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1. Sweet surfactants I: Fatty acid esters of sucralose

Author:
Łukasz Tabisz; Zuzanna Piotrowicz; Marta Dąbrowska; Anna Dobrowolska; Katarzyna Czaczyk; Izabela Nowak; Bogusława Łęska
Source:
Food chemistry 2021 v.358 pp. 129827
ISSN:
0308-8146
Subject:
detergents; fatty acids; food chemistry; hydrophilicity; hydrophobicity; sucralose; sucrose; sweetness
Abstract:
... Surface active agents derived from the non-toxic sweetener sucralose and fatty acids of different chain length were synthesized. Obtained compounds were characterized chemically and with regard to their properties as emulsifying agents, antimicrobial preservatives and fat-soluble sweeteners. Results show that sucralose-fatty acid esters are possible multi-purpose additives, compatible with both ...
DOI:
10.1016/j.foodchem.2021.129827

2. Microbial inhibitory properties of maltodextrin fatty acid esters against food-related microorganisms

Author:
Namhyeon Park; Marie K. Walsh
Source:
Lebensmittel-Wissenschaft + [i.e. und] Technologie 2021 v.147 pp. 111664
ISSN:
0023-6438
Subject:
esterification; fatty acids; food quality; glucose; hydrophilicity; maltodextrins; solubility; sucrose
Abstract:
... Carbohydrate fatty acid esters (CFAs) are increasingly used to improve food quality and safety but may have limited applications due to their low aqueous solubility. The use of hydrophilic maltodextrin for the synthesis of CFAs results in compounds with high aqueous solubility, but knowledge of their microbial inhibitory properties is lacking. The aim of this study was to evaluate the microbial ...
DOI:
10.1016/j.lwt.2021.111664

3. Potential physio-pathological effects of branched fatty acid esters of hydroxy fatty acids

Author:
Melha Benlebna; Laurence Balas; Sylvie Gaillet; Thierry Durand; Charles Coudray; François Casas; Christine Feillet-Coudray
Source:
Biochimie 2021 v.182 pp. 13-22
ISSN:
0300-9084
Subject:
animals; biosynthesis; fatty liver; glucose tolerance; human health; insulin resistance; insulin secretion; synthesis; therapeutics
Abstract:
... Branched Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) are a new endogenous lipid class with recently uncovered interesting biological effects and which have been detected in food of plant and animal origins. Some FAHFAs can improve glucose tolerance and insulin sensitivity, stimulate insulin secretion, and exert anti-inflammatory effects. Other beneficial health effects have also been ...
DOI:
10.1016/j.biochi.2020.12.020

4. Effect of cellulose and starch fatty acid esters addition on microstructure and physical properties of arabinoxylan films

Author:
Swati Kanwar; Usman Ali; Koushik Mazumder
Source:
Carbohydrate polymers 2021 v.270 pp. 118317
ISSN:
0144-8617
Subject:
arabinoxylan; cellulose; crystal structure; esterification; microstructure; palmitates; permeability; potato peels; starch; stearic acid; strength (mechanics); water vapor; wheat straw
Abstract:
... Arabinoxylan (AX) and cellulose were extracted from wheat straw, whereas starch was extracted from potato peel. Thereafter, cellulose and starch were esterified with lauric, myristic, palmitic and stearic acids to prepare corresponding cellulose (CFAs) and starch fatty acid esters (SFAs) with DS 2.1–2.8. XRD study revealed remarkable loss of crystallinity in cellulose and starch due to fatty acid ...
DOI:
10.1016/j.carbpol.2021.118317

5. Puerarin inhibited 3-chloropropane-1,2-diol fatty acid esters formation by reacting with glycidol and glycidyl esters

Author:
Ru Wang; Mengru Tao; Yamin Zhu; Daming Fan; Mingfu Wang; Yueliang Zhao
Source:
Food chemistry 2021 v.358 pp. 129843
ISSN:
0308-8146
Subject:
antioxidant activity; chemical structure; fatty acids; food chemistry; glycidol; palm oils; polyphenols; potatoes
Abstract:
... The inhibitory effects of seven polyphenols on 3-chloropropane-1,2-diol fatty acid esters (3-MCPDE) formation were investigated in palm oil models. Results showed that there was not a positive significant correlation between the free-radical scavenging activities of the tested compounds and their 3-MCPDE-formation inhibitory activities; puerarin, with weak antioxidant activity, showed the highest ...
DOI:
10.1016/j.foodchem.2021.129843

6. Dietary exposure of general Chinese population to fatty acid esters of 3-monochloropropane-1, 2-diol (3-MCPD) from edible oils and oil-containing foods

Author:
Xia Cui; Lei Zhang; Pingping Zhou; Zhaoping Liu; Sai Fan; Dajin Yang; Jianwen Li; Qing Liu
Source:
Food additives & contaminants 2021 v.38 no.1 pp. 60-69
ISSN:
1944-0057
Subject:
acceptable daily intake; alpha-chlorohydrin; cooking fats and oils; dietary exposure; fatty acids; food contamination; food intake; gas chromatography-mass spectrometry; gender; information systems; models; risk; China
Abstract:
... Edible oils and oil-containing foods have been regarded as the main source of 3-monochloropropane-1, 2-diol (3-MCPD) esters. A total of 3,847 individual food samples were collected in China to carry out 3-MCPD fatty acid esters analysis. The samples comprising edible oils, fried foods and bakery foods from 31 Chinese provinces, municipalities and autonomous regions were obtained from the national ...
DOI:
10.1080/19440049.2020.1834151

7. Improvements on the Phenylboronic Acid Derivatization Method in Determination of 3-monochloropropane Fatty Acid Esters in Camellia Oil by N-(n-propyl)ethylenediamine Solid Phase Extraction

Author:
Liqun Zhang; Leyi Wu; Pinggu Wu
Source:
Food analytical methods 2021 v.14 no.4 pp. 797-804
ISSN:
1936-9751
Subject:
Camellia; absorption; alpha-chlorohydrin; derivatization; ethylenediamines; fatty acids; food safety; oils; phenylboronic acids; pollution; solid phase extraction; standard deviation
Abstract:
... Pollution of foods with chloropropanol fatty acid esters is a growing international food safety issue, especially contamination with 3-monochloropropane-1, 2-diol (3-MCPD) esters. Traditional GC/MS method using phenylboronic acid (PBA) as a derivatization reagent has been proven to be high selective. However, the disadvantage of this method is that excessive amounts of phenylboronic acid causes ...
DOI:
10.1007/s12161-020-01944-8

8. Discovery and development of a novel short-chain fatty acid ester synthetic biocatalyst under aqueous phase from Monascus purpureus isolated from Baijiu

Author:
Youqiang Xu; Xiaocheng Wang; Xiao Liu; Xiuting Li; Chengnan Zhang; Weiwei Li; Xiaotao Sun; Wenhua Wang; Baoguo Sun
Source:
Food chemistry 2021 v.338 pp. 128025
ISSN:
0308-8146
Subject:
fatty acid esters,   etc   ; DNA libraries; Monascus purpureus; biocatalysts; fermentation; flavor; food chemistry; food industry; genome; hydrolases; octanoic acid; short chain fatty acids; synthesis; transcriptome; ultrasonics;     Show all 15 Subjects
Abstract:
... Short-chain fatty acid esters are important flavor chemicals in Chinese traditional fermented Baijiu. Monascus purpureus was recognized as an important microorganism contributing to ester synthesis. However, the molecular basis for ester synthesis was still lacking. The present work combined genome sequencing, transcriptome sequencing, gene library construction, and enzyme engineering to discover ...
DOI:
10.1016/j.foodchem.2020.128025

9. Esterification of anthocyanins isolated from floral waste: Characterization of the esters and their application in various food systems

Author:
Sandesh J. Marathe; Nirali N. Shah; Seema R. Bajaj; Rekha S. Singhal
Source:
Food bioscience 2021 v.40 pp. 100852
ISSN:
2212-4292
Subject:
fatty acid esters,   etc   ; acetonitrile; acylation; anthocyanins; antioxidant activity; assays; carboxylic ester hydrolases; citric acid; color; corolla; cream; dodecanoic acid; dyes; esterification; extraction; functional foods; heat treatment; lipid peroxidation; lipophilicity; resins; rice; solvents; wastes;     Show all 23 Subjects
Abstract:
... resins. Acylated anthocyanins were primarily detected using TLC followed by confirmation using LC-MS analysis. Optimization of the reaction parameters was carried out by one-factor-at-a-time method using HPTLC. An optimized molar conversion of 63% of anthocyanins to its fatty acid esters was achieved in acetonitrile at 40 °C with a cyanidin:lauric acid molar ratio of 1:100 and an enzyme and molecular ...
DOI:
10.1016/j.fbio.2020.100852

10. New unsaturated fatty acids from the aerial parts of Lycopodiastrum casuarinoides

Author:
Yang Liu; Xiao-Chang Yao; Jing Li; Zhen-Xing Zou; Chen Xi; Kang-Ping Xu; Feng-Hua Kang; Ping-Sheng Xu; Gui-Shan Tan
Source:
Phytochemistry letters 2021 v.41 pp. 55-60
ISSN:
1874-3900
Subject:
fatty acid esters,   etc   ; acetylcholinesterase; aerial parts; cholinesterase; literature; plant biochemistry; spectral analysis; unsaturated fatty acids;     Show all 8 Subjects
Abstract:
... Two new unsaturated fatty acid esters (1 and 2) and five new unsaturated fatty acids (4–8), together with two known analogs (3 and 9) were isolated from the aerial parts of Lycopodiastrum casuarinoides. Their structures were unambiguously elucidated by obtaining extensive spectroscopic data and comparing them with data in the literature. The absolute configurations of 1 and 2 were established ...
DOI:
10.1016/j.phytol.2020.11.004

11. Urinary Excretion of 2/3‐Monochloropropanediol (2/3‐MCPD) and 2,3‐Dihydroxypropylmercapturic Acid (DHPMA) after a Single High dose of Fatty Acid Esters of 2/3‐MCPD and Glycidol: A Controlled Exposure Study in Humans

Author:
Klaus Abraham; Jan Hielscher; Jan Kuhlmann; Bernhard H. Monien
Source:
Molecular nutrition & food research 2021 v.65 no.4 pp. e2000735
ISSN:
1613-4125
Subject:
alpha-chlorohydrin; biomarkers; body weight; excretion; fatty acids; food research; glycidol; half life; hazelnut oil; hydrolysis; intestines; metabolites; nutrition; stomach
Abstract:
... SCOPE: 2‐ and 3‐monochloropropanediol (2/3‐MCPD) and glycidol are absorbed in the intestine after lipase‐catalyzed hydrolysis of their fatty acid esters. METHODS AND RESULTS: In an exposure study with 12 non‐smoking participants, the complete urinary excretion of the metabolite 2,3‐dihydroxypropylmercapturic acid (DHPMA) and of 2/3‐MCPD is measured on four consecutive days before and after ...
DOI:
10.1002/mnfr.202000735

12. Dietary exposure to fatty acid esters of monochloropropanediols and glycidol of 2- to 3-year-old children attending nursery schools from two areas in China using the duplicate-diet collection method

Author:
Liang Jiang; Zhou Jing; Wang Yibaina; Song Yan; Xu Lili; Zhong Yanxu; Yong Ling; Zhou Pingping; Sui Haixia; Zhang Lei
Source:
Food additives & contaminants 2021 v.38 no.1 pp. 70-80
ISSN:
1944-0057
Subject:
alpha-chlorohydrin; diet; dietary exposure; esterification; fatty acids; glycidol; risk; China
Abstract:
... The dietary exposures to fatty esters of 3- and 2-monochloropropanediol (MCPD) and glycidol were estimated for children aged 2- to 3-year-old from two areas of China using duplicate diet collection method. The 24-h daily duplicate diet samples over three consecutive days were collected from 40 healthy children aged between 26 and 36 months. The analysis of these contaminates in food samples was me ...
DOI:
10.1080/19440049.2020.1843718

13. A novel molecular tube fully modified at one end: selective inclusion of cis-unsaturated fatty acid esters

Author:
Chizuru Kogame-Asahara; Shogo Ito; Hitomi Iguchi; Ai Kazama; Hajime Shigemitsu; Toshiyuki Kida
Source:
Chemical communications 2020 v.56 no.9 pp. 1353-1356
ISSN:
1364-548X
Subject:
fatty acid esters,   etc   ; beta-cyclodextrin; chemical reactions; organosilicon compounds;     Show all 4 Subjects
Abstract:
... A novel cyclodextrin molecular tube with one fully modified and one unmodified end was facilely synthesized by selective desilylation of a 6-O-tert-butyldimethylsilylated β-cyclodextrin dimer possessing multiple linkers. This molecular tube showed a selective inclusion ability toward cis-unsaturated fatty acid esters by utilizing the asymmetric cylindrical nanocavity. ...
DOI:
10.1039/c9cc08709e

14. Are chloropropanols and glycidyl fatty acid esters a matter of concern in palm oil?

Author:
Tânia Gonçalves Albuquerque; Helena S. Costa; Mafalda Alexandra Silva; M. Beatriz P.P. Oliveira
Source:
Trends in food science & technology 2020 v.105 pp. 494-514
ISSN:
0924-2244
Subject:
European Union; attitudes and opinions; chlorides; chromatography; deodorization; diacylglycerols; food industry; food matrix; foods; frying; laws and regulations; mass spectrometry; mutagens; public health; refining; temperature; toxicity; vegetable oil
Abstract:
... Palm oil is the most consumed worldwide, being evident its importance due to several applications by the food industry. The presence of toxic and mutagenic compounds, such as chloropropanols and glycidyl fatty acid esters has increased the attention on this oil. Very recently, there have been several alerts about the safety of certain foods containing palm oil in their composition. Consequently ...
DOI:
10.1016/j.tifs.2019.01.005

15. Contamination of some foodstuffs marketed in Italy by fatty acid esters of monochloropropanediols and glycidol

Author:
Eleonora Di Campi; Mauro Di Pasquale; Ettore Coni
Source:
Food additives & contaminants 2020 v.37 no.5 pp. 753-762
ISSN:
1944-0057
Subject:
fatty acid esters,   etc   ; adverse effects; alpha-chlorohydrin; biscuits; breads; breakfast cereals; cookies; crackers; derivatization; esterification; frying; gas chromatography-mass spectrometry; glycidol; ingredients; margarine; olive oil; palm oils; potato chips; seed oils; Italy;     Show all 20 Subjects
Abstract:
... Fatty acid esters of 3-monochloropropanediol (3-MCPD), 2-MCPD and glycidol (Gly) are food-processing contaminants that cause concerns about possible adverse health effects. The present study evaluates the contamination levels of the three ester classes in 130 samples of foodstuffs marketed in Italy covering 10 food categories, namely margarines, oils, roasted coffee, breakfast cereals, salted ...
DOI:
10.1080/19440049.2020.1725146

16. The effect of extractive lacto-fermentation on the bioactivity and natural products content of Pittosporum angustifolium (gumbi gumbi) extracts

Author:
Snezana Agatonovic-Kustrin; Vladimir Gegechkori; David W. Morton
Source:
Journal of chromatography 2021 v.1647 pp. 462153
ISSN:
0021-9673
Subject:
Pittosporum angustifolium; alpha-amylase; anti-inflammatory activity; antioxidant activity; antioxidants; derivatization; enzyme inhibition; lactic fermentation; lignin; medicine; nitric oxide; nitrogen; polyphenols; saturated fatty acids; thin layer chromatography
Abstract:
... that inhibits α-amylase, suggests that fatty acid esters are responsible for the enzyme inhibition; both saturated fatty acid esters in unfermented extracts and unsaturated fatty acid esters in fermented extracts. The ATR-FTIR spectra of the polyphenolics in fermented extracts (RF = 0.15-0.20) suggests the presence of soluble lignin fragments (i.e. lignins depolymerized into monomers and oligomers during ...
DOI:
10.1016/j.chroma.2021.462153

17. Metabolites of 2‐ and 3‐Monochloropropanediol (2‐ and 3‐MCPD) in Humans: Urinary Excretion of 2‐Chlorohydracrylic Acid and 3‐Chlorolactic Acid after Controlled Exposure to a Single High Dose of Fatty Acid Esters of 2‐ and 3‐MCPD

Author:
Nick Bergau; Zhiyong Zhao; Klaus Abraham; Bernhard H. Monien
Source:
Molecular nutrition & food research 2021 v.65 no.4 pp. e2000736
ISSN:
1613-4125
Subject:
aerobiosis; alpha-chlorohydrin; biomarkers; deodorization; excretion; fatty acids; food research; hazelnut oil; humans; hydrolysis; intestines; metabolites; nutrition; urine; vegetables
Abstract:
... SCOPE: Fatty acid esters of 2‐monochloropropane‐1,3‐diol (2‐MCPD) and 3‐monochloropropane‐1,2‐diol (3‐MCPD) are formed during the deodorization of vegetable oils. After lipase‐catalyzed hydrolysis in the intestine, 2‐ and 3‐MCPD are absorbed, but their ensuing human metabolism is unknown. METHODS AND RESULTS: The compounds 2‐chlorohydracrylic acid (2‐ClHA) and 3‐chlorolactic acid (3‐ClLA ...
DOI:
10.1002/mnfr.202000736

18. Controlling reaction selectivity for sugar fatty acid ester synthesis by using resins with different basicities

Author:
Tomone Sasayama; Ayumu Kanezawa; Kousuke Hiromori; Atsushi Takahashi; Naomi Shibasaki-Kitakawa
Source:
Food chemistry 2021 v.340 pp. 128100
ISSN:
0308-8146
Subject:
fatty acid esters,   etc   ; catalysts; catalytic activity; food chemistry; ion exchange; knowledge; mass transfer; selectivity (chemistry); sugars; surfactants; synthesis; transesterification;     Show all 12 Subjects
Abstract:
... A strongly basic ion-exchange resin catalyst was reported to exhibit a high catalytic activity in transesterification to produce a bio-based surfactant, sugar ester under mild condition. However, the side-reactions to decompose the reactant and the product were found to occur. This study was aimed to improve the selectivity of sugar ester synthesis by newly focusing on the basicity of the resin. A ...
DOI:
10.1016/j.foodchem.2020.128100

19. Autolysis‐mediated membrane vesicle formation in Bacillus subtilis

Author:
Kimihiro Abe; Masanori Toyofuku; Nobuhiko Nomura; Nozomu Obana
Source:
Environmental microbiology 2021 v.23 no.5 pp. 2632-2647
ISSN:
1462-2912
Subject:
fatty acid esters,   etc   ; Bacillus subtilis; autolysis; biogenesis; cell membranes; cell viability; cold stress; gametolysin; hypoxia; microbiology; starvation; sucrose; surfactants;     Show all 13 Subjects
Abstract:
... It is known that Bacillus subtilis releases membrane vesicles (MVs) during the SOS response, which is associated with cell lysis triggered by the PBSX prophage‐encoded cell‐lytic enzymes XhlAB and XlyA. In this study, we demonstrate that MVs are released under various stress conditions: sucrose fatty acid ester (SFE; surfactant) treatment, cold shock, starvation, and oxygen deficiency. B ...
DOI:
10.1111/1462-2920.15502

20. Solvent-free synthesis of phytosterol linoleic acid esters at low temperature

Author:
Wei Liu; Bing Xiao; Xiaoping Wang; Jingnan Chen; Guolong Yang
Source:
RSC advances 2021 v.11 no.18 pp. 10738-10746
ISSN:
2046-2069
Subject:
catalysts; equipment; esterification; food industry; hydrolysis; hydrophobicity; linoleic acid; phytosterols; solubility; soybeans; temperature; vegetables
Abstract:
... Phytosterol unsaturated fatty acid esters show much higher oil solubility than free phytosterol. Thus, development of a green and low-cost method for the preparation of phytosterol fatty acid esters is highly desirable in the food industry. Herein, we have developed a simple chemical method toward efficient preparation of phytosterol linoleic acid esters at very mild temperature (60 °C) using 4 ...
DOI:
10.1039/d1ra00798j