Monday, May 4, 2015

Brewing Up Shikimic Acid

Could preparing Tamiflu starters be as simple as making your morning cappuccino?

The lab instrument in question,
straight from the Supporting Info
(I <3 pictures in SI)
Jason Smith and coworkers from the University of Tasmania have reported a PHWE - pressurized hot water extraction - to obtain shikimic acid, a common starting material in several routes to oseltamivir phosphate (Tamiflu). In a preparation that begs repetition, they grind up up 20 g of Chinese star anise, mix with sand, and quickly wash with a hot ethanol-water mixture using a household espresso maker (see right).

The researchers claim that, after a quick silica plug, they obtain 5.5% (w/w) of "sufficiently pure"* shikimic acid. I'd encourage you to go see the NMR spectra for yourself.

Of course, pressing common kitchen tools into synthetic service isn't news. My undergraduate lab group ordered many of its smaller-bore funnels and spatulae from a kitchen supply store. And let's not forget grindstone chemistry, popularized by the late Ajay Bose at the Stevens Institute of Technology, which used a stainless-steel blender** to combine solid reagents into heterocycles.

If molecular gastronomy involves bringing the techniques of organic and biochemistry into the kitchen, perhaps this represents its antipode, some sort of 'reverse' molecular gastronomy in which kitchen appliances and techniques inform bench science. Makes perfect sense; after all (say it with me)...Chemistry is Just Like Cooking!

*Based on the 1H NMR, I'm guessing their material hovers around 90% pure. Still good, given a 2-minute prep time. 
**Kitchen-Aid, no less - high-quality 'instruments' for high-quality chemistry : )


  1. Per endnote 21

    (21) A Breville espresso machine model 800ES, available for

    $300 from retail outlets such as Amazon, was used.

  2. I saw this paper yesterday and had a good laugh and had to show it everyone in our group: of course expresso machine as high-efficiency extractor is so obvious, except that no-one saw it before. Also, their lab must have smelled rather wonderful, like chai.

    I wonder what is next: using a toaster oven instead of a hotplate, for baking TLCs ?

    1. I'll race you to the appliance section!

    2. while the expresso extraction may not find much use in a synthetic lab, it would be an excellent choice for improvised extraction of crushed pills, in order to make them injectable

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