A Two-Step Process for the Synthesis of Hydroxytyrosol

ChemSusChem
Paolo ZiosiPaolo Righi

Abstract

A new process for the synthesis of hydroxytyrosol (3,4-dihydroxyphenylethanol), the most powerful natural antioxidant currently known, by means of a two-step approach is reported. Catechol is first reacted with 2,2-dimethoxyacetaldehyde in basic aqueous medium to produce the corresponding mandelic derivative with >90 % conversion of the limiting reactant and about 70 % selectivity to the desired para-hydroxyalkylated compound. Thereafter, the intermediate is hydrogenated to hydroxytyrosol by using a Pd/C catalyst, with total conversion of the mandelic derivative and 68 % selectivity. This two-step process is the first example of a synthetic pathway for hydroxytyrosol that does not involve the use of halogenated components or reduction methodologies that produce stoichiometric waste. It also avoids the complex procedure currently used for hydroxytyrosol purification when it is extracted from wastewater of olive oil production.

References

Jun 24, 1998·Biochemical and Biophysical Research Communications·F VisioliC Galli
Feb 7, 2001·Journal of Agricultural and Food Chemistry·M Esti La Notte E
Jul 7, 2000·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·R W OwenH Bartsch
Jul 26, 2000·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·R W OwenH Bartsch
Dec 18, 2001·Medicinal Research Reviews·Francesco VisioliClaudio Gall
Mar 22, 2002·The Lancet Oncology·R W OwenH Bartsch
Jan 29, 2003·The Journal of Nutritional Biochemistry·Kellie L. Tuck, Peter J. Hayball
May 28, 2004·European Journal of Clinical Nutrition·M N VissersM B Katan
Oct 26, 2005·Waste Management·A RoigM A Sánchez-Monedero
Sep 26, 2006·Journal of Chemical Information and Modeling·Zoran MarkovićNebojsa Begović
Apr 7, 2007·Journal of Agricultural and Food Chemistry·Augusto GambacortaAntonella Migliorini
May 15, 2007·Journal of Agricultural and Food Chemistry·Samia AzabouSami Sayadi
Oct 26, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alessandra BendiniGiovanni Lercker
Jul 18, 2008·Chemical Communications : Chem Comm·Roger A Sheldon
Sep 6, 2008·Journal of Agricultural and Food Chemistry·Roberta BerniniFernanda Crisante
Dec 25, 2010·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·Fatemeh MohagheghiMarzyeh Rashidi Pour
Feb 8, 2011·Bioresource Technology·Jean-Michel LavoieMathieu Bilodeau
Aug 4, 2012·Bioresource Technology·R BeauchetJ M Lavoie

❮ Previous
Next ❯

Citations

Sep 22, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ping-Chen TuYueh-Hsiung Kuo
Sep 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Amalia D KalampalikiIoannis K Kostakis
Jun 10, 2019·Applied Microbiology and Biotechnology·James BrittonKevin E O'Connor
Jun 1, 2021·Angewandte Chemie·Simona PompeiWolfgang Kroutil
Dec 17, 2019·The Journal of Organic Chemistry·Martin J WannerJan H van Maarseveen

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

World Review of Nutrition and Dietetics
D Boskou
Ugeskrift for laeger
P Marckmann, A V Astrup
World Review of Nutrition and Dietetics
D Boskou
Rassegna di dermatologia e di sifilografia
G GARDENGHI
© 2022 Meta ULC. All rights reserved