4-Ethylguaiacol

Last updated
4-Ethylguaiacol
4-Ethylguaiacol.svg
Names
Preferred IUPAC name
4-Ethyl-2-methoxyphenol
Other names
p-Ethylguaiacol
Homocresol
Guaiacyl ethane
2-Methoxy-4-ethylphenol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.637 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3 Yes check.svgY
    Key: CHWNEIVBYREQRF-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3
    Key: CHWNEIVBYREQRF-UHFFFAOYAE
  • Oc1ccc(cc1OC)CC
Properties
C9H12O2
Molar mass 152.193 g·mol−1
AppearanceColorless liquid
Density 1064 kg/m3 (20 °C) [1]
Melting point 15 °C (59 °F; 288 K)
Boiling point 235.1 °C (455.2 °F; 508.2 K) [1]
Hazards
GHS labelling: [2]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P302+P352, P305+P351+P338
NFPA 704 (fire diamond)
2
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

4-Ethylguaiacol, often abbreviated to 4-EG, is a phenolic compound with the molecular formula C9H12O2. It can be produced in wine and beer by Brettanomyces . [3] It is also frequently present in bio-oil produced by pyrolysis of lignocellulosic biomass. [4]

Contents

Winemaking

It is produced along with 4-ethylphenol (4-EP) in wine and beer by the spoilage yeast Brettanomyces . [3] When it is produced by the yeast to concentrations greater than the sensory threshold of >600 µg/L, it can contribute bacon, spice, clove, or smoky aromas to the wine. On their own these characters can be quite attractive in a wine, however as the compound usually occurs with 4-EP whose aromas can be more aggressive, the presence of the compound often signifies a wine fault. The ratio in which 4-EP and 4-EG are present can greatly affect the organoleptic properties of the wine.

Bio-oil

4-Ethylguaiacol can also be produced by pyrolysis of lignocellulosic biomass. It is produced from the lignin, along with many of the other phenolic compounds present in bio-oil. In particular, 4-ethylguaiacol is derived from guaiacyl in the lignin. [4]

See also

Related Research Articles

Lignin Structural phenolic polymer in plant cell walls

Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidity and do not rot easily. Chemically, lignins are polymers made by cross-linking phenolic precursors.

<i>Brettanomyces</i> Genus of fungi

Brettanomyces is a non-spore forming genus of yeast in the family Saccharomycetaceae, and is often colloquially referred to as "Brett". The genus name Dekkera is used interchangeably with Brettanomyces, as it describes the teleomorph or spore forming form of the yeast, but is considered deprecated under the one fungus, one name change. The cellular morphology of the yeast can vary from ovoid to long "sausage" shaped cells. The yeast is acidogenic, and when grown on glucose rich media under aerobic conditions, produces large amounts of acetic acid. Brettanomyces is important to both the brewing and wine industries due to the sensory compounds it produces.

Biorefinery

A biorefinery is a refinery that converts biomass to energy and other beneficial byproducts. The International Energy Agency Bioenergy Task 42 defined biorefining as "the sustainable processing of biomass into a spectrum of bio-based products and bioenergy ". As refineries, biorefineries can provide multiple chemicals by fractioning an initial raw material (biomass) into multiple intermediates that can be further converted into value-added products. Each refining phase is also referred to as a "cascading phase". The use of biomass as feedstock can provide a benefit by reducing the impacts on the environment, as lower pollutants emissions and reduction in the emissions of hazard products. In addition, biorefineries are intended to achieve the following goals:

  1. Supply the current fuels and chemical building blocks
  2. Supply new building blocks for the production of novel materials with disruptive characteristics
  3. Creation of new jobs, including rural areas
  4. Valorization of waste
  5. Achieve the ultimate goal of reducing GHG emissions

A wine fault or defect is an unpleasant characteristic of a wine often resulting from poor winemaking practices or storage conditions, and leading to wine spoilage. Many of the compounds that cause wine faults are already naturally present in wine but at insufficient concentrations to be of issue. In fact, depending on perception, these concentrations may impart positive characters to the wine. However, when the concentration of these compounds greatly exceeds the sensory threshold, they replace or obscure the flavors and aromas that the wine should be expressing. Ultimately the quality of the wine is reduced, making it less appealing and sometimes undrinkable.

Guaiacol is a naturally-occurring organic compound with the formula C6H4(OH)(OCH3). Although it is biosynthesized by a variety of organisms, this aromatic oil is usually derived from guaiacum or wood creosote. It is also found in essential oils from celery seeds, tobacco leaves, orange leaves, and lemon peels. The pure substance is colorless, but samples become yellow upon exposure to air and light. Guaiacol is present in wood smoke, resulting from the pyrolysis of lignin. The compound contributes to the flavor of many substances such as whisky and roasted coffee.

3-Methylbutanoic acid Carboxylic acid with chemical formula (CH3)2CHCH2CO2H CH3CH2

3-Methylbutanoic acid, also known as β-methylbutyric acid or more commonly isovaleric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.

<i>p</i>-Coumaric acid Chemical compound

p-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acid—o-coumaric acid, m-coumaric acid, and p-coumaric acid—that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. p-Coumaric acid exists in two forms trans-p-coumaric acid and cis-p-coumaric acid.

4-Ethylphenol (4-EP) is an organic compound with the formula C2H5C6H4OH. It is one of three isomeric ethylphenols. A white solid, it occurs as an impurity in xylenols and as such is used in the production of some commercial phenolic resins. It is also a precursor to 4-vinylphenol.

Pyrolysis oil, sometimes also known as bio-crude or bio-oil, is a synthetic fuel under investigation as substitute for petroleum. It is obtained by heating dried biomass without oxygen in a reactor at a temperature of about 500 °C with subsequent cooling. Pyrolysis oil is a kind of tar and normally contains levels of oxygen too high to be considered a pure hydrocarbon. This high oxygen content results in non-volatility, corrosiveness, immiscibility with fossil fuels, thermal instability, and a tendency to polymerize when exposed to air. As such, it is distinctly different from petroleum products. Removing oxygen from bio-oil or nitrogen from algal bio-oil is known as upgrading.

Lignocellulosic biomass

Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of biofuels. It is composed of two kinds of carbohydrate polymers, cellulose and hemicellulose, and an aromatic-rich polymer called lignin. Each has distinct chemical behavior. Being a composite of three very different components makes the processing of lignocellulose challenging. The highly evolved resistance to degradation or even separation is referred to as recalcitrance. Overcoming this recalcitrance to produce useful, high value products requires a combination of heat, chemicals, enzymes, and microorganisms. These carbohydrate-containing polymers contain different sugar monomers and they are covalently bound to lignin. Lignocellulosic biomass can be broadly classified into virgin biomass, waste biomass, and energy crops. Virgin biomass includes all naturally occurring terrestrial plants such as trees, bushes and grass. Waste biomass is produced as a low value byproduct of various industrial sectors such as agriculture and forestry. Energy crops are crops with high yield of lignocellulosic biomass produced to serve as a raw material for production of second generation biofuel; examples include switchgrass and Elephant grass.

Syringol Chemical compound

Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, although typical samples are brown owing to air-oxidized impurities. Together with guaiacol, syringol and its derivatives are produced by the pyrolysis of lignin. Specifically, syringol is derived from the thermal decomposition of the sinapyl alcohol component. As such, syringol is an important component of wood smoke.

Second-generation biofuels, also known as advanced biofuels, are fuels that can be manufactured from various types of non-food biomass. Biomass in this context means plant materials and animal waste used especially as a source of fuel.

Clarification and stabilization of wine Wine clarification and stabilisation

In winemaking, clarification and stabilization are the processes by which insoluble matter suspended in the wine is removed before bottling. This matter may include dead yeast cells (lees), bacteria, tartrates, proteins, pectins, various tannins and other phenolic compounds, as well as pieces of grape skin, pulp, stems and gums. Clarification and stabilization may involve fining, filtration, centrifugation, flotation, refrigeration, pasteurization, and/or barrel maturation and racking.

Wine chemistry

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4.

4-Vinylphenol is an organic compound with the formula C2H3C6H4OH. It is the most studied of the three isomeric vinylphenols. It is a white volatile solid.

Yeast in winemaking Yeasts used for alcoholic fermentation of wine

The role of yeast in winemaking is the most important element that distinguishes wine from grape juice. In the absence of oxygen, yeast converts the sugars of wine grapes into alcohol and carbon dioxide through the process of fermentation. The more sugars in the grapes, the higher the potential alcohol level of the wine if the yeast are allowed to carry out fermentation to dryness. Sometimes winemakers will stop fermentation early in order to leave some residual sugars and sweetness in the wine such as with dessert wines. This can be achieved by dropping fermentation temperatures to the point where the yeast are inactive, sterile filtering the wine to remove the yeast or fortification with brandy or neutral spirits to kill off the yeast cells. If fermentation is unintentionally stopped, such as when the yeasts become exhausted of available nutrients and the wine has not yet reached dryness, this is considered a stuck fermentation.

4-Hydroxycinnamate decarboxylase is an enzyme that uses p-coumaric acid to produce 4-ethylphenol.

Hydrothermal liquefaction (HTL) is a thermal depolymerization process used to convert wet biomass, and other macromolecules, into crude-like oil under moderate temperature and high pressure. The crude-like oil has high energy density with a lower heating value of 33.8-36.9 MJ/kg and 5-20 wt% oxygen and renewable chemicals.

Metschnikowia pulcherrima is a ubiquitous species of yeast, with numerous strains, belonging to the family Metschnikowiaceae, and found on grapes, cherries, flowers, spoiled fruit and consequently carried by fruit flies. It is a non-Saccharomyces yeast and plays an important role in the vinification of wine when it is present on grapes or winery equipment, and has historically seen use in South Africa’s wine industry. It is also being studied at the University of Bath as a possible alternative to the use of Palm oil, and early results show promise. M. pulcherrima is ovoid to ellipsoidal in shape and reproduces by budding. Its cells are globose and thick-walled, holding a single, large oil droplet of high refractive index. As the result of incomplete budding where cells remain attached after division, pseudohyphae may form under anaerobic conditions.

Levoglucosenone Chemical compound

Levoglucosenone is a bridged, unsaturated heterocyclic ketone formed from levoglucosan by loss of two molecules of water. It is the major component produced during the acid-catalysed pyrolysis of cellulose, D-glucose, and levoglucosan.

References

  1. 1 2 Mozaffari, Parsa; Järvik, Oliver; Baird, Zachariah Steven (2020-10-28). "Vapor Pressures of Phenolic Compounds Found in Pyrolysis Oil". Journal of Chemical & Engineering Data. 65 (11): 5559–5566. doi:10.1021/acs.jced.0c00675. ISSN   0021-9568. S2CID   228958726.
  2. GHS: Sigma-Aldrich W243604
  3. 1 2 Caboni, Pierluigi; Sarais, Giorgia; Cabras, Marco; Angioni, Alberto (2007). "Determination of 4-Ethylphenol and 4-Ethylguaiacol in Wines by LC-MS-MS and HPLC-DAD-Fluorescence". Journal of Agricultural and Food Chemistry. 55 (18): 7288–93. doi:10.1021/jf071156m. PMID   17676867.
  4. 1 2 Lyu, Gaojin; Wu, Shubin; Zhang, Hongdan (2015). "Estimation and Comparison of Bio-Oil Components from Different Pyrolysis Conditions". Frontiers in Energy Research. 3. doi: 10.3389/fenrg.2015.00028 . ISSN   2296-598X.