User:Douglian30/sandbox/talk drafts

Rev. Hodgson and the foundation of WBA
The article on Robert Hodgson (diplomat) states that his father, the Reverend Robert Hodgson, was "founder of West Bromwich Albion Football Club", without citation. The history on the WBA website and in Gavin McOwan's book describe the roots in Salter's and the name change from Strollers to Albion, but do not name specific founders (just the first reported players). Father and son were associated with the town of West Bromwich in the 1870s, but was there any link to WBA FC? If there is no reliable, sourced information that there was, I will delete the phrase in the Hodgson article.

Opening lead paragraph (May 2023)
The statement "Cholesterol is any of a class of certain organic molecules called lipids." is wrong. Cholesterol is not "any of a class", it is a single, (stereo)specific chemical compound. It is a member of the sterols, which (as stated and explained in the Sterol article) are a class of steroid, having a 3-hydroxy group, not a modified steroid. The scope note for the MeSH term Cholesterol reads "The principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils". This could be the basis for a revised opening to the lead section, namely: "'Cholesterol is the principal sterol (a steroid with a hydoxy group in position 3) of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils."

Also, the sentence "When chemically isolated, it is a yellowish crystalline solid." is at odds with the entry "Appearance = white crystalline powder" under Properties. Yellow coloration may have resulted from imperfect purification in earlier isolations and the inclusion of the sentence in the lead section is probably unnecessary anyway.

The present text of the lead section needs to be corrected ASAP. Unless there are any adverse comments or suggested improvements, I'll edit the text.

Litvinov – Seeds
The belittling of the French ambassador was accidental. On 29 March, I clarified and added links for the CE's [who?] flags, including Seeds, but neither of us paid attention to unnamed persons. There are some further links that I have now added (Ilya Ehrenburg, Andrey Andreyevich Andreyev, Georgi Dimitrov) and also Gen. Lesley J. McNair (after inserting a comma to indicate that he hadn't been elevated to VP!).

Disagreement in numbers
The "Clinical Significance" section, the last paragraph, seems to have some weird numbers in it. One example: "These groups were more likely to die of cancer, liver diseases, and mental diseases with very low total cholesterol, of 186 mg/dL (10.3 mmol/L) and lower." -- 10.3 is not very low, it's very high. Someone should run a check there. --CopperKettle (talk) 05:54, 18 July 2023 (UTC)

Tautomers and nomenclature
Some of the chemical information in the article is questionable, including the (unreferenced, but ranked) list of named tautomers and some of the structures and names in the linked external datasets listed in the Chemical Infobox. Also, the article does not cover recent publications. An update of the Chemistry section might include: There are eight possible structures for creatinine, including geometric isomerism of the 2-imino tautomers, although enolic forms are significantly less stable than their ketonic counterparts and can be discounted. Only the amine tautomer of creatinine has been experimentally characterized in polar solvents or the solid state, while both imine and amine tautomers have been observed in gasphase spectroscopic studies.

The general statement that creatinine tautomers are in equilibrium is not really accurate under normal conditions. In aqueous environments, both hydrogen bonding with the inner solvation-shell of water molecules and overall polar-solvent effects stabilise the amino form, with pH also having a significant effect [with high pH increasing ring cleavage to (re)form creatine]. Thus amine-imine tautomerism may not be relevant in a biological context (other than in possible mechanistic routes) and keto-enol tautomerism probably can be disregarded.

The Wikipedia article on Tautomers covers implications for databases, noting the advantages of notation, but this leaves the problem of nomenclature if Creatinine is to be named systematically, since such names are specific to a single structure. Fortunately, on the basis of the above (but not the existing article), it seems reasonable to base the preferred name on the amine structure. Unfortunately, the quality of structural and naming information for Creatinine in the Chemical Infobox and some of the external databases listed is variable, to put it politely and in the light of the text proposed above. To enumerate the points:


 * 1) IUPAC Preferred Name: Naming of the parent cycle of the 2-amino-4-one and 2-imino-4-one tautomers differs because in the former the ring contains unsaturation, whereas in the latter it is saturated (but with conjugation through the 3-N lone pair), resulting in the stems "diazole" and "diazolidine", respectively, under  Hantzsch–Widman rules. In the 2-amino structure, the partial ring saturation is reflected by indicated hydrogen (xH) and "dihydro" terms, with appropriate locants.
 * 2) Whether "Other names" should just include variants for the 2-amino structure or also for the 2-imino structure is a moot point.
 * 3) CHEBI:16737 and CHEMBL65567 (Creatinine) give the structure and names of the 2-imino form, as does DrugBank DB11846 and KEGG D03600.
 * 4) ChemSpider 21640982 (Creatinine) gives the structure and names of the 2-amino-4-hydroxy compound with a doubly unsaturated diazolidine ring.
 * 5) ECHA InfoCard	100.000.424 and EC number: 200-466-7 use 2-imino-1-methylimidazolidin-4-one as the heading for Creatinine.
 * 6) MeSH term Creatinine (D003404) - sanity at last!
 * 7) PubChem CID 26009888 is 2-amino-1-methyl-1H-imidazol-4-ol, an isomer of Creatinine, but according to the reference cited above not a significant tautomer.  The PubChem CID for Creatinine is 588; it supplies the 2-amino-4-one structure, but includes the 2-imino form amongst the list of synonyms.  It was the illogically of calling Creatinine a minor tautomer of Creatinine that originally suggested that there might be problems in the information for the compound.
 * 8) UNII: AYI8EX34EU uses the 2-amino structure, but supplies some 2-imino names.  The linked Inxight Drugs database has the 2-amino structure but gives 2-Imino-1-methylimidazolidin-4-one as the "Systematic Name", relegating 2-amino names to "Common Name"s!
 * 9) CompTox Dashboard (EPA) DTXSID8045987 shows the 2-imino structure and provides "IUPAC Name: 2-Imino-1-methylimidazolidin-4-one".

This seems an unsatisfactory situation for the information on a biologically significant compound, with it being unclear why databases prefer a structure that is not normally observed in reality. Is this really the case and what should be done about it?

Polyunsaturated fats redirection
The redirection from Polyunsaturated fats to Polyunsaturated fatty acids is inappropriate, because these are distinctly different, if related, concepts. Polyunsaturated fatty acids, together with the corresponding Saturated fatty acids and Mono-unsaturated fatty acids terms are 3 mutually exclusive classes of chemical compound. On the other hand, Polyunsaturated fats and the corresponding terms for saturates and mono-unsaturates are nutritional constructs used to quantify the amounts of each type of fat in a food based on their fatty acid profiles. This is well illustrated in the article on Triglycerides, where the structural diagram of a mixed triglyceride shows a molecule that is one-third saturated fat, one-third mono-unsaturated fat and one-third polyunsaturated fat (the caption text "an unsaturated fat triglyceride" should be read as "an unsaturated fat-triglyceride", not "an unsaturated-fat triglyceride").

The fat and corresponding fatty acid terms are NOT synonymous. The fatty acid terms name specific categories of chemical compound, whereas the fat terms represent derived concepts, with compositional values calculated. The logical difference is well illustrated in the article on Triglyceride, where the structure of a "mixed triglyceride" shows a molecule that contributes (nearly) one-third each of saturated, mono-unsaturated and polyunsaturated fat. The "nearly" arises because the calculation excludes the weight contributed by the glycerol backbone. This is explained in more detail in Danish Food Informatics's description of Fatty acids in foods. Thus the relationship between the fat and corresponding fatty acid terms are See also ones, not See redirections. To avoid needless repetition, the description of the fat terms might be generalised in the Fat section or in a new, linked article on Types of fat.

BNF revision
The current version of the BNF article has broken links, incomplete references and is not particularly informative. Rather than make separate comments or individual edits, it is perhaps simpler to do a full redraft, as follows:



The British Nutrition Foundation is a British registered charity and company limited by guarantee that works to share scientific knowledge and advice on diet, physical activity and health.

Activities
The BNF aims to give the general public, educators and organisations access to reliable information on nutrition. Its website provides details on healthy, sustainable diets, on nutrition at different life stages, on diet in relation to health issues and on putting advice on diet and nutrition into practice. Training is provided through online courses and webinars, with past webinars available on the website, together with videos of previous annual conferences. The organisation runs an annual “Healthy Eating Week” each June.

The BNF manages the educational programme Food – a fact of life (FFL). This is designed to support teachers by providing accessible information on diet and health for children and young people progressively through the ages 3 years to 16+ years. It was originally launched in 1991 in a partnership with MAFF that continued until 1997. The BNF continued to develop the educational resources and from 2018 the FFL programme has been a partnership between the BNF and the Agriculture and Horticulture Development Board.

The official journal of the BNF, Nutrition Bulletin, is an international, peer-reviewed journal published quarterly by Wiley. Its coverage has included review articles and news items on nutrition, but since acquisition of an impact factor and MEDLINE coverage an increasing number of papers reporting original research have been included; many articles are open-access.

Governance
Under its Memorandum and Articles of Association, the Board may comprise no more than 12 Trustees. Trustees are appointed by the Board and serve for a term of three years, with each Trustee able to serve for a maximum of nine years; membership of the Board is weighted towards the scientific academic community. As a charity largely funded by corporate donations from food industry organisations, the BNF maintains its independence through advisory and scientific committees, an Editorial Advisory Board, educational working groups and a register of interests for Board members and senior managers.

Finances
In 2021-22, the charity had an income of £1.35million, with an expenditure of £1.33million.

Criticism of food industry links
A 1985 World in Action documentary interviewed Derek Shrimpton, a previous director general at BNF, who said: "In the period I was there the foundation was solely taken up with defence actions for the industry." He also said that BNF worked to frustrate government committees working on policies to reduce sugar, salt, and fat consumption.

In 2005, 26 UK MPs signed an Early Day Motion in Parliament concerning the BNF advising the government on food nutrition while receiving funds from the food industry.

Further concerns about the BNF's relationship with the food industry were raised in a 2010 British Medical Journal article, also published in a shortened form in The Independent, which criticized the way in which the BNF was treated as a source of impartial nutritional information by the media, usually without describing the industry ties, with funding members including, for example, Cadbury, Kellogg and McDonalds. It also criticized the UK government for paying the BNF to develop educational materials on nutrition, and quoted Tim Lobstein, a director at the International Association for the Study of Obesity-International Obesity Task Force (now the World Obesity Federation), saying that some BNF educational materials seem to support industry messages.

Definitions for types of fat
Now that it seems decided, if not implemented, that information covering each type of Fat and the corresponding set of Fatty acids should form a single, combined article, named according to the Fat rather than the Fatty acids, it needs to be decided what editing of the articles is needed to describe the types of fat adequately. The starting point should be to describe the article subject correctly. For example, in MUF, the statement "Monounsaturated fats are triglycerides containing one unsaturated fatty acid." is wrong. Triglycerides with 1, 2 or 3 MUFAs all contribute to MUF, only in differing amounts. The articles on SF (Saturated fat), MUF and PUF make no mention at all of the legal definitions of the terms, as mandated for the nutritional labelling of foods, although these are precise. These have minor variations, for example between the US and Europe, but these definitions should be clear as they determine the information most seen by consumers. These defined terms also include Total fat (TF). FT redirects to Fat, an article that emphasises that Fat can have varying meanings. FT is mentioned several times in the article, but is undefined.

Apart from definitions, much further editing is needed in the articles relating to fats. For example, in PFA#Reactions, how many edits are required in the paragraph "Hydrogenation of PUFAs gives less saturated derivatives. For unsaturated products from partial hydrogenation often contain some trans isomers. The trans monounsaturated C20 species elaidic acid can be prepared in this way."? The articles in this area are important and do need further attention.

Analysis and quantification draft


Analysis and quantification
Polyunsaturated fat is not a discrete, uncombined substance and therefore cannot be directly analysed. Instead, in food analysis, the lipids are isolated by solvent extraction, followed by alkaline hydrolysis of the solute. The resultant free fatty acids are re-esterified, for example to methyl esters or, when short-chain fatty acids are significant, to butyl esters. The mixture of fatty acid esters is then analysed by gas chromatography, with each fatty acid identified by its retention time and quantified by the area under each peak.

The total for polyunsaturated fat is obtained by summating the amounts determined for the relevant individual fatty acids, namely PUFAs with two or more cis, cis-methylene interrupted double bonds, as defined in the EU regulation on food labelling. The total is expressed as the weight of the PUFAs, as it is in the British FCD, but in the US the  NLEA requires the amount to be expressed as triglyceride equivalents.

Fat types 2
Yes, a good step forward, but a little more is needed; it does not take account of the point that I made above about how 1, 2 or 3 MUFAs in a triglyceride contribute to the MUF total. Consider a hypothetical "pure" triglyceride in which only the same set of 3 fatty acids occur in the triglyceride molecules. If one of the three fatty acids is a MUFA, then 100g of the triglyceride will contribute 33g to the MUF total. However, if two of the three are MUFAs, then the contribution is 67g and if all three are MUFAs, the contribution is 100g. None of the existing articles on the types of fat make this clear, although it is key to any quantitative work using food composition data and to meeting food labelling regulations. I intend to draft an extra section, initially for the PUFA/PUF article, on "Analysis and quantification", which I will post for discussion. Hopefully a clear and concise description of the analysis of fatty acids in foods and the construction of the fatty acid/fat totals from these analytical results will improve the understandability (and accuracy) of the articles.

Definition of MUF
The existing definition of MUF is somewhat inaccurate and misleading. An improved text for the lead section might read:

In biochemistry, nutrition and food composition data, monounsaturated fat (MUF) is fat consisting of monounsaturated fatty acids (MUFAs), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being single-bonded. By contrast, polyunsaturated fatty acids (PUFAs) have more than one double bond.

Most MUF in foods or other materials is present as MUFA esters, chiefly as triglycerides. The total of MUF is determined by extracting all the fatty acids, identifying and quantifying the individual fatty acids, and then summating the results for all individual MUFAs.

On the basis of this definition, the opening sentence of the Molecular description section is incorrect, as is the caption of the molecular structure diagram. Certainly this shows a monounsaturated triglyceride, but it is not a MUF. It contains two saturated fatty acids and one MUFA. Thus it contributes two parts saturated fat and one part MUF.

Also, the statement "Almost invariably that fatty acid is oleic acid (18:1 n−9)" may apply in some cases, but is wide of the mark for many foods. For example, using data from the UK tables, 100g of raw herring contains 1.06g 16:1, 1.50g 18:1, 1.26g 20:1 and 2.01g 22:1. Further, highlighting the values for MUF in red and green (why the difference?) in the table risks carrying an implication that is not intended.