Relationship structure-antioxidant activity of hindered phenolic compounds

Authors

  • X. C. Weng School of Life Sciences, Shanghai University
  • Y. Huang School of Life Sciences, Shanghai University

DOI:

https://doi.org/10.3989/gya.0225141

Keywords:

DPPH, Hindered phenolic, Rancimat test, Steric synergist effect, Structure activity relationship

Abstract


The relationship between the structure and the antioxidant activity of 21 hindered phenolic compounds was investigated by Rancimat and DPPH· tests. 3-tert-butyl-5-methylbenzene-1,2-diol is the strongest antioxidant in the Rancimat test but not in the DPPH· test because its two hydroxyl groups have very strong steric synergy. 2,6-Ditert-butyl-4-hydroxy-methylphenol exhibits a strong antioxidant activity as 2,6-ditertbutyl- 4-methoxyphenol does in lard. 2,6-Ditert-butyl-4- hydroxy-methylphenol also exhibits stronger activity than 2-tert-butyl-4- methoxyphenol. The methylene of 2,6-ditert-butyl-4-hydroxy-methylphenol can provide a hydrogen atom to active free radicals like a phenolic hydroxyl group does because it is greatly activated by both the aromatic ring and hydroxyl group. Five factors affect the antioxidant activities of the phenolic compounds: how stable the phenolic compound free radicals are after providing hydrogen atoms; how many hy drogen atoms each of the phenolic compounds can provide; how fast the phenolic compounds provide hydrogen atoms; how easily the phenolic compound free radicals can combine with more active free radicals, and whether or not a new antioxidant can form after the phenolic compound provides hydrogen atoms.

Downloads

Download data is not yet available.

References

Bonde V, Brand WW, Berset C. 1997. Kinetics and Mechanisms of Antioxidant Activity using the DPPH· Free Radical Method. LWT-Food Sci. Technol. 30, 609–615.

Burton GW, Ingold KU. 1986. Vitamin E: applications of the principles of physical organic chemistry to exploration of its structure and function. Acc. Chem. Res. 19, 194–201. http://dx.doi.org/10.1021/ar00127a001

Burton GW, Doba T, Gabe E, Hughes L, Lee FL, Prasad L, Ingold KU. 1985. Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols. J. Am. Chem. Soc. 107, 7053–7065. http://dx.doi.org/10.1021/ja00310a049

Burton GW. 1980. Antioxidant activity of vitamin E and related phenols. Importance of stereoelectronic factors. J. Am. Chem. Soc. 102, 7791–7792. http://dx.doi.org/10.1021/ja00546a032

Burton GW, Ingold KU. 1981. Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. J. Am. Chem. Soc. 103, 6472–6477. http://dx.doi.org/10.1021/ja00411a035

Burton GW, Hughes L, and Ingold KU. 1983. Antioxidant activity of phenols related to vitamin E. Are there chainbreaking antioxidants better than α-tocopherol? J. Am. Chem. Soc. 105, 5950–5951. http://dx.doi.org/10.1021/ja00356a057

Cao GF, Weng XC. 1995. Study of oxidation stability of fish oil. China Oils Fats. 20, 44–46.

Duan S, Weng XC, Dong XW, Liu YP, Li HP, Jin JR. 1998. Antioxidant Properties of Butylated-hydroxytoluene Refluxed in Ferric Chloride Solution. Food Chem. 61, 101–105. http://dx.doi.org/10.1016/S0308-8146(97)00122-2

Fossey J, Lefort D, Sorba J. 1995. 4-Radical Stability, in Free Radicals in Organic Chemistry, John Wiley & Sons, New York, 31–38.

Gordon MH, Mursi E. 1994. A comparison o f oil stability based on the Metrohm Rancimat with storage at 20 C. J. Am. Oil Chem. Soc. 71, 649–651. http://dx.doi.org/10.1007/BF02540595

Gordon MH. Weng XC. 1992. Antioxidant Activity of Quinones Extracted from Tanshen (Salvia miltiorrhiza Bunge). J. Agric. Food Chem. 40, 1331–1338. http://dx.doi.org/10.1021/jf00020a007

Guo JN, Weng XC, Wu H, Li QH, Bi KS. 2005. Antioxidants from a Chinese medicinal herb –Psoralea corylifolia L-. Food Chem. 91, 287–292. http://dx.doi.org/10.1016/j.foodchem.2004.04.029

Huang Y, Jiang ZW, Liao XY, Hou JP, Weng XC. Antioxidant activities of two novel synthetic methylbenzenediol derivatives. Czech Journal of Food Science.

Läubli MW, Bruttel PA. 1986. Determination of the oxidative stability of fats and oils: comparison between the active oxygen method (AOCS Cd 12–57) and the Rancimat method. J. Am. Oil Chem. Soc. 63, 792–795. http://dx.doi.org/10.1007/BF02541966

Läubli MW, Brutte l PA, Schalch E. 1988. Determination of the Oxidative Stability of Fats and Oils. Comparison Between the Active Oxygen Method AOM and Rancimat Method, Fat Sci. Technol. 90, 56–58.

Lebeau J, Furman C, Bernier JL, Duriez P, Teissier E, Cotelle N. 2000. Antioxidant properties of di-tert-butylhydroxylated flavonoids. Free Radical Biol. Medicine. 29, 900–912. http://dx.doi.org/10.1016/S0891-5849(00)00390-7

Li JY, Wang T, Wu H, Ho CT, Weng XC. 2006. 1,1-di-(2',5'- dihydroxy-4' -tert-butylphenyl)ethane: a novel antioxidant. J. Food Lipids. 13, 331–340. http://dx.doi.org/10.1111/j.1745-4522.2006.00056.x

Lucarini M. 1996. Bond Dissociation Energies of O-H Bonds in Substituted Phenols from Equilibration Studies. J. Org. Chem. 61, 9259–9263. http://dx.doi.org/10.1021/jo961039i

Mensor LL, Menezes FS, Leitao GG, Reis AS, Santos TC, Coube CS, Leitao SG. 2001. Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method. Phytoth. Research. 15, 127–130. http://dx.doi.org/10.1002/ptr.687 PMid:11268111

Philip M. 2004. The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J. Sci. Technol. 26, 211–219.

Pokorny J, Yanishieva N, Gordon MH. 2001. Antioxidants in food. In J. Pokorny (Eds.), Practical Applications (pp. 16–18). Cambridge: Woodhead Publishing Limited.

Qiu XY, Wang DH, Li JY, Weng XC. 2005. A New Parameter to Characterize Phenolic Antioxidant Activity in Elimination of DPPH·. J. Shanghai Univer. (Natural Science). 206–211.

Slater JC. 1964. Atomic Radii in Crystals. J. Chem. Physics. 41, 3199. http://dx.doi.org/10.1063/1.1725697

Wang W, Weng XC, Cheng DL. 2000. Antioxidant activities of natural phenolic components from Dalbergia odorifera T. Food Chem. 71, 45–49. http://dx.doi.org/10.1016/S0308-8146(00)00123-0

Weng XC. 1993. Antioxidants and Antioxidant Mechanism. J. Zhengzhou Grain College. 19, 20–29.

Weng XC, Wu H. 2000. Determination Methods and the Evaluation of Antioxidant Activity. China Oils Fats. 25 119–122.

Wright JS, Johnson ER and DiLabio GA. 2001.Predicting the Activity of Phenolic Antioxidants: Theoretical Method, Analysis of Substituent Effects, and Application to Major Families of Antioxidants. J. Am. Chem. Soc. 123, 1173–1183. http://dx.doi.org/10.1021/ja002455u PMid:11456671

Zhang CX, Wu H, Weng XC. 2004. Two novel synthetic antioxidants for deep frying oils. Food Chem. 84, 219–22. http://dx.doi.org/10.1016/S0308-8146(03)00205-X

Zhang HY. 1998. Selection of theoretical parameter characterizing scavenging activity of antioxidants on free radicals. J. Am. Oil Chem. Soc. 75, 1705–1709. http://dx.doi.org/10.1007/s11746-998-0320-4

Zhang HY. 1999a. Investigation on effectiveness of HOMO to characterize antioxidant activity. J. Am. Oil Chem. Soc. 76, 1109—1110.

Zhang HY, Ge N, Zhang ZY. 1999. Theoretical elucidation of activity differences of five phenolic antioxidants. Acta Pharmacol. Sin. 20, 363–66.

Zhang HY. 1999b. Theoretical methods used in elucidating activity differences of phenolic antioxidants. J. Am. Oil Chem. Soc. 76, 745–48. http://dx.doi.org/10.1007/s11746-999-0170-8

Zhang HY, Chen DZ. 2000. Theoretical Elucidation on Activity Differences of Ten Flavonoid Antioxidants. 2000. Acta Biochim. Biophys. Sinica. 32, 17–321.

Zhang HY. 2000. Theoretical investigation on free radical scavenging activity of 6,7-dihydroxyflavone. Quant. Struct-Act Relat. 50, -3.

Published

2014-12-30

How to Cite

1.
Weng XC, Huang Y. Relationship structure-antioxidant activity of hindered phenolic compounds. grasasaceites [Internet]. 2014Dec.30 [cited 2022Dec.1];65(4):e051. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1516

Issue

Section

Research