CHEBI:51686 - haematoxylin

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ChEBI Name haematoxylin
ChEBI ID CHEBI:51686
Definition An organic heterotetracyclic compound 7,11b-dihydroindeno[2,1-c]chromene carrying five hydroxy substituents at positions 3, 4, 6a, 9 and 10. The most important and most used dye in histology, histochemistry, histopathology and in cytology.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H14O6
Net Charge 0
Average Mass 302.27876
Monoisotopic Mass 302.07904
InChI InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2
InChIKey WZUVPPKBWHMQCE-UHFFFAOYSA-N
SMILES Oc1cc2CC3(O)COc4c(O)c(O)ccc4C3c2cc1O
Metabolite of Species Details
Haematoxylum campechianum (NCBI:txid321551) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): histological dye
A dye used in microscopic or electron microscopic examination of cells and tissues to give contrast and to highlight particular features of interest, such as nuclei and cytoplasm.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing haematoxylin (CHEBI:51686) has role histological dye (CHEBI:77178)
haematoxylin (CHEBI:51686) has role plant metabolite (CHEBI:76924)
haematoxylin (CHEBI:51686) is a organic heterotetracyclic compound (CHEBI:38163)
haematoxylin (CHEBI:51686) is a oxacycle (CHEBI:38104)
haematoxylin (CHEBI:51686) is a polyphenol (CHEBI:26195)
haematoxylin (CHEBI:51686) is a tertiary alcohol (CHEBI:26878)
Incoming (−)-haematoxylin (CHEBI:51684) is a haematoxylin (CHEBI:51686)
(+)-haematoxylin (CHEBI:5601) is a haematoxylin (CHEBI:51686)
IUPAC Name
7,11b-dihydroindeno[2,1-c]chromene-3,4,6a,9,10(6H)-pentol
Synonyms Sources
7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol ChemIDplus
C.I. 75290 ChEBI
Hämatoxylin ChEBI
hematoxilina ChEBI
hematoxylin ChemIDplus
hématoxyline ChEBI
Natural black 1 ChEBI
Registry Numbers Types Sources
17647-60-8 CAS Registry Number ChemIDplus
91399 Reaxys Registry Number Reaxys
91399 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11677809 PubMed citation Europe PMC
12751322 PubMed citation Europe PMC
18411731 PubMed citation Europe PMC
19579146 PubMed citation Europe PMC
Last Modified
27 October 2015
General Comment
2015-10-27 Also see: http://www.arpapress.com/Volumes/JPCS/Vol1/JPCS_1_05.pdf