March is the season of the March hare, the Mad Hatter, and
the Academy Awards.
the Academy Awards.
Asparagus is in season. We put the pot on to boil as Matthew McConaughey and
his mom strolled the red carpet.
We were munching the savory stocks as Pink sang “Over the Rainbow,”
and by the time Steve McQueen defied Gravity with his serious jumps,
an acrid aroma wafted from the white throne in the ground-floor bathroom.
his mom strolled the red carpet.
We were munching the savory stocks as Pink sang “Over the Rainbow,”
and by the time Steve McQueen defied Gravity with his serious jumps,
an acrid aroma wafted from the white throne in the ground-floor bathroom.
What is it about asparagus and stinky pee?
Where to begin? Queen Anne’s physician, John Arlbuthnot, called it “a foetid smell” in 1731. Fifty years later, Benjamin Franklin was more reserved, calling it an “disagreeable odor.” Polish scientist Marceli Nencki was the first to apply science to the stink. He identified a compound called methanethiol as the cause in 1891. Research reved up when disco, and the mosh pits of punk rock hit the scene. Asparagus, sweaty dancing. You get the picture.
When an asparagus stalk falls and nobody is there to smell it, does it still stink?
22-50% of the population reports strange smelling pee from asparagus.
This is 2014 and DNA is the big story
in everything from hair color to where God lives.
in everything from hair color to where God lives.
Erica Chan (2013) defines two distinct DNA camps. One camp proposes that some of us lack the DNA to break asparagus down into it’s sulfurous components. The other camp feels that some of us simply cannot smell sulfur because we lack some sort of olfactory DNA. Scientific evidence weighs in on both sides.
Some pee just doesn’t stink. Waring et al. (1987) found that some people who ate asparagus did not produce stinky urine; others did. Using gas chromatography, they found five sulfur compounds in the stinky urine, and none in the non-stinky urine.
Some noses don’t get it. Lison et al. (1980) found that some people can smell asparagus in the urine, and others cannot. They used a clever device in their research - they created varying degrees of dilution, and found a variation in the ability of “smellers” to detect the odor. Then, they took it a step further and had all 328 of their subjects eat asparagus. Every one of them had the stink. Not all of them could smell it. So, they concluded that if an asparagus stalk falls in the woods and there is nobody there to smell it, it will still smell.
What, exactly, is that smell?
Yes, it smells. But, you say, it does not smell like sulfur. I agree. The odor has a metallic ring to it, something like the vapor that wafts from a newly opened bottle of B
vitamins.
vitamins.
To be sure, asparagus does contain sulfur. The formula for asparagusic acid is S2(CH2)2CHCO2H. ( Dear Mr. Lindsey, my 11th grade science teacher, I know the “2” should be in subscript but I lack the typographic skills.)
The urine smell, however, comes from the way our bodies digest and metabolize asparagus. Cecil Adams (1985) opined that the smell comes from metabolized thioesters. Like several other writers, Adams cites Robert H. White (1975), a chemist at the University of California at San Diego, who used gas chromatography to pin down several compounds known as
S-Methyl Thioesters as the culprits.
S-Methyl Thioesters as the culprits.
In our tummies, the sulfur in asparagusic acid displaces hydroxy molecules in alcohol to become thiol. For English speaking readers, we will break this down later. If you’re sober and wondering how alcohol got into your belly, then simply recall that all sugars take on hydroxy molecules while digesting, which is very similar to
fermentation. Thiols have strong odors resembling garlic. One form is used to scent bottled gas so we can know if our BBQ gas is leaking.
fermentation. Thiols have strong odors resembling garlic. One form is used to scent bottled gas so we can know if our BBQ gas is leaking.
Chemistry 101: Molecules & stinky pee
Our stomach acid combines with thiols to form S-methyl thioesters, specifically S-methyl thioacrylate and S-methyl 3-(methylthio)thiopropionate.
That’s what you’re smelling when you pee after asparagus.
That’s what you’re smelling when you pee after asparagus.
The thioacrylate recipe is: CH2=CHC(=O)SCH3
The thiopropionate is: CH3SCH2CH2C(=O)SCH3
Let’s break this down.
1. Asparagus contains asparagusic acid.
2. During digestion, asparagusic acid breaks down into thiols.
2.1 Thiols are a portmanteau of the Greek thion (sulfur) + alcohol.
2.2 Thiols happen when sulfur replaces the hydroxy (OH) molecule in alcohol
3. Thiols combine with stomach acids to form thioesters
3.2 Esterification means two reactants (here, an alcohol and an acid) form an ester as the reaction product.
3.3 Esters often have a characteristic pleasant, fruity odor. This leads to their
use in the fragrance and flavor industry, which is why your raspberry flavor comes from
beaver glands...but I digress.
use in the fragrance and flavor industry, which is why your raspberry flavor comes from
beaver glands...but I digress.
Why is asparagus good for you?
For one thing, (2.2) it changes alcohol into stinky pee. That’s an easier burden to bear than a DUI arrest. It could come in handy on St. Patrick’s Day.
For another, thions are known as “mercaptans” from the Latin mercurium captans (capturing mercury.) So, digested asparagus may free mercury and send it into the toilet in a safe, bound form, rather than as a nerve-shattering agent that can make you a Mad Hatter.
References:
Adams, Cecil, The Straight Dope (August 30, 1985)
Chan, Erica, Daily Californian (APRIL 17, 2013)
Lison, M., S. H. Blondheim, and R. N. Melmed. 1980. A polymorphism of the ability to smell urinary metabolites of asparagus. British Medical Journal 281: 1676-1678.
Waring, R. H., S. C. Mitchell, and G. R. Fenwick. 1987. The chemical nature of the urinary odour produced by man after asparagus ingestion. Xenobiotica 17:1363-1371.
White, Robert H. (1975), a chemist at the University of California at San Diego, None of the article writers can state a specific citation, nor can I. So, you’ll just have to take our word for it.