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ASPARAGUS AND THE SMELL
Asparagusic acid is the organosulfur with the formula S2(CH2)2CHCO2H. The molecule contains both carboxylic acid and disulfide functional groups. It is present in the vegetable asparagus and may be the metabolic precursor to other odorous thiol compounds.
The material was originally isolated from an aqueous extract of asparagus.
Biosynthetic studies revealed that asparagusic acid is derived from isobutyric acid. This colorless solid has a melting point (m.p.) of 75.7–76.5 °C. The corresponding dithiol (m.p. 59.5–60.5 °C) is also known; it is called dihydroasparagusic acid or dimercaptoisobutyric acid.
Over the past forty years several papers have been published on the subject, and several studies undertaken, to try and determine the chemical compounds responsible, and though there is still no definitive verdict as to the manner in which these compounds are formed, it has been suggested that they all form from asparagusic acid.
Asparagusic acid is, unsurprisingly considering the name, a chemical found exclusively in asparagus, and absent in other related vegetables.
The asparagus-pee molecules that you smell come mostly from the breakdown of a molecule known as asparagusic acid, which is present naturally in asparagus. When your body breaks down asparagusic acid it forms a wide variety of chemicals, all of which contain sulfur!
This has made it an obvious candidate for being the origin of the peculiar effect that asparagus has on urine. It has been suggested by recent studies that it could be metabolised in the body to produce the volatile compounds found in the urine after consuming the vegetable.
Steamed asparagus prepared with roasted pine nuts
Many chemicals that contain sulfur atoms smell horrible in similar ways, and I have no idea why this is. This is one chemical/biological mystery that, much to my chagrin, remains unsolved in my head (internet people, if the reason is known, please help!).
Aside from sulfur, the thing that all these smelly asparagus-pee chemicals have in common is that they are “light” enough (a.k.a. they are “volatile”, which means they have a relatively low boiling point) that they can float up into the air and into your nose. That is partly why asparagus doesn’t smell like asparagus-pee, because asparagusic acid is not volatile (remember that word). In fact, asparagusic acid boils above 300 °C (>600 °F), so there is no way any of it gets into your nose!
Asparagus has been used as a vegetable and medicine, owing to its delicate flavour, diuretic properties, and more. It is pictured as an offering on an Egyptian frieze dating to 3000 BC. Still in ancient times, it was known in Syria and in Spain. Greeks and Romans ate it fresh when in season and dried the vegetable for use in winter; Romans would even freeze it high in the Alps, for the Feast of Epicurus. Emperor Augustus tossed off the “Asparagus Fleet” for hauling the vegetable, and coined the expression “faster than cooking asparagus” for quick action. A recipefor cooking asparagus is in the oldest surviving book of recipes, Apicius’s third-century AD De re coquinaria, Book III.
The ancient Greek physician Galen (prominent among the Romans) mentioned asparagus as a beneficial herb during the second century AD, but after the Roman empire ended, asparagus drew little medieval attention. until al-Nafzawi‘s The Perfumed Garden. That piece of writing celebrates its (scientifically unconfirmed) aphrodisiacal power, a supposed virtue that the IndianAnanga Ranga attributes to “special phosphorus elements” that also counteract fatigue. By 1469, asparagus was cultivated in French monasteries. Asparagus appears to have been hardly noticed in England until 1538, and in Germany until 1542.
The finest texture and the strongest and yet most delicate taste is in the tips. The points d’amour (“love tips”) were served as a delicacy to Madame de Pompadour. Asparagus became available to the New World around 1850, in the United States.
Certain compounds in asparagus are metabolized to yield ammonia and various sulfur-containing degradation products, including various thiols andthioesters, which give urine a characteristic smell.
Some of the volatile organic compounds responsible for the smell are:
- dimethyl sulfide
- dimethyl disulfide
- dimethyl sulfoxide
- dimethyl sulfone
Subjectively, the first two are the most pungent, while the last two (sulfur-oxidized) give a sweet aroma. A mixture of these compounds form a “reconstituted asparagus urine” odor. This was first investigated in 1891 by Marceli Nencki, who attributed the smell to methanethiol. These compounds originate in the asparagus as asparagusic acid and its derivatives, as these are the only sulfur-containing compounds unique to asparagus. As these are more present in young asparagus, this accords with the observation that the smell is more pronounced after eating young asparagus. The biological mechanism for the production of these compounds is less clear.
The onset of the asparagus urine smell is remarkably rapid. The smell has been reported to be detectable 15 to 30 minutes after ingestion.
Gas chromatography-mass spectrometry was used to analyse the ‘headspace’ of urine produced after consumption of asparagus. The headspace is the gas space immediately above the liquid surface, which is occupied by light, volatile compounds in the liquid, and analysis of this is useful in identifying odour-causing compounds. The analysis of the post-asparagus urine showed the presence of several compounds that were not present, or present in negligible amounts, in normal urine. The primary compounds present, in quantities a thousand times greater than in normal urine, were methanethiol and dimethyl sulfide. The compounds dimethyl sulfide and dimethyl sulfone were also present and it was suggested that they modify the aroma to give it a ‘sweet’ edge.
|Nutritional value per 100 g (3.5 oz)|
|Energy||85 kJ (20 kcal)|
|– Sugars||1.88 g|
|– Dietary fibre||2.1 g|
|Vitamin A equiv.||38 μg (5%)|
|– beta-carotene||449 μg (4%)|
|– lutein and zeaxanthin||710 μg|
|Thiamine (vit. B1)||0.143 mg (12%)|
|Riboflavin (vit. B2)||0.141 mg (12%)|
|Niacin (vit. B3)||0.978 mg (7%)|
|Pantothenic acid (B5)||0.274 mg (5%)|
|Vitamin B6||0.091 mg (7%)|
|Folate (vit. B9)||52 μg (13%)|
|Choline||16 mg (3%)|
|Vitamin C||5.6 mg (7%)|
|Vitamin E||1.1 mg (7%)|
|Vitamin K||41.6 μg (40%)|
|Calcium||24 mg (2%)|
|Iron||2.14 mg (16%)|
|Magnesium||14 mg (4%)|
|Manganese||0.158 mg (8%)|
|Phosphorus||52 mg (7%)|
|Potassium||202 mg (4%)|
|Sodium||2 mg (0%)|
|Zinc||0.54 mg (6%)|
Link to USDA Database entry
Greek Herbs- Fennel (saunf)
History of Fennel
Ancient Greeks and Indian cultures used fennel for cooking and as part of traditional herbal medicine. The Greeks and Indians traditionally combined fennel with other herbs to make home remedies for the relief of gastrointestinal problems such as acidity and indigestion.
The essential oil of fennel contains approximately 5 percent limonene, 50 to 80 percent anethole and 5 percent fenchone. Additionally, the oil contains trace amounts of a-pinene, estragole, b-pinene, safrole, b-myrcene, camphene and p-cymene. The seeds from the fennel plant also contain fiber and complex carbohydrates. Fennel contains nutrients including vitamin B-3, magnesium, molybdenum, copper, phosphorus, iron, calcium, manganese, vitamin C, folate and potassium.
As a health supplement, fennel can help to prevent gas, support digestion and function as an expectorant that can help to relieve minor respiratory problems such as mucus. Fennel also contains anti-inflammatory properties when used externally. The leaves from the fennel plant can facilitate the healing of wounds and burns. The root of the fennel plant is diuretic and can help treat urine infections. Fennel also contains a combination of phytonutrients including the flavonoids rutin, quercitin and kaempferol. Fennel also has antioxidant properties and as a dietary fiber, it can help lower your cholesterol levels.
Health supplement manufacturers offer fennel supplements in powdered form. As a supplement, manufacturers recommend taking 1 to 4 g per day of the powdered fennel supplement. The Food and Drug Administration, however, has not established a recommended dose for fennel powder. There are no known side effects of consuming fennel powder supplements, although you should speak with your doctor prior to using fennel powder if you are attempting to treat a specific medical condition.
The bulb, foliage, and seeds of the fennel plant are widely used in many of the culinary traditions of the world. The small flowers of wild fennel (mistakenly known in America as fennel “pollen” ) are the most potent form of fennel, but also the most expensive.Dried fennel seed is an aromatic, anise-flavoured spice, brown or green in colour when fresh, slowly turning a dull grey as the seed ages. For cooking, green seeds are optimal. The leaves are delicately flavoured and similar in shape to those of dill. The bulb is a crisp vegetable that can be sautéed, stewed, braised, grilled, or eaten raw. They are used for garnishes and to add flavor to salads. They are also added to sauces and served with pudding. The leaves used in soups and fish sauce and sometimes eaten raw as salad.
Fennel seeds are sometimes confused with those of anise, which are similar in taste and appearance, though smaller. Fennel is also used as a flavouring in some natural toothpastes. The seeds are used in cookery and sweet desserts.
Many cultures in India, Pakistan, Afghanistan, Iran and the Middle East use fennel seed in their cookery. It is one of the most important spices in Kashmiri Pandit and Gujarati cooking. It is an essential ingredient of the Assamese/Bengali/Oriya spice mixture panch phoron and in Chinese five-spice powders. In many parts of India and Pakistan, roasted fennel seeds are consumed as mukhwas, an after-meal digestive and breath freshener. Fennel leaves are used as leafy green vegetables either by themselves or mixed with other vegetables, cooked to be served and consumed as part of a meal, in some parts of India. In Syria and Lebanon, it is used to make a special kind of egg omelette (along with onions, and flour) called ijjeh.
Many egg, fish, and other dishes employ fresh or dried fennel leaves. Florence fennel is a key ingredient in some Italian and German salads, often tossed with chicory and avocado, or it can be braised and served as a warm side dish. It may be blanched or marinated, or cooked in risotto.
In Spain the stems of the fennel plant are used in the preparation of pickled eggplants, “berenjenas de Almagro”.
Fennel contains anethole, which can explain some of its medical effects: It, or its polymers, act as phytoestrogens.
The essence of fennel can be used as a safe and effective herbal drug for primary dysmenorrhea, but could have lower potency than mefenamic acid at the current study level.
Fennel is widely employed as a carminative, both in humans and in veterinary medicine (e.g., dogs), to treat flatulence by encouraging the expulsion of intestinal gas. Anethole is responsible for the carminative action.
Mrs. Eencher Herbal states:
On account of its carminative properties, fennel is chiefly used medicinally with purgatives to allay their side effects, and for this purpose forms one of the ingredients of the well-known compound liquorice powder. Fennel water has properties similar to those of anise and dill water: mixed with sodium bicarbonate and syrup, these waters constitute the domestic ‘gripe water‘ used to correct the flatulence of infants. Volatile oil of fennel has these properties in concentration. Commercial preparations of fennel are widely available as alternative treatment for baby colic. Fennel tea, also employed as a carminative, is made by pouring boiling water on a teaspoonful of bruised fennel seeds.
Fennel can be made into a syrup to treat babies with colic (formerly thought to be due to digestive upset), but long-term ingestion of fennel preparations by babies is a known cause of thelarche.
In the Indian subcontinent, fennel seeds are also eaten raw, sometimes with some sweetener, as they are said to improve eyesight. Ancient Romans regarded fennel as the herb of sight.Root extracts were often used in tonics to clear cloudy eyes. Extracts of fennel seed have been shown in animal studies to have a potential use in the treatment of glaucoma.
Blood and urine
Fennel may be an effective diuretic and a potential drug for treatment of hypertension.
There are historical anecdotes that fennel is a galactagogue,improving the milk supply of a breastfeeding mother. This use, although not supported by direct evidence, is sometimes justified by the fact that fennel is a source of phytoestrogens, which promote growth of breast tissue. However, normal lactation does not involve growth of breast tissue. A single case report of fennel tea ingested by a breastfeeding mother resulted in neurotoxicity for the newborn child.
Syrup prepared from fennel juice was formerly given for chronic coughs. It is one of the plants which is said to be disliked by fleas, and powdered fennel has the effect of driving away fleas from kennels and stables.
- “Herbs That Work: The Scientific Evidence of Their Healing Powers”; David Armstrong
- “The Encyclopedia of Herbs: A Comprehensive Reference to Herbs of Flavor and Fragrance”; Arthur O. Tucker and Thomas DeBaggio; 2009
- “Pocket Guide to Herbal Remedies”; Lane P. Johnson; 2002
- “Encyclopedia of Natural Medicine”; Michael Murray and Joseph Pizzorno; 1997