Structural Formula Vector Image
Title: Hematoxylin
CAS Registry Number: 517-28-2
CAS Name: cis-(+)-7,11b-Dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol
Additional Names: hematoxiline; hydroxybrazilin; hydroxybrasilin
Molecular Formula: C16H14O6
Molecular Weight: 302.28
Percent Composition: C 63.57%, H 4.67%, O 31.76%
Literature References: From the heart-wood of logwood (Haematoxylon campechianum Linn., Leguminosae): Chevreul, Ann. Chim. Phys. 82, 54, 126 (1810). Structure: Perkin, Robinson, J. Chem. Soc. 93, 489 (1908). Synthesis: Dann, Hofmann, Angew. Chem. 75, 1125 (1963); Morsingh, Robinson, Tetrahedron 26, 281 (1970); Kirkiacharian, Billet, Bull. Soc. Chim. Fr. 1972, 3292. Stereochemistry: Craig et al., J. Org. Chem. 30, 1573 (1965). Spectroscopic and physico-chemical properties: C. Bettinger, H. W. Zimmerman, Histochemistry 95, 279 (1991). Prepn for staining: R. B. Bosma et al., J. Histotechnol. 16, 371 (1993). Use in determn of ruthenium: A.-A. Y. El-Sayed, Fresenius J. Anal. Chem. 349, 830 (1994). Review: Robinson, Bull. Soc. Chim. Fr. 1958, 125. Review of theory and application as histological stain: B. B. Hrapchak, Am. J. Med Technol. 42, 371-379 (1976).
Derivative Type: Trihydrate
Properties: White to yellowish crystals; redden on exposure to light, mp 100-120°; also stated as 140°. Slightly sol in cold water, ether; sol in hot water, hot alc, also in alkali hydroxides, borax, glycerol. Its solns darken on standing.
Melting point: mp 100-120°
Use: Chiefly as a stain in microscopy; also in manufacture of ink.

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