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Aspartame

Aspartame(Aspartame, Aspartame, abbreviation APM ; pronunciation [ˈæsphusbandtm] or [əˈspɑːrtm]) IsArtificial sweetenerIs one of.For humanssucrose100-200 timessweet tasteIt feels like.On the other hand, aspartamePhysiological calorieIs about 4 (kcal / g), which is almost the same as sucrose, and is not non-calorie.CAS Registry NumberIs [22839-47-0].

Structure / properties

AspartameL-PhenylalaninemethanolAndDehydration condensation and esterOf the phenylalanine methyl ester that formedAmino groupWhen,L-aspartic acid OfCarboxylic acid groupAndDehydration condensation and peptide bondIt has a structure that forms.

taste

Aspartame for humanssucrose100-200 timessweet tasteFeel[2]..Its taste is described as "sweet afterwards, with a slight backlash, and is close to sugar and soft."

For reference, what feels sweet is that both phenylalanine and aspartic acid must be in the L form, otherwise they feel bitter.

Physicochemical properties

Aspartame at normal pressureDecomposition pointIs between 246 ° C and 247 ° C.At normal temperature and pressure, aspartame exists as a white crystalline powder.Aspartame has peptide bonds and even ester bonds in its structure, so it is somewhat unstable to acids and bases, especially when the temperature rises.[Annotation 1]..For this reason, it is evaluated that the long-term stability in the presence of water is inferior to that of other food additives.The solubility of aspartame is about 20 (g / L) in water at 10 ° C.

Dynamics

AspartameHuman capital,monkeyWhen orally administered to, it is broken down in the digestive tract andmethanol,L-aspartic acid,L-PhenylalanineFree.These are easily absorbed from the intestinal tract and enter the body. L-aspartic acid and L-phenylalanine are naturalamino acidIs.Therefore, it has been reported that after being absorbed, it is metabolized in the same way as normal amino acids, used as a protein material in the body, deaminated, and then decomposed as an energy source.[3][4]..Because of this, aspartamePhysiological calorieIs said to be about 4 (kcal / g), which is similar to general proteins.[Annotation 2].

Methanol, on the other hand, is oxidized after being absorbed.Formaldehyde, Further oxidizedformic acidCausesblindnessIt is known to be toxic to the human body, such as lethal.However, the amount of aspartame normally used as a seasoning is very small.[5]For healthy people, acute toxicity due to liberated methanol etc. is virtually not a problem.[6][7]..For more information on toxicity, see "Risk and safety assessmentSee section.

Use

Aspartame in the structureEster bondlikeHydrolysisAlthough it is inferior in long-term stability in a moist state because it has a part that is susceptible to it, it is suitable for low-calorie beverages and foods worldwide.Food additiveIt is used as.Moreover, not aspartame alone,sugar,Acesulfame potassium,SorbitolMay be used in combination with other sweeteners[Annotation 3].

Also, in Japan, it is legally permitted to label beverages of 100 kcal or less per 5 mL as "non-calorie", so aspartame is added to "non-calorie beverages" even though it is not non-calorie. There may be.

History

1965 ToThe United States of America OfSearle chemicalsBut,GastrinThe research and development was advanced with the discovery of a strong sweetness during the synthetic research of.The aspartame developed in this way is available in Japan and the United States.1983 Was approved for use as a food additive.In Japan,Ministry of Health and WelfareDoes not exist naturallyAdditiveClassified into[8], Foods and additives that use aspartame are obliged to "label that they are L-phenylalanine compounds or that they contain them".

Japan Consumers' Cooperative FederationHas not handled foods containing aspartame due to safety concerns, but in March 2002, it decided to exclude it from the additives used with caution, and lifted the handling restrictions.The current manufacturing method was developedAjinomoto Co., Inc.And Japan, United States, Canada, andEuropean UnionPatenthave[9].

Safety assessment

Aspartame is a non-naturally occurring compound[8]..Aspartame is broken down in the digestive tract and is toxic in addition to amino acidsmethanolHas been found to be liberated.However,United States Food and Drug Administration According to the (FDA) review, the amount normally used as a seasoning is very small, so if you are a healthy person, you will not have any problems with acute toxicity or chronic toxicity.[6][7]..In addition, the FDA says aspartame does not cause allergies in healthy people.[10].

For the pharmacokinetics of aspartame,Human capital,monkey OfSmall intestineAtmethanol-Aspartic acid,andPhenylalanineMetabolized and absorbed in the bodyproteinIs annexed tocarbon dioxideHas been reported to be excreted as[11][12]..Of these, methanol isblindnessAlthough it is known to be toxic to the human body such as lethal and lethal, it is also contained in fruits, vegetables and alcohol, and it is negligible in a trace amount. CitrusjuiceIt is known that it is less than the amount taken from and is not a problem.[6][5].

Regarding phenylalanine, it is a congenital genetic abnormality.PhenylketonuriaThe FDA points out that in patients, phenylalanine cannot be metabolized well in the body, which may exacerbate symptoms.[10]..Therefore, it is desirable that patients with phenylketonuria do not consume foods containing aspartame.

For aspartameBrain tumorAlthough there was a report pointing out the relationship with, it was denied in the retest[13]..In addition, aspartame has not been found to be carcinogenic in tests that comply with the scientifically confirmed carcinogenicity test guidelines.[14]..Because of this,International Cancer Research Institute(IARC) also has aspartameCarcinogenicIt is not classified as a substance with.

Meanwhile, according to a 2007 CBS NEWS report, it was commissioned by the Ramazzini Foundation.Mount Sinai Medical CollegeDr. Morando Soffritti,RatFrom the fetal stage to death, the incidence of cancer was as a result of continuing to administer aspartame twice the daily allowable daily consumption (about 1 g; 2 cans / day with diet soda) set by the FDA. Research results show that there is a statistical increase in[15].

However, the European Food Safety Authority (EFSA) has reviewed this report andDose-responsiveIt was concluded that the data was inappropriate and insufficient as a basis for reconsideration, citing the absence of data and the fact that there was no difference in mortality from the control group. "Our conclusions (aspartame approval) are based on more than XNUMX toxicity and clinical trials," the FDA said of the Ramazzini Foundation's results.[16]..A 7,000 case-control study of more than 2007 people in Italy found that artificial sweeteners containing aspartame were not carcinogenic.[17]..Sofrito et al. Do not mention these results, which differ from their own views.[18].

Derivative

United StatesMonsantoIs the reducing N- of aspartameAlkylationAs a dipeptide methyl ester derivative synthesized byNeotame(en: Neotame) Was developed.Neotame is said to be about 1 times as sweet as sucrose.

Ajinomoto Co., Inc. is a derivative of aspartame.AdvantameDeveloped[19]..This is what aspartame hasAmino groupIt is a chemically modified compound and is said to have 2 times the sweetness of sucrose.[20].

Advantame is2014 ToUS Food and Drug AdministrationEuropean CommissionFromFood additiveApproved as[21], In Japan in 2014Ministry of Health, Labor and WelfareApproved by[22], Started to be sold as a food additive.

Neotame and Advantame each generate 1 methanol per molecule during metabolism, similar to aspartame.

footnote

[How to use footnotes]

注 釈

  1. ^ For example, stomach acid helps break down proteins, which helps hydrolyze peptide bonds in proteins.In addition, ester bonds are more easily hydrolyzed by acids and bases, oftenTransesterification reactionAnd so on.In general, a chemical reaction is more likely to occur at a higher temperature.
  2. ^ So-calledAtwater coefficientIs.The amount of metabolizable sugars such as sucrose is also about 4 (kcal / g).
  3. ^ For example, a 1: 1 combination of aspartame and acesulfame potassium enhances sweetness by 40%, and sweetness adjustments are often performed by using sweeteners, as it is said that the rise of sweetness is closer to that of sugar. Be struck.

Source

  1. ^ Merck Index, 11th Edition, 861.
  2. ^ "How to use sugar substitutes""E-Health Net" Ministry of Health, Labor and Welfare, Retrieved October 2010, 10. (Archive version)
  3. ^ Opperman JA et al; J NUTR 103 (10): 1460-6 (1973)
  4. ^ Trefz F et al; Human Genetics 93 (4): 369-74 (1994)
  5. ^ a b Butchko, H; Stargel, WW; Comer, CP; Mayhew, DA; Benninger, C; Blackburn, GL; De Sonneville, LM; Geha, RS et al. (2002). “Aspartame: Review of Safety”. Regulatory Toxicology and Pharmacology 35 (2 Pt 2): S1–93. two:10.1006 / rtph.2002.1542. PMID 12180494. 
  6. ^ a b c Henkel, John (1999). “Sugar Substitutes: Americans Opt for Sweetness and Lite”. FDA Consumer Magazine 33 (6): 12–6. PMID 10628311. オ リ ジ ナ ルArchived as of October 2007, 1.. https://web.archive.org/web/20070102024642/http://www.fda.gov/fdac/features/1999/699_sugar.html. 
  7. ^ a b Magnuson, BA; Burdock, GA; Doull, J .; Kroes, RM; Marsh, GM; Pariza, MW; Spencer, PS; Waddell, WJ et al. (2007). “Aspartame: A Safety Evaluation Based on Current Use Levels” , Regulations, and Toxicological and Epidemiological Studies ”. Critical Reviews in Toxicology 37 (8): 629–727. two:10.1080/10408440701516184. PMID 17828671. 
  8. ^ a b Ministry of Health and Welfare "Table 5 Intake of Food Additives by Age"Survey of daily intake of food additives by age group by market basket method (December 2000, 12, Ministry of Health and Welfare) (Japan Food Chemistry Research Promotion Foundation)
  9. ^ Sweets, invention consideration 1 million yen Ajinomoto patent proceedings decision - Kyoto Shimbun, February 2004, 2. (As of March 24, 2005Archive
  10. ^ a b FOOD ALLERGIES RARE BUT RISKY(As of January 1999, 1Archive
  11. ^ Opperman JA et al; J NUTR 103 (10): 1460-6 (1973)
  12. ^ Trefz F et al; Human Genetics 93 (4): 369-74 (1994)
  13. ^ FDA Statement on Aspartame, November 18, 1996. (As of May 1997, 5)Archive); — The FDA's statement on aspartame and tumors included PBOI's report pointing to a link to brain tumors in the 70s.RatHe explained that he approved it based on the fact that it was not reproduced in the retest in Japan and that it was not reproduced in the additional test in Japan.It also explains that there have been no significant changes in brain tumor epidemiological studies in the United States since the launch of aspartame.
  14. ^ BRYAN, GT; ARTIFICIAL SWEETENERS AND BLADDER CANCER: ASSESSMENT OF POTENTIAL URINARY BLADDER CARCINOGENICITY OF ASPARTAME AND IS DIKETOPIPERAZINE DERIVATIVE IN MICE;
  15. ^ Aspartame's Safety Questioned Again
  16. ^ Artificial Sweeteners: No Calories ... Sweet!(As of January 2006, 8Archive
  17. ^ S Gallus, Artificial sweeteners and cancer risk in a network of case–control studies; Annals of Oncology 2007 18 (1): 40-44; doi: 10.1093 / annonc / mdl346
  18. ^ Environ Health Perspect. Doi: 10.1289 / ehp.10881
  19. ^ “FDA Approves New No-Calorie Sweetener”. Medscape(July 2014, 5). http://www.medscape.com/viewarticle/825427 October 2014th, 5Browse. 
  20. ^ "Food Additives & Ingredients --Additional Information about High-Intensity Sweeteners Permitted for Use in Food in the United States". October 2018th, 1Browse.
  21. ^ Ajinomoto Co., Inc.'s new sweetener "Advantame" obtained food additive approval in Europe and the United States, May 2014, 5, Ajinomoto, October 27, 2017
  22. ^ Ajinomoto / new sweetener "Advantame" approved in Japan, January 2014, 6, read January 18, 2017

References

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