In
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clay ...
, the aromatic alcohols or aryl-alcohols are a class of
chemical compounds
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
containing a
hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydrox ...
group
A group is a number of persons or things that are located, gathered, or classed together.
Groups of people
* Cultural group, a group whose members share the same cultural identity
* Ethnic group, a group whose members share the same ethnic ide ...
(—
O H)
bonded indirectly to an
aromatic hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grou ...
group, in contrast to the
phenols
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds ...
, where the hydroxyl group is bonded directly to an aromatic carbon atom.
Aromatic alcohols are produced by the yeast ''
Candida albicans
''Candida albicans'' is an opportunistic pathogenic yeast that is a common member of the human gut flora. It can also survive outside the human body. It is detected in the gastrointestinal tract and mouth in 40–60% of healthy adults. It is usua ...
''. They are also found in
beer
Beer is one of the oldest and the most widely consumed type of alcoholic drink in the world, and the third most popular drink overall after water and tea. It is produced by the brewing and fermentation of starches, mainly derived from cer ...
. These molecules are
quorum sensing
In biology, quorum sensing or quorum signalling (QS) is the ability to detect and respond to cell population density by gene regulation. As one example, QS enables bacteria to restrict the expression of specific genes to the high cell densities a ...
compounds for ''
Saccharomyces cerevisiae
''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungus microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have been o ...
''.
[Quorum Sensing: Alcohols in a Social Situation.Deborah A. Hogan, Current Biology, 20 June 2006, Volume 16, Issue 12, R457-R458, ]
Metabolism
Aryl-alcohol dehydrogenase uses an aromatic alcohol and NAD
+ to produce an
aromatic aldehyde, NADH and H
+.
Aryl-alcohol dehydrogenase (NADP+) uses an aromatic alcohol and NADP
+ to produce an
aromatic aldehyde, NADPH and H
+.
Aryldialkylphosphatase (also known as organophosphorus hydrolase, phosphotriesterase, and paraoxon hydrolase) uses an aryl dialkyl phosphate and H
2O to produce dialkyl phosphate and an aryl alcohol.
Examples
*
Tryptophol
Tryptophol is an aromatic alcohol that induces sleep in humans. It is found in wine as a secondary product of ethanol fermentation. It was first described by Felix Ehrlich in 1912. It is also produced by the trypanosomal parasite in sleeping si ...
*
Tyrosol
Tyrosol is an organic compound with the formula . Classified as a phenylethanoid, i.e. a derivative of phenethyl alcohol, It is found in a variety of natural sources. The compound is colorless solid. The principal source in the human diet is olive ...
*
Phenethyl alcohol
Phenethyl alcohol, or 2-phenylethanol, is the organic compound that consists of a phenethyl group (C6H5CH2CH2) attached to OH. It is a colourless liquid that is slightly soluble in water (2 ml/100 ml H2O), but miscible with most organic solvents. ...
(Phenylethanol)
*
Benzyl alcohol
Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liqui ...
See also
*
Phenolic acid
Phenolic acids or phenolcarboxylic acids are types of aromatic acid compounds. Included in that class are substances containing a phenolic ring and an organic carboxylic acid function (C6-C1 skeleton). Two important naturally occurring types of ph ...
*
Aromatic acid
Aromatic acids are a type of aromatic compound. Included in that class are substances containing an aromatic ring and an organic acid functional group.
There are several categories of aromatic acids including:
*Phenolic acids: substances containin ...
References
{{reflist
Hydroxyarenes