NDLI: A computational study of the structure-activity relationships of some p-hydroxybenzoic acid antioxidants

Content Provider	Springer Nature Link
Author	Vafiadis, Anastasios P. Bakalbassis, Evangelos G.
Copyright Year	2003
Abstract	Equilibrium structures of all derivatized systems of p-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3-methoxy-4-hydroxybenzoic acid, and 3,5-dimethoxy-4-hydroxybenzoic acid and calculated structural and energetic molecular descriptors were determined at the B3LYP/6-31+G(d) density functional theoretical level in an attempt to study their structure-activity relationships (SAR). The theoretical antioxidant activity trend, derived in terms of hydrogen-donating capacity against radicals in lipid systems, is in excellent agreement with the experimental one. The lower antioxidant activity of benzoates, experimentally found relative to the homologous cinnamates, could be due to (i) their lower spin delocalization, (ii) their higher calculated heats of formation values in forming radicals (ΔHOF), and (iii) the much stronger electron-withdrawing effect of the-COOH group than-CH=CHCOOH. The low calculated dipole moment values of the global minimum structures of the antioxidants could facilitate their solubilities in nonpolar solvents, hence the ease of hydrogen abstraction. However, highest occupied molecular orbital (HOMO) eigenvalues can neither predict antioxidant activity nor differentiate the same activity between two series of structurally related compounds. Again, density functional theory calculations provide a good molecular descriptor, ΔHOF, to correlate with the antioxidant activity in molecules showing similar structural characteristics.
Starting Page	1217
Ending Page	1223
Page Count	7
File Format	PDF
ISSN	0003021X
Journal	Journal of the American Oil Chemists' Society
Volume Number	80
Issue Number	12
e-ISSN	15589331
Language	English
Publisher	Springer-Verlag
Publisher Date	2003-01-01
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Antioxidant B3LYP BDE DFT 3,4-dihydroxy-benzoic acid ΔHOF p-hydroxybenzoic acid 4-hydroxy-3,5-dimethoxybenzoic acid 4-hydroxy-5-methoxybenzoic acid structure-activity relationships Chemistry/Food Science Analytical Chemistry Biotechnology Industrial Chemistry/Chemical Engineering Biomaterials Agriculture
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Chemical Engineering

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

A computational study of the structure-activity relationships of some p -hydroxybenzoic acid antioxidants

Liquid-phase theoretical antioxidant activity trend of some cinnamic acid antioxidants

A density functional theory study of structure-activity relationships in caffeic and dihydrocaffeic acids and related monophenols

Theoretical methods used in elucidating activity differences of phenolic antioxidants

Synthesis, co-crystal structure and characterization of pyrazinamide with m-hydroxybenzoic acid, p-hydroxybenzoic acid and 3,4-dihydroxy benzolic acid

Synthesis and properties of lanthanide(III) complexes with 4-hydroxy-3,5-dimethoxybenzoic acid

New process for the preparation of 3,5-dihydroxy-1-pentylbenzene

In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene- 2-one Derivatives—SAR, QSAR and DFT Studies (2011)

4-hydroxy-benzoic acid (4-diethylamino-2-hydroxy-benzylidene)hydrazide: DFT, antioxidant, spectroscopic and molecular docking studies with BSA.

A computational study of the structure-activity relationships of some p-hydroxybenzoic acid antioxidants

Similar Documents

A computational study of the structure-activity relationships of some p -hydroxybenzoic acid antioxidants

Liquid-phase theoretical antioxidant activity trend of some cinnamic acid antioxidants

A density functional theory study of structure-activity relationships in caffeic and dihydrocaffeic acids and related monophenols

Theoretical methods used in elucidating activity differences of phenolic antioxidants

Synthesis, co-crystal structure and characterization of pyrazinamide with m-hydroxybenzoic acid, p-hydroxybenzoic acid and 3,4-dihydroxy benzolic acid

Synthesis and properties of lanthanide(III) complexes with 4-hydroxy-3,5-dimethoxybenzoic acid

New process for the preparation of 3,5-dihydroxy-1-pentylbenzene

In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene- 2-one Derivatives—SAR, QSAR and DFT Studies (2011)

4-hydroxy-benzoic acid (4-diethylamino-2-hydroxy-benzylidene)hydrazide: DFT, antioxidant, spectroscopic and molecular docking studies with BSA.

A computational study of the structure-activity relationships of some p-hydroxybenzoic acid antioxidants