Furan-2-ylmethanethiol

Last updated

Furan-2-ylmethanethiol
2-Furanmethanethiol.svg
Furan-2-ylmethanethiol.png
Names
Preferred IUPAC name
(Furan-2-yl)methanethiol
Other names
  • Furan-2-ylmethanethiol
  • (2-Furanyl)methylmercaptan
  • 2-Furfurylmercaptan
  • Furfuryl mercaptan
  • 2-Furfurylthiol
  • Furfuryl thiol
  • 2-Furylmethanethiol
  • 2-Furylmethyl mercaptan
  • 2-(Mercaptomethyl)furan
Identifiers
3D model (JSmol)
383594
ChemSpider
ECHA InfoCard 100.002.390 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-628-2
MeSH furfuryl+mercaptan
PubChem CID
RTECS number
  • LU2100000
UNII
UN number 3336
  • InChI=1S/C5H6OS/c7-4-5-2-1-3-6-5/h1-3,7H,4H2 Yes check.svgY
    Key: ZFFTZDQKIXPDAF-UHFFFAOYSA-N Yes check.svgY
  • SCc1ccco1
  • SCC1=CC=CO1
Properties
C5H6OS
Molar mass 114.16 g·mol−1
AppearanceColourless liquid
Odor Roasted coffee, Caramel, Sulfurous, Waxy
Density 1.132 g cm−3
Boiling point 155 °C; 311 °F; 428 K
Vapor pressure 531 Pa
Hazards
GHS labelling:
GHS-pictogram-flamme.svg
Warning
H226
Flash point 45 °C (113 °F; 318 K)
Lethal dose or concentration (LD, LC):
100-200 mg kg−1 (mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Furan-2-ylmethanethiol (2-Furanmethanethiol) is an organic compound containing a furan substituted with a sulfanylmethyl group. It is a clear colourless liquid when pure, but it becomes yellow coloured upon prolonged standing. It possesses a strong odour of roasted coffee and a bitter taste. It is a key component of the aroma of roasted coffee. It has been identified as a trigger molecule for parosmia following COVID-19 infection. [1] [2]

Synthesis

Furan-2-ylmethanethiol is easily prepared by reacting furfuryl alcohol with thiourea in hydrochloric acid via an intermediate isothiouronium salt which is hydrolized to the thiol by heating with sodium hydroxide. [3]

Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol) Furfuryl mercaptane synthesis.png
Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol)

Related Research Articles

<span class="mw-page-title-main">Williamson ether synthesis</span> Method for preparing ethers

The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an SN2 reaction. This reaction is important in the history of organic chemistry because it helped prove the structure of ethers.

Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Furfural is only derived from lignocellulosic biomass, i.e., its origin is non-food or non-coal/oil based. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest organic chemicals available readily purified from natural precursors.

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.

<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

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.

<span class="mw-page-title-main">Coffee bean</span> Seed of the coffee plant

A coffee bean is a seed of the Coffea plant and the source for coffee. It is the pip inside the red or purple fruit. This fruit is often referred to as a coffee cherry. Just like ordinary cherries, the coffee fruit is also a so-called stone fruit. Even though the coffee beans are not technically beans, they are referred to as such because of their resemblance to true beans. The fruits; cherries or berries, most commonly contain two stones with their flat sides together. A small percentage of cherries contain a single seed, instead of the usual two. This is called a "peaberry". The peaberry occurs only between 10% and 15% of the time, and it is a fairly common belief that they have more flavour than normal coffee beans. Like Brazil nuts and white rice, coffee beans consist mostly of endosperm.

Parosmia is a dysfunctional smell detection characterized by the inability of the brain to correctly identify an odor's "natural" smell. Instead, the natural odor is usually transformed into an unpleasant aroma, typically a "burned", "rotting", "fecal", or "chemical" smell. There can also be rare instances of a pleasant odor called euosmia. The condition was rare and little-researched until it became relatively more widespread since 2020 as a side effect of COVID-19.

<span class="mw-page-title-main">Psoralen</span> Chemical compound

Psoralen is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. It is structurally related to coumarin by the addition of a fused furan ring, and may be considered as a derivative of umbelliferone. Psoralen occurs naturally in the seeds of Psoralea corylifolia, as well as in the common fig, celery, parsley, West Indian satinwood, and in all citrus fruits. It is widely used in PUVA treatment for psoriasis, eczema, vitiligo, and cutaneous T-cell lymphoma; these applications are typically through the use of medications such as Methoxsalen. Many furanocoumarins are extremely toxic to fish, and some are deposited in streams in Indonesia to catch fish.

<span class="mw-page-title-main">Hydroxymethylfurfural</span> Chemical compound

Hydroxymethylfurfural (HMF), also 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.

<span class="mw-page-title-main">Coffee roasting</span> Process of heating green coffee beans

Roasting coffee transforms the chemical and physical properties of green coffee beans into roasted coffee products. The roasting process is what produces the characteristic flavor of coffee by causing the green coffee beans to change in taste. Unroasted beans contain similar if not higher levels of acids, protein, sugars, and caffeine as those that have been roasted, but lack the taste of roasted coffee beans due to the Maillard and other chemical reactions that occur during roasting.

<span class="mw-page-title-main">Furfuryl alcohol</span> Chemical compound

Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents.

In organic chemistry, the Paal–Knorr Synthesis is a reaction used to synthesize substituted furans, pyrroles, or thiophenes from 1,4-diketones. It is a synthetically valuable method for obtaining substituted furans and pyrroles, which are common structural components of many natural products. It was initially reported independently by German chemists Carl Paal and Ludwig Knorr in 1884 as a method for the preparation of furans, and has been adapted for pyrroles and thiophenes. Although the Paal–Knorr synthesis has seen widespread use, the mechanism wasn't fully understood until it was elucidated by V. Amarnath et al. in the 1990s.

Dysosmia is a disorder described as any qualitative alteration or distortion of the perception of smell. Qualitative alterations differ from quantitative alterations, which include anosmia and hyposmia. Dysosmia can be classified as either parosmia or phantosmia. Parosmia is a distortion in the perception of an odorant. Odorants smell different from what one remembers. Phantosmia is the perception of an odor when no odorant is present. The cause of dysosmia still remains a theory. It is typically considered a neurological disorder and clinical associations with the disorder have been made. Most cases are described as idiopathic and the main antecedents related to parosmia are URTIs, head trauma, and nasal and paranasal sinus disease. Dysosmia tends to go away on its own but there are options for treatment for patients that want immediate relief.

<span class="mw-page-title-main">Achmatowicz reaction</span> Organic synthesis

The Achmatowicz reaction, also known as the Achmatowicz rearrangement, is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by the Polish Chemist Osman Achmatowicz Jr. in 1971 furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute sulfuric acid. Additional reaction steps, alcohol protection with methyl orthoformate and boron trifluoride) and then ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.

Furfurylamine is an aromatic amine typically formed by the reductive amination of furfural with ammonia.

<span class="mw-page-title-main">2,2-Di-2-furylpropane</span> Chemical compound

2,2-Di-2-furylpropane is a condensation product of furan and acetone. It is a relatively high boiling liquid and is a precursor to the rubber additive bis(tetrahydrofuryl)propane used in the manufacture of high vinyl content rubber for high performance tires.

<span class="mw-page-title-main">Coffee furanone</span> Chemical compound

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.

<span class="mw-page-title-main">2-Furoic acid</span> Chemical compound

2-Furoic acid is an organic compound, consisting of a furan ring and a carboxylic acid side-group. Along with other furans, its name is derived from the Latin word furfur, meaning bran, from which these compounds were first produced. The salts and esters of furoic acids are known as furoates. 2-Furoic acid is most widely encountered in food products as a preservative and a flavouring agent, where it imparts a sweet, earthy flavour.

<span class="mw-page-title-main">2-Furoyl chloride</span> Chemical compound

2-Furoyl chloride is an acyl chloride of furan. It takes the form of a corrosive liquid, which is more irritating to the eyes than benzoyl chloride. 2-Furoyl chloride is a useful pharmaceutical intermediate and is used in the synthesis of mometasone furoate, an antiinflammatory prodrug used in the treatment of skin disorders, hay fever and asthma.

Dionisios G. Vlachos is an American chemical engineer, the Allan & Myra Ferguson Endowed Chair Professor of Chemical Engineering at the University of Delaware and director of the Catalysis Center for Energy Innovation, a U.S. Department of Energy - Energy Frontiers Research Center. Throughout his career at University of Delaware and the University of Minnesota, he has advanced the study of catalysts and reaction engineering including catalytic applications in biomass utilization, alkane conversion and zeolites. He is a fellow of the American Association for the Advancement of Science and recipient of the Wilhelm Award of the American Institute of Chemical Engineers (2011).

<span class="mw-page-title-main">Furan resin</span>

Furan resin refers to polymers produced from various furan compounds, of which the most common starting materials are furfuryl alcohol and furfural. In the resin and in the cured polyfurfurol, the furan rings are not connected by conjugation. The resins are generally used as binders for sand castings. The furan monomer is typically converted to a free-flowing resin with mild acid catalysis. Curing is achieved using strong acid.

References

  1. Parker JK, Kelly CE, Gane SB (5 February 2021). "Molecular Mechanism of Parosmia". p. 21251085. medRxiv   10.1101/2021.02.05.21251085 .
  2. Devlin H (25 May 2022). "Scientists identify 'trigger molecule' for Covid-related changes to smell". The Guardian.
  3. "Preparation of furfuryl mercaptane". Organic Syntheses. 35: 66. 1955. doi:10.15227/orgsyn.035.0066.