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4-Methylcatechol

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(Redirected from 4-methyl-1,2-dihydroxybenzene)

4-Methylcatechol
Names
Preferred IUPAC name 4-Methylbenzene-1,2-diol
Other names 4-Methyl-1,2-dihydroxybenzene
3,4-Dihydroxytoluene
Homocatechol
4-Methyl-1,2-benzenediol
Homopyrocatechol
p-Methylcatechol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.559 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CC1=CC(=C(C=C1)O)O
Properties
Chemical formula C7H8O2
Molar mass 124.139 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

4-Methylcatechol is an organic compound with the formula CH3C6H3(OH)2 A white solid, it is one of the isomers of methylbenzenediol.

Metabolism

The enzyme cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate dehydrogenase uses cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate and NAD(P) to produce 4-methylcatechol, NADH, NADPH and CO2.

Related compounds

Members of the monocot subfamily Amaryllidoideae present a unique type of alkaloids, the norbelladine alkaloids, which are 4-methylcatechol derivatives combined with tyrosine. They are responsible for the poisonous properties of a number of the species. Over 200 different chemical structures of these compounds are known, of which 79 or more are known from Narcissus alone.

Production and occurrence

Calone, a derivative of 4-methylcatechol, is known in the fragrance industry as "watermelon ketone" for its distinctive odor.

The brand of low-temperature coke used as a smokeless fuel Coalite obtains homocatechol from ammoniacal liquor by solvent extraction, distillation and crystallisation.

Being structurally related to lignans, it is contributes to the aerosol generate by combustion of wood.

It is a component of castoreum, the exudate from the castor sacs of the mature beaver.

See also

References

  1. Whited GM, McCombie WR, Kwart LD, Gibson DT (1986). "Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid". J. Bacteriol. 166 (3): 1028–39. doi:10.1128/jb.166.3.1028-1039.1986. PMC 215228. PMID 3711022.
  2. Martin, S.F. 1987. The Amaryllidaceae Alkaloids. In.: Arnold Brossi (ed.) The Alkaloids, Chapter 3. Academic Press.
  3. Panten J, Surburg H (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
  4. Rogge WF, Hildemann LM, Mazurek MA, Cass GR, Simoneit, BRT (1998). "Sources of Fine Organic Aerosol. 9. Pine, Oak, and Synthetic Log Combustion in Residential Fireplaces". Environmental Science & Technology. 32 (1): 13–22. Bibcode:1998EnST...32...13R. doi:10.1021/es960930b.
  5. Pheromonal activity of single castoreum constituents in beaver,Castor canadensis., Müller-Schwarze, D and Houlihan, P.W., Journal of Chemical Ecology, April 1991, Volume 17, Number 4, Springer Netherlands, doi:10.1007/BF00994195
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