4-Methylcatechol

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4-Methylcatechol
4-Methylcatechol.svg
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.559 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-214-5
KEGG
PubChem CID
UNII
  • InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
    Key: ZBCATMYQYDCTIZ-UHFFFAOYSA-N
  • CC1=CC(=C(C=C1)O)O
Properties
C7H8O2
Molar mass 124.139 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H312, H315, H319, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [1]

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. [2]

Production and occurrence

Calone, a derivative of 4-methylcatechol, is known in the fragrance industry as "watermelon ketone" for its distinctive odor. Calone V1.svg
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.[ citation needed ]

Being structurally related to lignans, it is contributes to the aerosol generate by combustion of wood. [4]

It is a component of castoreum, the exudate from the castor sacs of the mature beaver. [5]

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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