Lucifer yellow

Names
Preferred IUPAC name

Dilithium 6-amino-2-(hydrazinecarbonyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5,8-disulfonate

Identifiers

CAS Number

* 77944-88-8 N

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:52104 Y

ChEMBL |

* ChEMBL1650069

ChemSpider |

* 20137740 N

PubChem CID

* 20835957

UNII |

* 9654F8OVKE

CompTox Dashboard (EPA)

* DTXSID70999134

InChI

* InChI=1S/C13H10N4O9S2.2Li/c14-10-5-1-4(27(21,22)23)2-6-9(5)7(3-8(10)28(24,25)26)12(19)17(11(6)18)13(20)16-15;;/h1-3H,14-15H2,(H,16,20)(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2 N

Key: DLBFLQKQABVKGT-UHFFFAOYSA-L N

SMILES

* c1c(cc2c3c1c(c(cc3c(=O)n(c2=O)C(=O)NN)S(=O)(=O)[O-])N)S(=O)(=O)[O-].[Li+].[Li+]

Properties

Chemical formula

| C13H10Li2N4O9S2
Molar mass | 444.24 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

Lucifer yellow is a fluorescent dye used in cell biology.[1] The key property of Lucifer yellow is that it can be readily visualized in both living and fixed cells using a fluorescence microscope. Lucifer yellow was invented by Walter W. Stewart at the National Institutes of Health and patented in 1978.[2]

## Preparations[edit]

For common usage it is compounded with carbohydrazide (CH) and prepared as a lithium salt. The CH group allows it to be covalently linked to surrounding biomolecules during aldehyde fixation.[3]

Other cations such as ammonium or potassium can be used when lithium is undesirable, but the resulting salts are less soluble in water.

Lucifer yellow can also be compounded as a vinyl sulfone, with ethylenediamine, or with cadaverine.[clarification needed]

## References[edit]

1. ^ Hanani, Menachem (January 2012). "Lucifer yellow – an angel rather than the devil". Journal of Cellular and Molecular Medicine. 16 (2): 22–31. doi:10.1111/j.1582-4934.2011.01378.x. PMC 3823090. PMID 21740513.
2. ^ Patent description
3. ^ "Lucifer Yellow CH, Lithium Salt". Molecular Probes. Retrieved 17 March 2014.

## External links[edit]

* Invitrogen's manual for Lucifer yellow
* Molecular structure and spectra of Lucifer yellow CH (lithium salt)

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency