Org Prep Daily

October 18, 2011

Trehalose!

Filed under: lit highlights — milkshake @ 12:07 am

A remarkable molecule:  Hygroscopic, edible, stable and pleasantly-tasting natural sugar. While keeping foodstuff moist and producing a desirable mouth-feel, trehalose also masks greasy rancid off-flavors like no other food additive. Trehalose inhibits lipid autooxidation by interacting with the C=C bonds of fatty acids. Trehalose has also a stabilizing effect on denaturation-prone proteins. It is an effective cryoprotectant and anti-desiccant for living cells.

Trehalose is widely used as food additive in Japan. (It got classified by FDA recently as ‘generally recognized safe’  so expect trehalose-immortalized pastry snacks at gas stations soon). Two protein-based drugs co-formulated with trehalose are already on the market.

I would like to direct you to a minireview from Dr. Higashiama, a research team leader at the trehalose manufacturer Hayashibara Co. Some important practical applications are discussed in detail:

“In this application, we examined the suppressive effect of trehalose on human body odor. The typical odor of a senior layer (odor from seniors) increases with age, especially 55 years or older. This odor contains unsaturated aldehydes such as 2-nonenal and 2-octenal. These aldehydes are produced by the degradation of unsaturated fatty acid (palmitoleic acid) in aged people’s skin. The subjects (55 years or older) were selected from our company. After a shower, their body was sprayed with a 2 % trehalose solution. They put on new underwear after the spray. Twenty hours later, the unsaturated aldehydes were sampled from the used underwear shown in this system using DNPH-column. The trapped aldehydes were eluted from this column and were analyzed by gas chromatography. The results showed a decrease of about 70 % in odor from seniors due to the action of trehalose (Fig. 7). This result indicates that trehalose has a suppressive effect on the formation of the odor released by the seniors’ bodies. The same results came out with the oxidation of fatty acid. Therefore, the application of trehalose for cosmetic fields is expected.”

T. Higashiama: Pure and Applied Chemistry 74, 1263–1269

(Fig. 8):

October 4, 2011

A scent of fresh soil

Filed under: Uncategorized — milkshake @ 5:53 pm

Our lab has been smelling a lot like disturbed soil lately, due to my work with 2-ethylfenchol. The flavor and fragrance division of Aldrich is a good place to start when you need highly hindered tertiary alcohols. While many of the low-molecular weight tertiary alcohols are minty and camphor-like, Et-fenchol smells like dirt. Actually in the concentrated state it reeks similar to TBS-silanol, but stronger. In more diluted form though it has a clean smell of freshly dug-up moist earth –  the smell is persistant and very convincing; a colleague asked me if he could wear ethylfenchol on his shroud when he goes to a Halloween party dressed as a mummy.

Turns out, 2-ethylfenchol prepared from (+)-enantiomer of fenchone has been developed with a specific purpose: as a substitute for geosmin – the terpenoid metabolite produced by soil bacteria that makes soil smell earthy. The earthy note is desirable in some compositions, i.e. for pipe tobacco flavoring, and since geosmin is rather hard to make cheaply a semisynthetic substitute was found. (Water utility companies are less fond of geosmin; the odor threshold of geosmin is incredibly low. Together with 2-methylisoborneol – another dirty-smelling terpenoid from soil bacteria/fungi – geosmin lends awful taste to tap water).

Et-fenchol from Aldrich comes in kosher grade, with a large seal from rabbi Gershon Segal on the bottle:

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