Names | |
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Preferred IUPAC name 3-Hydroxy-4,5-dimethylfuran-2(5H)-one | |
Other names Sotolone Caramel furanone Sugar lactone Fenugreek lactone | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.044.655 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H8O3 | |
Molar mass | 128.127 g·mol−1 |
Density | 1.049 g/cm3 |
Melting point | 26 to 29 °C (79 to 84 °F; 299 to 302 K) |
Boiling point | 184 °C (363 °F; 457 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. Sotolon is the major aroma and flavor component of fenugreek seed and lovage, [1] and is one of several aromatic and flavor components of artificial maple syrup. [2] It is also present in molasses, aged rum, aged sake and white wine, flor sherry, roast tobacco, [3] and dried fruiting bodies of the mushroom Lactarius helvus . [4] Sotolon can pass through the body relatively unchanged, and consumption of foods high in sotolon, such as fenugreek, can impart a maple syrup aroma to one's sweat and urine. In some individuals with the genetic disorder maple syrup urine disease, it is spontaneously produced in their bodies and excreted in their urine, leading to the disease's characteristic smell. [5]
This molecule is thought to be responsible for the mysterious maple syrup smell that has occasionally wafted over Manhattan since 2005. [6] Sotolon was first isolated in 1975 from the herb fenugreek. [7] The compound was named in 1980 when it was found to be responsible for the flavor of raw cane sugar: soto- means "raw sugar" in Japanese and -olon signifies that the molecule is an enol lactone. [8]
Several aging-derived compounds have been pointed out as playing an important role on the aroma of fortified wines; however, sotolon (3-hydroxy-4,5-dimethyl-2(5H)-furanone) is recognized as being the key odorant and has also been classified as a potential aging marker of these type of wines. This chiral lactone is a powerful odorant, which can impart a nutty, caramel, curry, or rancid odor, depending on its concentration and enantiomeric distribution. Despite being pointed out as a key odorant of other fortified wines, the researchers’ attention has also been directed to its off-flavor character, associated to the premature oxidative aging of young dry white wines, overlapping the expected fruity, flowery, and fresh character. This compound can be detected by miniaturized emulsification extraction followed by GC–MS/SIM [9] and single-step miniaturized liquid-liquid extraction followed by LC-MS/MS analysis [10]
Vin jaune is marked by the formation of sotolon from α-ketobutyric acid. [11] [12]
Maple syrup is a syrup made from the sap of maple trees. In cold climates, these trees store starch in their trunks and roots before winter; the starch is then converted to sugar that rises in the sap in late winter and early spring. Maple trees are tapped by drilling holes into their trunks and collecting the sap, which is processed by heating to evaporate much of the water, leaving the concentrated syrup.
Fenugreek is an annual plant in the family Fabaceae, with leaves consisting of three small obovate to oblong leaflets. It is cultivated worldwide as a semiarid crop. Its seeds and leaves are common ingredients in dishes from the Indian subcontinent, and have been used as a culinary ingredient since ancient times. Its use as a food ingredient in small quantities is safe.
Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely used, but naturally forms in low quantities in many types of fermented foods and drinks.
An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.
cis-3-Hexen-1-ol, also known as (Z)-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. cis-3-Hexen-1-ol is a very important aroma compound that is used in fruit and vegetable flavors and in perfumes. The yearly production is about 30 tonnes.
Maple syrup urine disease (MSUD) is an autosomal recessive metabolic disorder affecting branched-chain amino acids. It is one type of organic acidemia. The condition gets its name from the distinctive sweet odor of affected infants' urine and earwax, particularly prior to diagnosis and during times of acute illness. It was described by John Menkes in the 1950s.
The odor detection threshold is the lowest concentration of a certain odor compound that is perceivable by the human sense of smell. The threshold of a chemical compound is determined in part by its shape, polarity, partial charges, and molecular mass. The olfactory mechanisms responsible for a compound's different detection threshold is not well understood. As such, odor thresholds cannot be accurately predicted. Rather, they must be measured through extensive tests using human subjects in laboratory settings.
Frutarom Industries Ltd. is an Israeli-based company that specializes in the production and distribution of extracts for flavor and fragrance. In 2015 it had sales of over $872 million.
Candy cap or curry milkcap is the English-language common name for two closely related edible species of Lactarius; L. camphoratus, and L. rubidus. These mushrooms are valued for their highly aromatic qualities and are used culinarily as a flavoring rather than as a constituent of a full meal.
α-Ketobutyric acid is an organic compound with the formula CH3CH2C(O)CO2H. It is a colorless solid that melts just above room temperature. Its conjugate base α-ketobutyrate is the predominant form found in nature (near neutral pH). It results from the lysis of cystathionine. It is also one of the degradation products of threonine, produced by the catabolism of the amino acid by threonine dehydratase. It is also produced by the degradation of homocysteine and the metabolism of methionine.
The use of wine tasting descriptors allows the taster to qualitatively relate the aromas and flavors that the taster experiences and can be used in assessing the overall quality of wine. Wine writers differentiate wine tasters from casual enthusiasts; tasters attempt to give an objective description of the wine's taste, casual enthusiasts appreciate wine but pause their examination sooner than tasters. The primary source of a person's ability to taste wine is derived from their olfactory senses. A taster's own personal experiences play a significant role in conceptualizing what they are tasting and attaching a description to that perception. The individual nature of tasting means that descriptors may be perceived differently among various tasters.
3-Mercapto-3-methylbutan-1-ol, also known as MMB, is a common odorant found in food and cat urine. The aromas ascribed to MMB include catty, roasty, broth-like, meaty, and savory, or similar to cooked leeks.
Lactarius helvus, commonly known as fenugreek milkcap, is a member of the large milkcap genus Lactarius in the order Russulales. Fruiting bodies can be found in Sphagnum moss in coniferous and deciduous woodland in Europe, and possibly North America, although considerable debate continues about the North American variety, formerly referred to as Lactarius aquifluus. Mushrooms are pale brown-grey or beige in colour and funnel-shaped, with colourless, watery milk. Its distinctive smell has been likened to fenugreek, celery, liquorice, or Maggi instant soup. Mildly toxic when raw, it has been implicated in the poisoning of 418 people near Leipzig in October 1949. However, it is used in small quantities as a spice when dried. Sotolon, the agent that gives the fungus its odour, also occurs in fenugreek, maple syrup and lovage.
Food pairing is a method of identifying which foods go well together from a flavor standpoint, often based on individual tastes, popularity, availability of ingredients, and traditional cultural practices.
The aromas of wine are more diverse than its flavours. The human tongue is limited to the primary tastes perceived by taste receptors on the tongue – sourness, bitterness, saltiness, sweetness and savouriness. The wide array of fruit, earthy, leathery, floral, herbal, mineral, and woodsy flavour present in wine are derived from aroma notes sensed by the olfactory bulb. In wine tasting, wine is sometimes smelled before taking a sip in order to identify some components of the wine that may be present. Different terms are used to describe what is being smelled. The most basic term is aroma which generally refers to a "pleasant" smell as opposed to odour which refers to an unpleasant smell or possible wine fault. The term aroma may be further distinguished from bouquet which generally refers to the smells that arise from the chemical reactions of fermentation and aging of the wine.
Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar content, acidity and the presence of secondary compounds. Vines store sugar in grapes through photosynthesis, and acids break down as grapes ripen. Secondary compounds are also stored in the course of the season. Anthocyanins give grapes a red color and protection against ultraviolet light. Tannins add bitterness and astringency which acts to defend vines against pests and grazing animals.
Coffee furanone (2-methyltetrahydrofuran-3-one) is a pleasant smelling liquid furan derivative which is a volatile constituent of the aroma complex of roasted coffee. Coffee furanone is less odorous than furfuryl mercaptan, which with an odor threshold of 0.005 ppb was the first high impact aroma chemical, but has a very pleasant sweet caramel character, with some nuttiness.
2-Hydroxy-3-methyl-2-cyclopenten-1-one is an organic compound related to 1,2-cyclopentanedione. It is the enol tautomer of the diketone 3-methylcyclopentane-1,2-dione. Being an enol, the compound is often called methylcyclopentenolone. It is a colorless solid.
Zygosaccharomyces rouxii is a species of yeast in the genus Zygosaccharomyces. Initially described as Saccharomyces rouxii by Boutroux in 1883, it was then moved to the genus Zygosaccharomyces in the work of Barnett et al. It is remarkably tolerant of high concentrations of sugar or salt, making it a spoilage agent of otherwise stable foods, but also present in fermentation of products such as soy sauce or balsamic vinegar.
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