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Indigo dye information


Indigo
Lump of Indian indigo dye
Skeletal formula of indigo dye
Ball-and-stick model of the indigo dye molecule
Names
Preferred IUPAC name
[2(2')E]-[2,2'-Biindolylidene]-3,3'(1H,1'H)-dione
Other names
2,2'-Bis(2,3-dihydro-3-oxoindolyliden), Indigotin
Identifiers
CAS Number
  • 64784-13-0 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL599552 checkY
ChemSpider
  • 4477009 checkY
ECHA InfoCard 100.006.898 Edit this at Wikidata
PubChem CID
  • 10215
RTECS number
  • DU2988400
UNII
  • 1G5BK41P4F checkY
CompTox Dashboard (EPA)
  • DTXSID3026279 Edit this at Wikidata
InChI
  • InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17-18H/b14-13+ checkY
    Key: COHYTHOBJLSHDF-BUHFOSPRSA-N checkY
  • InChI=1/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17-18H/b14-13+
    Key: COHYTHOBJLSHDF-BUHFOSPRBQ
SMILES
  • c1ccc2c(c1)C(=O)/C(=C\3/C(=O)c4ccccc4N3)/N2
Properties
Chemical formula
C16H10N2O2
Molar mass 262.27 g/mol
Appearance dark blue crystalline powder
Density 1.199 g/cm3
Melting point 390 to 392 °C (734 to 738 °F; 663 to 665 K)
Boiling point decomposes
Solubility in water
990 µg/L (at 25 °C)
Related compounds
Related compounds
Indoxyl
Tyrian purple
Indican
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Indigo dye is an organic compound with a distinctive blue color. Indigo is a natural dye extracted from the leaves of some plants of the Indigofera genus, in particular Indigofera tinctoria. Dye-bearing Indigofera plants were commonly grown and used throughout the world, particularly in Asia, with the production of indigo dyestuff economically important due to the historical rarity of other blue dyestuffs.[1]

Most indigo dye produced today is synthetic, constituting around 80,000 tonnes each year, as of 2023.[2] It is most commonly associated with the production of denim cloth and blue jeans, where its properties allow for effects such as stone washing and acid washing to be applied quickly, which is why clothing made with natural Indigo dye tends to be more expensive.

  1. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  2. ^ Linke, Julia A.; Rayat, Andrea; Ward, John M. (2023). "Production of indigo by recombinant bacteria". Bioresources and Bioprocessing. 10 (1): 20. doi:10.1186/s40643-023-00626-7. ISSN 2197-4365. PMC 10011309. PMID 36936720.

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also called true indigo, is a species of plant from the bean family that was one of the original sources of indigo dye. True indigo is a shrub 1–2 metres...

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purple-blue indigo dye. Ancient Mediterranean cultures, including the Minoans, Canaanites/Phoenicians, Hebrews, and classical Greeks created dyes from the...

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the dye indigo. Scraps of Indigo-dyed fabric likely dyed with plants from the genus Indigofera discovered at Huaca Prieta predate Egyptian indigo-dyed...

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However, the dye can cause a potentially dangerous increase in blood pressure in some cases. Although not absorbed by the cells, indigo carmine stain...

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in India and China as a source of indigo dye, which is also known as Assam indigo. In addition to being used for dye, it is also used in the traditional...

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isomer (more precisely is position isomer) of indigo dye. Indirubin is a chemical constituent of indigo naturalis (also known as qing dai 青黛), which has...

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rice, kapok, sisal, and species in the genus Indigofera, used to produce indigo dye. The longer a crop's harvest period, the more efficient plantations become...

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