Orcinol is an organic compound with the formula CH3C6H3(OH)2. It occurs in many species of
lichen
A lichen ( , ) is a composite organism that arises from algae or cyanobacteria living among filaments of multiple fungi species in a mutualistic relationship.Roccella tinctoria'' and ''
Lecanora
''Lecanora'' is a genus of lichen commonly called rim lichens.Field Guide to California Lichens, Stephen Sharnoff, Yale University Press, 2014, Lichens in the genus '' Squamarina'' are also called rim lichens. Members of the genus have roughly c ...
''. Orcinol has been detected in the "toxic glue" of the ant species ''
Camponotus saundersi
''Colobopsis saundersi'', synonym ''Camponotus saundersi'', is a species of ant found in Malaysia and Brunei, belonging to the genus '' Colobopsis''. A worker can explode suicidally and aggressively as an ultimate act of defense, an ability it h ...
''. It is a colorless solid. It is related to
resorcinol
Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or '' meta''-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in ...
, 1,3-C6H4(OH)2.
Synthesis and reactions
Orcinol was first prepared by dehydroacetic acid, a conversion that involved ring-opening of the pyrone to a triketone. This early experiment helped establish the rich condensation chemistry of
polyketide
Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynth ...
s.
It can be obtained by fusing extract of
aloe
''Aloe'' (; also written ''Aloë'') is a genus containing over 650 species of flowering succulent plants.WFO (2022): Aloe L. Published on the Internet;http://www.worldfloraonline.org/taxon/wfo-4000001341. Accessed on: 06 Nov 2022 The most wi ...
s with
potash
Potash () includes various mined and manufactured salts that contain potassium in water- soluble form.
, followed by acidification.
It undergoes O-
methylation
In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These ...
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
in some chemical tests for
pentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.Bial's Test. It may be synthesized from
toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) ...
sodium
Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...
. It crystallizes in colorless prisms with one molecule of water, which redden on exposure to air.
Ferric chloride
Iron(III) chloride is the inorganic compound with the formula . Also called ferric chloride, it is a common compound of iron in the +3 oxidation state. The anhydrous compound is a crystalline solid with a melting point of 307.6 °C. The col ...
gives a bluish-violet coloration with the aqueous solution. Unlike
resorcinol
Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or '' meta''-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in ...
it does not give a
fluorescein
Fluorescein is an organic compound and dye based on the xanthene tricyclic structural motif, formally belonging to triarylmethine dyes family. It is available as a dark orange/red powder slightly soluble in water and alcohol. It is widely used ...
with
phthalic anhydride
Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commer ...
. Oxidation of the ammoniacal solution gives orcein, C28H24N2O7, the chief constituent of the
natural dye
Natural dyes are dyes or colorants derived from plants, invertebrates, or minerals. The majority of natural dyes are vegetable dyes from plant sources— roots, berries, bark, leaves, and wood—and other biological sources such as fungi.
Ar ...
archil Archil may refer to:
People
Archil, a historical Georgian male given name (including people with that name)
Georgian Royalty
*5th-century Archil of Iberia
*8th century prince and martyr Archil of Kakheti
*16th-century Archil, Prince of Mukhra ...
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Is ...
beech
Beech (''Fagus'') is a genus of deciduous trees in the family Fagaceae, native to temperate Europe, Asia, and North America. Recent classifications recognize 10 to 13 species in two distinct subgenera, ''Engleriana'' and ''Fagus''. The ''Engl ...
-wood tar.
:
Production from shale oil
Orcinol is also found in
shale oil
Shale oil is an unconventional oil produced from oil shale rock fragments by pyrolysis, hydrogenation, or thermal dissolution. These processes convert the organic matter within the rock ( kerogen) into synthetic oil and gas. The resulting ...
produced from Kukersite oil shale. It is the main water-soluble phenol in the oil, and has been extracted and refined industrially by
Viru Keemia Grupp
Viru Keemia Grupp (VKG) is an Estonian holding group of oil shale industry, power generation, and public utility companies.
History
After Estonia gained independence, the state owned oil shale enterprise, Riigi Põlevkivitööstus ( en, Eston ...