable, and ideal for therapeutic usage.
Information on the biological activities of small molecules has been centralized by the National Center for Biotechnology Information into a massive database PubChem with data on 100 million substances and 200 million bioactivites [2]. Of particular interest to this study for any given substance are the additional links in PubChem to "Biomedical Effects and Toxicity" and "Literature". Information in this section may also contain links to the National Cancer Institute's Yeast Anticancer Drug Screen [3] where tens of thousands of compounds have been methodically screened for their potential to inhibit the growth of yeast strains altered in DNA damage repair or cell cycle control [4].
As important as finding molecular configurations with anti-cancer properties may be in the treatment of malignancies, if cancer as a disease is a disruption in metabolic cellular regulation, repair, and destruction processes, then the administration of anti-cancer drugs alone will not correct the imbalance in the body that allowed the cancer to initiate and persist or to reappear. There is no doubt that acetaldehyde is a carcinogenic substance. Chronic exposure to this toxin emanating from commensal Candida fermentation of dietary carbohydrates may set the stage for downstream carcinogenic processes. This being true, then just as much effort needs to be expended in finding ways of dealing with the upstream cause of cancer as well as the downstream consequences.
The compounds tested in the industrial search for an acetaldehyde scavenger in the processing of melted polyester are itemized herein with notes and links to the PubChem database. They are listed in decreasing order of efficacy (i.e. ring-forming reactivity with acetaldehyde) for the specific tests performed. The relative performance is indicated by the number of asterisks in the note from 0 to 4. From the diversity of structural arrangements that show ring closure reactivity with acetaldehyde, it should be glaringly obvious why this substance is so dangerous in the body. It can react with and incapacitate just about any biological configuration it encounters.
CAUTION: This information is for reference only. Unless specifically stated to the contrary, all of these substances should be considered to be potentially toxic and not appropriate for therapeutic management of yeast-released acetaldehyde.
The configurations with profiles that have the most potential for more testing in their possible physiological roles as acetaldehyde scavengers are methyl anthranilate (cf. grape diet cure) and 3-mercapto-1,2-propanediol (monothioglycerol).
[1] Rule et al., "Method To Decrease The Acetaldehyde Content Of Melt-Processed Polyesters", US Patent 6274212, 2001.
http://www.google.com/patents/US6274212?printsec=abstract#v=onepage&q&f=false
[2] National Center for Biotechnology Information, "PubChem Bio Assay / Compound / Substance Database", 2004.
http://pubchem.ncbi.nlm.nih.gov
[3] National Cancer Institute, "NCI Yeast Anticancer Drug Screen Database", 2002.
http://dtp.nci.nih.gov/yacds
[4] Hobeck S et al., "The FHCRC/NCI Yeast Anticancer Drug Screen" in "Yeast as a Tool in Cancer Research", 2007, 315-346, DOI: 10.1007/978-1-4020-5963-6_12
http://www.springerlink.com/content/jg57235741j2471k
List of Acetaldehyde Scavengers Tested
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Notes: ring closure condensation reaction with acetaldehyde (****).
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=68067&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (****).
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=69263&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (***).
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6942&loc=ec_rc
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Notes: ring closure condensation reaction with acetaldehyde (***). Allantoin is present in botanical extracts of the comfrey plant and urine from cows and most mammals. It is used topically in many cosmetics and skin care products. Because uric acid may be oxidized to allantoin by various reactive oxygen species, it is postulated that uric acid functions as an antioxidant in human bodily fluids [5].
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=204&loc=ec_rcs
[5] Lagendijk et al., "The Determination of Allantoin, a Possible Indicator of Oxidant Status, in Human Plasma", J Chromatogr Sci (1995) 33 (4): 186-193.
http://chromsci.oxfordjournals.org/content/33/4/186.abstract
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Notes: ring closure condensation reaction with acetaldehyde (***). Derivatives of salicylanilide have a variety of pharmacological uses with antibacterial and antifungal activities.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6872&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (***). Salicylamide is a non-prescription drug with analgesic and antipyretic properties used in a manner similar to aspirin.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5147&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (***). Side to side carbonyls in an ester configuration are present in dimethyl fumarate which is being investigated in relation to relapse-remitting multiple sclerosis.
• See "Acetaldehyde + Dimethyl Fumarate" http://curezone.org/blogs/fm.asp?i=1989754
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7911
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Notes: ring closure condensation reaction with acetaldehyde (**). Monothioglycerol is classified as an antioxidant, an antimicrobial, a cosmetic agent, a stimulator of wound healing, and as a jelly in atrophic rhinitis [6].
[6] Rowe et al., "Monothioglcerol" in "Handbook of Pharmaceutical Excipients", Sixth Edition, Pharmaceutical Press, 2009.
The effectiveness of monothiogycerol in rhinitis may result from its ability to quench yeast-released acetaldehyde before it initiates a cascade of peroxidation:
• See "Acetaldehyde + Pulmonary Peroxidosis" http://curezone.com/forums/fm.asp?i=1984937
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7291&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (**).
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9956&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (**).
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=15652&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (**). Biuret is the result of condensation of two molecules of urea. It is used as a non-protein nitrogen source in ruminant feed. The "Biuret Test" is a chemical test used for detecting the presence of peptide bonds, for diagnosis of hyperproteinuria for example. Biuret reagent is so-named, not because it contains biuret, but because of its reaction to the peptide-like bonds in the biuret molecule.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7913&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (**).
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1531&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (**). Also known as disodium chromotropate. The chromotropic acid method can be used to determine the concentration of formaldehyde in ambient air samples.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=67220&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (**). This is a derivative of para-aminobenzoic acid (PABA) which is an intermediate in the bacterial synthesis of folate.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=137566&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (*). This has a medical use as a carrier ligand in oxaliplatin, a platinum-based antineoplastic agent used in cancer chemotherapy.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4610&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde (*). This is a derivative of the amino acid glycine.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=75800&loc=ec_rcs
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The following substances were found to be capable of forming 5- or 6-member rings upon condensation with acetaldehyde but were thermally unstable under the conditions of the industrial process in question (heating with polyester at 150 C for 45 min). This is far beyond the most extreme of physiological conditions and these substances should not be ruled out based only upon their thermal instability in this particular application.
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Notes: ring closure condensation reaction with acetaldehyde. Arginine is a conditionally non-essential amino acid that participates in protein biosynthesis in the body.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6322&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde. Asparagine is a non-essential amino acid that participates in protein biosynthesis in the body.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6267&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde. Aspartic acid is a non-essential amino acid that participates in protein biosynthesis in the body.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5960&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde. Cysteine is a non-essential amino acid that participates in protein biosynthesis in the body. It can be biosynthesized from serine and methionine. An acetaldehyde-scavenging formulation called Acetium® is currently being marketed in Finland and Germany.
• See "Acetaldehye + Cysteine" http://curezone.com/forums/fm.asp?i=1973900
• See "Acetaldehyde + Sulfur Metabolism" http://curezone.com/forums/fm.asp?i=1977201
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5862&loc=ec_rcs
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Notes: ring closure condensation reaction with acetaldehyde. Serine is a non-essential amino acid that participates in protein biosynthesis in the body.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5951&loc=ec_rcs
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The following substances were tested as additives but found to be incapable of forming 5- or 6-member rings upon condensation with acetaldehyde. They are included here for comparison with the structures that do form rings.
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Notes: no ring closure condensation reaction with acetaldehyde. No PubChem database entry.
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Notes: no ring closure condensation reaction with acetaldehyde.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=79336
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Notes: no ring closure condensation reaction with acetaldehyde. Glycine is a non-essential amino acid that participates in protein biosynthesis in the body. It is also a neurotransmitter.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=750&loc=ec_rcs
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Notes: no ring closure condensation reaction with acetaldehyde. Although there was no ring closure byproduct in this application, methyl anthranilate is used in the perfume industry to form Schiff bases with aldehydes. Since methyl anthranilate occurs naturally in Concord grapes, its formation of a Schiff base with acetaldehyde may provide the basis for Johanna Brandt's "grape diet" cure by functioning as an acetaldehyde scavenger. The steric proximity of the electron-rich ester may favor and stabilize the formation of the resulting configuration.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8635&loc=ec_rcs
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Notes: no ring closure condensation reaction with acetaldehyde.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=31292&loc=ec_rcs
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Notes: no ring closure condensation reaction with acetaldehyde. Piperazine is used as an anthelmintic for paralyzing parasites.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4837&loc=ec_rcs
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Notes: no ring closure condensation reaction with acetaldehyde. Stearylamine in liposomes is being investigated for inhibition of the growth of the protozoan parasites.
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=15793&loc=ec_rcs
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