Solvent Black 3

Solvent Black 3 is an azo dye.[1] It is a non-fluorescent, relatively thermostable lysochrome (fat-soluble dye) diazo dye used for staining of neutral triglycerides and lipids on frozen sections and some lipoproteins on paraffin sections. It has the appearance of a dark brown to black powder with maximum absorption at 596–605 nm and melting point 120–124 °C. It stains blue-black.

Solvent Black 3
Names
IUPAC name
(2,2-dimethyl-1,3-dihydroperimidin-6-yl)-(4-phenylazo-1-naphthyl)diazene
Other names
Sudan Black; Fat Black HB; Solvent Black 3; C.I. 26150
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.021.898
MeSH Sudan+Black+B
UNII
  • InChI=1S/C29H24N6/c1-29(2)30-26-14-8-13-22-25(17-18-27(31-29)28(22)26)35-34-24-16-15-23(20-11-6-7-12-21(20)24)33-32-19-9-4-3-5-10-19/h3-18,30-31H,1-2H3/b33-32+,35-34+ checkY
    Key: YCUVUDODLRLVIC-VPHDGDOJSA-N checkY
  • InChI=1/C29H24N6/c1-29(2)30-26-14-8-13-22-25(17-18-27(31-29)28(22)26)35-34-24-16-15-23(20-11-6-7-12-21(20)24)33-32-19-9-4-3-5-10-19/h3-18,30-31H,1-2H3/b33-32+,35-34+
    Key: YCUVUDODLRLVIC-VPHDGDOJBF
  • N(=N/c5c1c(cccc1)c(/N=N/c4c2cccc3NC(Nc(c23)cc4)(C)C)cc5)\c6ccccc6
Properties
C29H24N6
Molar mass 456.54 g/mol
Melting point 120 to 124 °C (248 to 255 °F; 393 to 397 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Applications

Solvent Black 3 is used for a wide variety of commercial applications.

In the laboratory, Solvent Black 3 is used for Sudan staining. Similar dyes include Oil Red O, Sudan III, and Sudan IV. It can be used to stain some other materials than the other Sudan dyes, as it is not so specific to lipids. It is used in fingerprint enhancement. It is useful for detecting fats that are contaminated with oil and grease. In differentiating haematological disorders, it will stain myeloblasts but not lymphoblasts.

It was introduced by Lison and Dagnelie in 1935.

Production and composition

Sudan Black is formed by coupling of diazotized 4-phenylazo-1-naphthylamine with 2,3-dihydro-2,2-dimethyl-1H-perimidine.[2] Therefore, the main product expected was 2,3-dihydro-2,2dimethyl-6-[(4-phenylazo-1-naphthalenyl)-azo]-1H-perimidine. However the dye resulting from the above reaction product actually contains many, up to 42 colored and colorless by-products that can be fractionated. The two major products were blue in color confirmed by various chromatographic (TLC and column etc.) separation and spectroscopic (IR, NMR, Mass) identification were named SBB-I & SBB-II (Rf values of 0.49 and 0.19 (chloroform/benzene 1:1, SiO2) in thin Layer Chromatography).[3] The above described product indeed turned out to be SSB-II which comprises up to 60% of the mixture, and the SBB-I was 2,3-dihydro-2,2-dimethyl-4-[(4-phenylazo-1-naphthalenyl)-azo]-1H-perimidine.

References
  1. Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; et al. (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245.
  2. Pfüller, U.; Franz, H.; Preiss, A. (1977). "Histochemistry. 1977 Dec 7;54(3):237-50. Sudan Black B: chemical structure and histochemistry of the blue main components. Pfüller U, Franz H, Preiss A". Histochemistry. 54 (3): 237–250. doi:10.1007/BF00492246. PMID 75201. S2CID 2839405.
  3. Lansink, A. G. W. (1968). "Thin layer chrornatography and histochemistry of Sudan Black B". Histochemie. 16 (1): 68–84. doi:10.1007/BF00306212. PMID 5717700. S2CID 41983162.
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