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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 412326577
| Watchedfields = changed
⚫ | verifiedrevid = 430052899
| ImageFile = Sotolon_chemical_structure.png | ImageFile = Sotolon_chemical_structure.png
| ImageSize = | ImageSize = 160
| ImageFile1 = Sotolon 3D ball.png
⚫ | IUPACName = 3-Hydroxy-4,5-dimethylfuran-2(''5H'')-one
| ImageSize1 = 160
⚫ | OtherNames = Sotolone<br>Caramel furanone<br>Sugar lactone<br>Fenugreek lactone
| ImageAlt1 = Ball-and-stick model of the sotolon molecule
⚫ | Section1 = {{Chembox Identifiers
⚫ | PIN = 3-Hydroxy-4,5-dimethylfuran-2(''5H'')-one
⚫ | CASNo = 28664-35-9
⚫ | OtherNames = Sotolone<br/>Caramel furanone<br/>Sugar lactone<br/>Fenugreek lactone
⚫ | PubChem = 5325921
⚫ |Section1={{Chembox Identifiers
⚫ | SMILES = O=C1OC(C)C(C)=C1O
| CASNo_Ref = {{cascite|correct|??}}
⚫ | CASNo = 28664-35-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = T62RL2NEGW
⚫ | SMILES = O=C1OC(C)C(C)=C1O
⚫ | PubChem = 62835
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 56569
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UNYNVICDCJHOPO-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6|H=8|O=3
| Formula = C<sub>6</sub>H<sub>8</sub>O<sub>3</sub>
⚫ | Appearance =
| MolarMass = 128.13 g/mol
⚫ | Density = 1.049 g/cm<sup>3</sup>
⚫ | Appearance =
| MeltingPtC = 26 to 29
⚫ | Density = 1.049 g/cm<sup>3</sup>
| MeltingPt = | BoilingPtC = 184
⚫ | Solubility =
| BoilingPtC = 184
⚫ | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}


'''Sotolon''' (also known as '''sotolone''') is a ] and an extremely powerful ], with the typical smell of ] or ] at high concentrations and ], ], or burnt sugar at lower concentrations. Sotolon is the major aroma and flavor component of fenugreek seed and ],<ref>{{cite journal | author =Imre Blank, Peter Schieberle | title =Analysis of the seasoning-like flavour substances of a commercial lovage extract | journal =Flavour and Fragrance Journal | year =1993 | volume =8 | issue = | pages =191–195 | doi =10.1002/ffj.2730080405 | url =http://www3.interscience.wiley.com/cgi-bin/abstract/112664676/ABSTRACT | format =abstract}}</ref> and is one of several aromatic and flavor components of ].<ref></ref> It is also present in ], aged ], aged sake and white wine, ] ], roast tobacco,<ref></ref> and dried fruiting bodies of the mushroom '']''.<ref>{{cite journal | author =Sylvie Rapior, Françoise Fons and Jean-Marie Bessièreb | title =The fenugreek odor of Lactarius helvus | journal = Mycologia | year = 2000| volume =92 | issue =2 | pages =305–308 | doi = 10.2307/3761565| url =http://apt.allenpress.com/aptonline/?request=get-abstract&issn=0027-5514&volume=092&issue=02&page=0305 | format =abstract | jstor =3761565 | publisher =Mycological Society of America}}</ref> 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 ], it is spontaneously produced in their bodies and excreted it in their urine, leading to the disease's characteristic smell.<ref>{{cite journal | author =F. Podebrad, M. Heil, S. Reichert1, A. Mosandl, A. C. Sewell and H. Böhles | title =4,5-Dimethyl-3-hydroxy-2-furanone (sotolone) — The odour of maple syrup urine disease | journal =Journal of Inherited Metabolic Disease | year =1999 | volume =22 | issue =2 | pages =107–114 | doi =10.1023/A:1005433516026 | url =http://www.springerlink.com/content/j833777550q24723/ | pmid =10234605 }}</ref> '''Sotolon''' (also known as '''sotolone''') is a ] ] and an extremely potent ], with the typical smell of ] or ] at high concentrations and ], ], or burnt sugar at lower concentrations. Sotolon is the major aroma and flavor component of fenugreek seed and ],<ref>{{cite journal |author1=Imre Blank |author2=Peter Schieberle | title =Analysis of the seasoning-like flavour substances of a commercial lovage extract | journal =Flavour and Fragrance Journal | year =1993 | volume =8 | issue = 4| pages =191–195 | doi =10.1002/ffj.2730080405 | url =http://www3.interscience.wiley.com/cgi-bin/abstract/112664676/ABSTRACT | archive-url =https://archive.today/20121216135836/http://www3.interscience.wiley.com/cgi-bin/abstract/112664676/ABSTRACT | url-status =dead | archive-date =2012-12-16 | format =abstract}}</ref> and is one of several aromatic and flavor components of ].<ref>{{cite journal | url = http://www.centreacer.qc.ca/uploaded/Publications/39_Fr.pdf | title = Caractéristiques chimiques et nutritives du sirop d'érable | language = fr | date = March 1994 | publisher = Centre de recherche, de développement et de transfert technologique acéricole}}</ref> It is also present in ], aged ], aged ] and ], ] ], roast tobacco,<ref></ref> and dried fruiting bodies of the mushroom '']''.<ref>{{cite journal | author1 =Sylvie Rapior, Françoise Fons | author2 =Jean-Marie Bessièreb | name-list-style =amp | title =The fenugreek odor of Lactarius helvus | journal =Mycologia | year =2000 | volume =92 | issue =2 | pages =305–308 | doi =10.2307/3761565 | url =http://apt.allenpress.com/aptonline/?request=get-abstract&issn=0027-5514&volume=092&issue=02&page=0305 | format =abstract | jstor =3761565 | url-status =dead | archive-url =https://web.archive.org/web/20060426185659/http://apt.allenpress.com/aptonline/?request=get-abstract&issn=0027-5514&volume=092&issue=02&page=0305 | archive-date =2006-04-26 }}</ref> 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 ], sotolon is spontaneously produced in their bodies and excreted in their urine, leading to the disease's characteristic smell.<ref>{{cite journal | author =F. Podebrad, M. Heil, S. Reichert1, A. Mosandl, A. C. Sewell and H. Böhles | title =4,5-Dimethyl-3-hydroxy-2(5H)-furanone (sotolone) — The odour of maple syrup urine disease | journal =Journal of Inherited Metabolic Disease | year =1999 | volume =22 | issue =2 | pages =107–114 | doi =10.1023/A:1005433516026 | pmid =10234605 | s2cid =6426166 | doi-access =free }}</ref>


This molecule is thought to be responsible for the mysterious maple syrup smell that has occasionally wafted over Manhattan since 2005.<ref></ref> This molecule is thought to be responsible for the ] that has occasionally wafted over ] since 2005,<ref>{{cite web | url = http://www.scientificamerican.com/blog/post.cfm?id=mystery-of-nyc-maple-syrup-smell-so-2009-02-05 | title = Mystery of NYC maple syrup smell solved! | author = John Matson | date = Feb 5, 2009 | publisher = ] News Blog}}</ref> with the source of the sotolon being a factory in New Jersey that processes the herb ].<ref>{{Cite web |title=Sotolon: The Molecule That Smells Like Pancakes, Fall, and a NYC Mystery |url=https://www.seriouseats.com/sotolon-flavor-molecule |access-date=2024-04-10 |website=Serious Eats |language=en}}</ref>

Sotolon was first isolated in 1975 from fenugreek.<ref>F. Rijkens and H. Boelens (1975) "The future of aroma research," ''Proceedings of the International Symposium on Aroma Research'', H. Maarse and P.J. Groenen, eds. (Wageningen, Netherlands: Pudoc, 1975), pp. 203-220.</ref> The compound was named in 1980 when it was found to be responsible for the flavor of raw cane sugar: {{Nihongo|''soto''|粗糖|sotō}} means "raw sugar" in ] and the ] ''-olon'' signifies that the molecule is an ] ].<ref>Tokitomo, Yukiko; Kobayashi, Akio; Yamanishi, Tei; Muraki, Shigeru (1980) "Studies on the "sugary flavor" of raw cane sugar. III. Key compound of the sugary flavor," ''Proceedings of the Japan Academy'', series B, '''56''' (7) : 457-462 ; see footnote on p. 457.</ref>

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 ] 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 <ref>{{Cite journal|last1=Freitas|first1=Ana I.|last2=Pereira|first2=Vanda|last3=Leça|first3=João M.|last4=Pereira|first4=Ana C.|last5=Albuquerque|first5=Francisco|last6=Marques|first6=José C.|date=2018-02-15|title=A Simple Emulsification-Assisted Extraction Method for the GC–MS/SIM Analysis of Wine Markers of Aging and Oxidation: Application for Studying Micro-Oxygenation in Madeira Wine|journal=Food Analytical Methods|volume=11|issue=8|language=en|pages=2056–2065|doi=10.1007/s12161-018-1176-3|issn=1936-9751|hdl=10400.13/3635|s2cid=102509460|hdl-access=free}}</ref> and single-step miniaturized liquid-liquid extraction followed by LC-MS/MS analysis <ref>{{Cite journal|title=Rapid Determination of Sotolon in Fortified Wines Using a Miniaturized Liquid-Liquid Extraction Followed by LC-MS/MS Analysis|last1=Marques|first1=José C.|last2=Pereira|first2=Ana C.|date=2018|journal=Journal of Analytical Methods in Chemistry|volume=2018|pages=4393040|language=en|last3=Gaspar|first3=João M.|last4=Leça|first4=João M.|last5=Pereira|first5=Vanda|doi=10.1155/2018/4393040|pmid=30647986|pmc=6311786|doi-access=free}}</ref>

==French ''vin jaune''==
'']'' is marked by the formation of sotolon from ].<ref>{{cite journal | doi = 10.1021/jf00058a012 | title = Optimal Conditions for the Formation of Sotolon from α-Ketobutyric Acid in the French "Vin Jaune" | year = 1995 | last1 = Thuy | first1 = Pham Thu | last2 = Elisabeth | first2 = Guichard | last3 = Pascal | first3 = Schlich | last4 = Claudine | first4 = Charpentier | journal = Journal of Agricultural and Food Chemistry | volume = 43 | issue = 10 | pages = 2616}}</ref><ref>{{cite journal | doi = 10.1007/BF02275793 | title = Quantitative determination of sotolon in wines by high-performance liquid chromatography | year = 1993 | last1 = Guichard | first1 = E. | last2 = Pham | first2 = T. T. | last3 = Etievant | first3 = P. | journal = Chromatographia | volume = 37 | issue = 9–10 | pages = 539| s2cid = 95494741 }}</ref>

==See also==
*] (Lactarius mushroom species whose maple syrup aroma derives from quabalactone III, which hydrolyzes into sotolon).


==References== ==References==
{{reflist}} {{Reflist}}


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