anethole

Sambuca is an Italian anise-flavored liqueur. Its most commonly transparent white, but deep blue “black” and bright red Sambuca also exists. As with other anise liqueurs, the ouzo effect can be observed when water is added, turning it a milky white. Sambuca is flavored with essential oils obtained from anise, star anise, liquorice, and other spices. It also contains elderflowers. The oils are added to pure alcohol, sugar syrup, and other flavorings. It is commonly bottled at 42% alcohol by volume. The Molinari company states that the name Sambuca comes from an Arabic word: Zammut, an anise-flavored drink that arrived to the port of Civitavecchia by ships coming from the East. The Oxford English Dictionary states that it comes from the Latin word sambucus, meaning “elderberry”. The Greek word Sambuca was first used as the name of another elderberry liquor that was created in Civitavecchia about 130 years ago. The first commercial version started in the late 1800’s in Civitavecchia, where Luigi Manzi sold Sambuca Manzi. In 1945, soon after the end of WW2, commendatore Angelo Molinari started producing Sambuca Extra Molinari, which helped popularize Sambuca throughout Italy. 

Sambuca may be served neat. It may also be served on the rocks or with water, resulting in the ouzo effect from the anethole in the anise. It’s considered to go particularly well with coffee. Like other anise liqueurs, it may be drunk after coffee as a ammazzacaffè or added directly to coffee in place of sugar. The most iconic serving of Sambuca is a shot with 3 coffee beans, called con la mosca (“with the fly”). The 3 coffee beans are said to represent health, happiness, and prosperity, or the Holy Trinity. The shot may be ignited to toast the coffee beans with the flame extinguished immediately before drinking. Salute!

Star anise

What do star anise and flu pandemics have in common?
Sit tight, and let’s find out.

Star anise is an 8-pointed seed pod that looks like … wait for it … a star. The “anise” part of the name comes from its flavour, similar to that of the anise plant. The two aren’t actually related; they just have a that licorice-y chemical compound in common. It’s a Chinese plant, and is one of the 5 ingredients of Chinese 5 Spice mix (along with cloves, cinnamon, fennel and Sichuan pepper).

The licorice flavour comes from a chemical called anethole, which is used to give flavour to liquors like Galliano, Ouzo, sambuca and absinthe. Much like myself, it loves alcohol. Its hydrophobic nature means it can’t be dissolved in water unless it’s first dissolved in alcohol. But when you add water, it creates a microemulsion (a mixture of two liquids that don’t want to mix, like oil and water). The resulting beverage is milky white, which you’ll be familiar with if you’ve ever added water to Ouzo.

If the thought of flaming sambuca shots makes your mouth water, don’t worry, you don’t need to get into a 12-step program. A drug commonly used to treat the dry mouth that patients experience while undergoing chemotherapy is derived from anethole.

So, back to the flu.
The other chemical compound that star anise is rife with is shikimic acid. It’s a very important compound that’s a precursor for a lot of other important biological compounds in nature; it’s an important building block. And it’s a huge building block for the drug company Roche, as the main ingredient in their anti-flu drug Tamiflu.

It’s so important to Tamiflu production that 90% of the Chinese star anise harvest goes to Roche, and that any shortage in star anise can actually cause a bottleneck in production. This was the case in the flu outbreaks in 2005 and 2009 as the world scrambled to stockpile doses (anyone remember swine flu?), and the price of star anise skyrocketed. It takes 13 g of star anise to make 1.3 g of shikimic acid, which can be turned into 10 Tamiflu capsules.

As a result of the worldwide shortages and panic over not having enough Tamiflu doses, scientists have uncovered a few alternative ways to extract shikimic acid from bacteria or pine needles. Necessity is the mother of invention, but the most efficient way is still to get it from star anise.

So there you have it!
I knew that mysterious little pod would have some delightful secrets to share, and it just so happens that they involve two of my favourite things: booze and drugs.

Seeking SciNote, Chemistry: Flavorings

Question:

What are artificial flavorings? 

Asked by Anonymous 

Answer:

There are many different terms used in the flavor industry (which is big business nowadays) and it can get confusing. The terms “artificial flavors,” “natural flavors,” “flavor additives,” and “flavor enhancers,” among others have had their official definitions change over the years and different countries may employ different definitions.

Natural flavors are essentially flavoring agents (i.e. chemicals) that can be found in nature. According to the U.S. Food and Drug Administration (FDA), a natural flavor means “the essential oil, oleoresin, essence or extractive, protein hydrolysate, distillate, or any product of roasting, heating or enzymolysis, which contains the flavoring constituents derived from a spice, fruit or fruit juice, vegetable or vegetable juice, edible yeast, herb, bark, bud, root, leaf or similar plant material, meat, seafood, poultry, eggs, dairy products, or fermentation products thereof, whose significant function in food is flavoring rather than nutritional.”

This definition can be found the Code of Federal Regulations where the definition of artificial flavoring can also be found – “any substance, the function of which is to impart flavor, which is not derived from a spice, fruit or fruit juice, vegetable or vegetable juice, edible yeast, herb, bark, bud, root, leaf or similar plant material, meat, fish, poultry, eggs, dairy products, or fermentation products thereof.” Essentially this means that an artificial flavor is a synthetic, or man-made, chemical (or usually a mix of chemicals).

Regardless of whether they are natural or not, flavorings are chemicals, and usually natural and artificial flavorings are actually the same chemicals – the difference is simply how they are obtained. Flavor chemists, sometimes dubbed “flavorists,” can either extract the chemicals from a naturally occurring item (like a piece of fruit), or they can synthesize the chemicals from other starting materials, but ultimately the chemical or chemicals used in the flavoring are the same (Longo).

The actual chemicals used in the flavoring of different foods is difficult to say; the formulas and/or mixture combinations are often trade secrets. Flavor companies like Givaudan, Cargill, Takasago, and International Flavors & Fragrances (IFF) guard these formulations well. Many of them involve compounds like esters, which are chemical compounds that are derived from carboxylic acids. Esters tend to have pleasant odors. and our sense of smell is closely linked to our sense of taste. To get more specific than that would require a chemical analysis. Eric Schlosser in his seminal book “Fast Food Nation” described a typical artificial strawberry flavor (like in a Burger King milk shake) to have the following ingredients: “amyl acetate, amyl butyrate, amyl valerate, anethol, anisyl formate, benzyl acetate, benzyl isobutyrate, butyric acid, cinnamyl isobutyrate, cinnamyl valerate, cognac essential oil, diacetyl, dipropyl ketone, ethyl acetate, ethyl amylketone, ethyl butyrate, ethyl cinnamate, ethyl heptanoate, ethyl heptylate, ethyl lactate, ethyl methylphenylglycidate, ethyl nitrate, ethyl propionate, ethyl valerate, heliotropin, hydroxyphenyl-2-butanone (10 percent solution in alcohol), α-ionone, isobutyl anthranilate, isobutyl butyrate, lemon essential oil, maltol, 4-methylacetophenone, methyl anthranilate, methyl benzoate, methyl cinnamate, methyl heptine carbonate, methyl naphthyl ketone, methyl salicylate, mint essential oil, neroli essential oil, nerolin, neryl isobutyrate, orris butter, phenethyl alcohol, rose, rum ether, γ-undecalactone, vanillin, and solvent.”

Most of the flavor and smell comes from just one or two of these chemicals, but a list like that can be overwhelming. Many people are concerned with all of these substances being in their foods. The FDA recognizes that foods themselves are just mixtures of chemicals, though, and they do at least limit the chemicals allowed in our food and the quantities of these chemicals to levels Generally Regarded As Safe (GRAS). This may not sound reassuring, but whether a compound is GRAS and at what levels is usually determined by careful study of the compound structure, its human use history (if it has any), and its processing technique (i.e. how much solvent remains from the production or extraction and whether there are any significant contaminants or side products from production).

Answered by Brian C., Expert Leader

References
“CFR - Code of Federal Regulations Title 21.” CFR - Code of Federal Regulations Title 21. Food and Drug
Administration, n.d. Web. 27 Jan. 2015.

Natasha, Longo. “Food Labs Use An Average of 2000 Chemicals To Create 500 ‘Natural Flavors’ You
Would Never Suspect Are Artificial.” Food Labs Use An Average of 2000 Chemicals To Create 500
'Natural Flavors’ You Would Never Suspect Are Artificial. N.p., 26 Aug. 2013. Web. 27 Jan. 2015.

Schlosser, Eric. “Why the Fries Take So Good.” Fast Food Nation: The Dark Side of the All-American Meal.
Boston: Houghton Mifflin, 2001. 125-26. Print.