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Circa Group Pty Ltd
Bio21 Molecular Science
& Biotechnology Institute
30 Flemington Road, Parkville
VIC 3052 Australia
Twitter @circagroup

Tony Duncan
Chief Executive Officer
Tony.Duncan@circagroup.com.au

Fabien Deswarte
Business Development Manager
Fabien.Deswarte@circasc.com

c/o Bio 21, Flemington Road
Melbourne
Australia

+61 419 303 117

Circa Group is converting waste biomass into advanced biochemical materials.

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Cyrene

 

Cyrene is Circa’s trade name for (-)-dihydrolevoglucosenone (1S,5R)-6,8-Dioxabicyclo[3.2.1]octan-4-one; CAS Reg. No. 53716-82-8

General properties overview:

Stability in the Presence of Bases

Cyrene is a cyclic ketone containing two protons alpha to the carbonyl group and, like cyclohexanone, it will form initially dimers and then oligomers and insoluble polymers when treated with strong bases such as sodium hydroxide, potassium carbonate and many strongly basic organic amines. Cyrene is however unchanged by heating in chloroform in the presence of triethylamine at 60oC for 18 hours.

Stability in the Presence of Acids

Cyrene is relatively stable in the presence of weak acids and, for example, can be heated with trifluoracetic acid at 60oC for 18h without apparent change. Brief treatment with aqueous 2M HCl however rapidly converts Cyrene to a mixture of products that have not yet been characterised.

Stability to Oxidizing Agents

Cyrene reacts violently with 30% aqueous hydrogen peroxide at room temperature. It will react selectively with hydrogen peroxide and peracids, such as peracetic and m-chloroperbenzoic acid under carefully controlled conditions to afford a mixture of (5S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone and its formyl ester. Reactivity with other strong oxidants has not been tested and caution should be exercised whenever doing so in view of the violence of the reaction with 30% hydrogen peroxide.

Other Reactions of Cyrene™

Because dihydrolevoglucosenone has only been available in useful quantities quite recently, its chemistry remains relatively unexplored. Some useful recent investigations of the reactivity and solvent properties of Cyrene have been published by Clark et al and by Greatrex and co-workers.


Romero et al, Ind. Eng. Chem. Res., (2013), 52, 2257

Allais, F. et al, Green Chem., (2015), 17, 404

Clark, J. H. et al, Chem Commun., (2014), 50, 9650

Greatrex, B. W. et al, Eur. J. Org. Chem., (2015), 6999



New frontiers in sustainable membrane preparation: Cyrene™ as green bioderived solvent

T. Marino, F. Galian, A Molino, A Figoli


Official advice we’ve received our REACH Annex VIII accreditation


Toxicity screening of potential bio-based Polar Aprotic Solvents

 

Research

Soybean hulls, an alternative source of bioactive compounds: Combining pyrolysis with bioguided fractionation


Cyrene as a bio-based alternative for dipolar aprotic solvents

James Sherwood, Mario De Bruyn, Andri Constantinou, Laurianne Moity, C. Rob McElroy, Thomas J. Farmer, Tony Duncan, Warwick Raverty, Andrew J. Hunt and James H. Clark, 2014

Dihydrolevoglucosenone (Cyrene) is a bio-based molecule, derived in two simple steps from cellulose, which demonstrates significant promise as a dipolar aprotic solvent.


USING CYRENE AS A REPLACEMENT FOR DMF IN SONOGASHIRA CROSS-COUPLING AND CACCHI- TYPE ANNULATIONS

Kirst L. Wilson, Alan R. Kennedy, Jane Murray, Ben Greatrex, Craig Jamieson and Allan J. B. Watson


Green and Sustainable Solvents in Chemical Processes

Coby J. Clarke, Wei-Chien Tu, Oliver Levers, Andreas Bröhl, and Jason P. Hallett

Department of Chemical Engineering, Imperial College, London SW7 2AZ, United Kingdom


Cyrene as a bio-based solvent for HATU mediated amide coupling

Kirsty L Wilson, Jane Murray, Craig Jamieson and Allan J. B. Watson


Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization

Parijat Ray, Timothy Hughes, Craig Smith, George P. Simon and Kei Saito,

Department of Materials Science and Engineering and New Horizons Research Centre and ‡ School of Chemistry, Monash University, Clayton, Victoria, Australia


Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through retro-aza-Michael//aza-Michael Isomerizations

Tsai YH, Borini Etichetti CM, Di Benedetto C, Girardini JE, Martins FT, Spanevello RA, Suárez AG, Sarotti AM


Method for synthesizing a precursor
of a single Dairy-Lactone Isomer

Florent Allais, Aurélien Peru, Ben Greatrex, Douglas Warwick, Anthony Duncan


Bio‐based Chiral Amines via Aza‐Michael Additions to (‐)‐Levoglucosenone Under Aqueous Conditions

John Sperry, Ben Greatrex, Shinji Kudo, Shi-Wei Kim, Ed Ledingham

Institut des Science et Industries du Vivant et de L'environnement-Agroparis Tech, University of New England, Circa Group PTY LTD


Oxygenated commodity chemicals from chemo‐catalytic conversion of biomass derived heterocycles

Siddarth H. Krishna, Kefeng Huang, Kevin J. Barnett, Jiayue He, Christos T. Maravelias, James A. Dumesic, George W. Huber, Mario De bruyn, Bert M. Weckhuysen


The Green Transformation of Solid-Phase Peptide Synthesis


FABRICATION OF PES/PVP MEMBRANES USING CYRENE


Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation



Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives


Identification of high performance solvents for the sustainable processing of graphene


Synthesis of ureas in the bio-alternative solvent Cyrene


Cyrene as a Bio-Based Solvent for the Suzuki–Miyaura Cross-Coupling


Greener solvents for solid-phase synthesis


Concise and efficient synthesis of E-stereoisomers of exo-cyclic carbohydrate enones. Aldol condensation of dihydrolevoglucosenone with five-membered aromatic aldehydes


Cross-aldol reactions of levoglucosenone and its derivatives with cyclohex-1-en-1-ol ethers


Organic solvent- and catalyst-free Baeyer–Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene®): a sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone


Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications


One-pot synthesis of carbohydrate exo-cyclic enones and hemiketals with 6,8-dioxabicyclo-[3.2.1]octane moieties. Serendipitous formation of a spironolactone when 2-pyridinecarboxaldehyde is used as the reactant


Synthesis of a Chiral Auxiliary Family from Levoglucosenone and Evaluation in the Diels–Alder Reaction


Development of pharmaceutically relevant bio-based intermediates though aldol condensation and Claisen–Schmidt reactions of dihydrolevoglucosenone (Cyrene®)


Sustainable production of highly conductive multilayer graphene ink for wireless connectivity and IoT applications



Vapor pressures, densities, and PC-SAFT parameters for 11 bio-compounds


Bio-Inspired Robust Membranes Nanoengineered from Interpenetrating Polymer Networks of Polybenzimidazole/Polydopamine



New frontiers in sustainable membrane preparation: Cyrene™ as green bioderived solvent



Tailoring the Performance of Organic Solvent Nanofiltration Membranes with Biophenol Coatings


Solvent effects in palladium catalysed cross-coupling reactions


A Method of Calculating the Kamlet–Abboud–Taft Solvatochromic Parameters Using COSMO-RS


Preparation of the diastereomerically pure 2S-hydroxy derivative of dihydrolevoglucosenone (cyrene)


Development of bio-acrylic polymers from Cyrene™: transforming a green solvent to a green polymer



Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™