Orcinol

Orcinol[1]
IUPAC name 5-Methylbenzene-1,3-diol
Other names 5-Methylresorcinol 3,5-Toluenediol Orcin 5-Methyl-1,3-benzenediol 3,5-Dihydroxytoluene
Identifiers
CAS number	504-15-4 Y
PubChem	10436
ChemSpider	13839080 N
UNII	534PMB3438 N
Jmol-3D images	Image 1
SMILES CC1=CC(=CC(=C1)O)O
Properties
Molecular formula	C7H8O2
Molar mass	124.13 g/mol (anhydr.)
Appearance	Crystalline
Melting point	110.0-110.5 °C – 107 °C (anhydr.)
Boiling point	290 °C (289.5 °C)
Solubility in water	Miscible
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Orcinol is a natural phenolic organic compound that occurs in many species of lichens^[2] including Rocella tinctoria and Lecanora. It can be formed by fusing extract of aloes with potash.

It is used in the production of the dye orcein and as a reagent in some chemical tests for pentoses, such as Bial's Test. It may be synthesized from toluene; more interesting is its production when acetone dicarboxylic ester is condensed with the aid of sodium. It crystallizes in colorless prisms with one molecule of water, which redden on exposure to air. Ferric chloride gives a bluish-violet coloration with the aqueous solution. Unlike resorcinol it does not give a fluorescein with phthalic anhydride. Oxidation of the ammoniacal solution gives orcein, C₂₈H₂₄N₂O₇, the chief constituent of the natural dye archil. Homo-pyrocatechin is an isomer (CH1: OH: OH= 1 3 :4), found as its methyl ether (creosol) in beech-wood tar.

Orcinol

See also

• Orcinol 2-monooxygenase
• Orsellinate decarboxylase
• Resorcinol

References

1. ^ Merck Index, 11th Edition, 6819.
2. ^ Robiquet: „Essai analytique des lichens de l’orseille“, Annales de chimie et de physique, 1829, 42, p. 236–257.

•  This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press. 

This article about a natural phenol is a stub. You can help Wikipedia by expanding it.v · Categories: Natural resorcinols Natural phenol stubs Wikimedia Foundation. 2010. Игры ⚽ Нужно решить контрольную? The Silent Passenger The Burning Season (Primordial album) Look at other dictionaries: Orcinol — Structure de l orcinol Général Nom IUPAC 3,5 dihydroxytoluène …   Wikipédia en Français orcinol — ● orcinol nom masculin ou orcine nom féminin Dérivé dihydroxylé du méthylbenzène. (Présent dans de nombreux lichens, il a des propriétés voisines de celles du résorcinol.) ⇒ORCINE, subst. fém.; ORCINOL, subst. masc. CHIM. Diphénol dérivé du… …   Encyclopédie Universelle orcinol — [ôr′sinôr′sə nôl΄, ôr′sənōl΄] n. [< It orcello,ARCHIL + IN1 + OL1] a colorless, crystalline compound, C6H3·CH3 (OH) 2, that becomes red in air, obtained from aloes, lichens, etc. and used as a medicine, in dyes, etc.: also orcin [ôr′sin] …   English World dictionary orcinol — orcinolis statusas T sritis chemija formulė (HO)₂C₆H₃CH₃ atitikmenys: angl. orcinol rus. орсин ryšiai: sinonimas – 5 metil 1,3 benzendiolis …   Chemijos terminų aiškinamasis žodynas Orcinol 2-monooxygenase — Identifiers EC number 1.14.13.6 CAS number 37217 34 8 …   Wikipedia orcinol — /awr seuh nawl , nol /, n. Chem. a white, crystalline, water soluble solid, C7H8O2, sweet but unpleasant in taste, that reddens on exposure to air: obtained from many lichens or produced synthetically and used chiefly as a reagent for certain… …   Universalium orcinol — noun A natural phenolic organic compound that occurs in many species of lichen, used in the production of orcein and as a reagent in some chemical tests for pentoses …   Wiktionary orcinol — 3,5 Dihydroxytoluene; the parent substance of the natural dye orcein, obtained from certain colorless lichens (Lecanora tinctoria, Rocella tinctoria) by treatment with boiling water; used as an external antiseptic in various skin diseases and in… …   Medical dictionary orcinol — n. crystalline substance that is found in many lichens and becomes red upon exposure to air (used in the production of dyes) …   English contemporary dictionary orcinol — [ ɔ:sɪnɒl] noun Chemistry a crystalline compound extracted from orchil, used to make dyes. Origin C19: from mod. L. orcina, from Ital. orcello orchil …   English new terms dictionary 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”