Ithaca College

Chemistry and Biochemistry students Noah Budin, Erin Higgins, Anthony DeBernardo and Cassidy Raab along with Chemistry staff member Chun Li and faculty member Scott Ulrich published a paper in Bioorganic Chemistry titled: “Efficient synthesis of the ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer.”  https://www.sciencedirect.com/science/article/pii/S0045206818304784

 Ketone bodies are produced from fats under glucose deprivation conditions, such as fasting or adherence to a high fat/low carbohydrate “ketogenic” diet. The ketogenic diet is an effective and widely used epilepsy treatment and may be useful for a variety of other neurological conditions. Ketone body esters are nutritional supplements that induce ketosis while on a normal diet, and have significant promise to replace the ketogenic diet for treating medical conditions that respond to ketosis. They have also been shown to improve human athletic performance, as highlighted in a recent article in The Atlantic: https://www.theatlantic.com/health/archive/2017/11/keto-in-a-bottle/545129/. 

This paper describes a new synthesis of the ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer using a short, operationally simple sequence starting from inexpensive racemic β-butyrolactone. This synthetic method will make the ketone body ester widely available to study its use in treating medical conditions and enhancement of human athletic performance.