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Indoxyl

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Indoxyl
Indoxyl.svg
Names
Preferred IUPAC name
1H-Indol-3-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.216.308 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 689-424-0
KEGG
PubChem CID
UNII
  • InChI=1S/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H Yes check.svgY
    Key: PCKPVGOLPKLUHR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H
    Key: PCKPVGOLPKLUHR-UHFFFAOYAR
  • Oc2c1ccccc1[nH]c2
Properties
C8H7NO
Molar mass 133.14728
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Danger
H302, H311, H319, H400
P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P312, P322, P330, P337+P313, P361, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

In organic chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO. [1] [2] Indoxyl is isomeric with oxindol and is obtained as an oily liquid.

Preparation

The Heumann indigo synthesis starts from anthranilic acid:

Indoxyl-Synthese: Anthanilic acid (1) reacts with chloroacetic acid to give phenylglycine-o-carboxylic acid. When treated in molten sodium carbonate, the 2-Indoxycarboxylic acid (3) decarboxylates to give indoxyl (4) . Synthesis Indoxyl.svg
Indoxyl-Synthese: Anthanilic acid (1) reacts with chloroacetic acid to give phenylglycine-o-carboxylic acid. When treated in molten sodium carbonate, the 2-Indoxycarboxylic acid (3) decarboxylates to give indoxyl (4) .

In nature indoxyl is derived from indican, which is a glycoside. The hydrolysis of indican yields β-D-glucose and indoxyl.

Indigo dye is a product of the mild oxidation of indoxyl.

Indoxyl can be found in urine, when associated with indoxyl sulfate, a cariotoxin, which is detected by titration with Obermayer's reagent, which is a dilute solution of ferric chloride (FeCl3) in hydrochloric acid (HCl). [3]

References

  1. ↑ Katritzky, A. R.; Pozharskii, A. F. (2000). Handbook of Heterocyclic Chemistry (2nd ed.). Academic Press. ISBN   0080429882.
  2. ↑ Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry . Oxford, Oxfordshire: Oxford University Press. ISBN   0-19-850346-6.
  3. ↑ Lide, David (1998). CRC - Handbook of Chemistry and Physics. CRC press LLC. pp. Section 8 page 3. ISBN   0-8493-0479-2.
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