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206865

Sigma-Aldrich

Primuline

Dye content 50 %

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Synonym(s):
Direct Yellow 59, Primuline Yellow
Empirical Formula (Hill Notation):
C21H14N3NaO3S3
CAS Number:
8064-60-6
Molecular Weight:
475.54
Colour Index Number:
49000
MDL number:
MFCD00005798
UNSPSC Code:
12171500
PubChem Substance ID:
24852417
NACRES:
NA.47

form

powder or crystals

Quality Level

100

composition

Dye content, 50%

mp

>300 °C

λmax

229 nm (2nd)
340-355 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

[Na+].Cc1ccc2nc(sc2c1S([O-])(=O)=O)-c3ccc4nc(sc4c3)-c5ccc(N)cc5

InChI

1S/C21H15N3O3S3.Na/c1-11-2-8-16-18(19(11)30(25,26)27)29-21(24-16)13-5-9-15-17(10-13)28-20(23-15)12-3-6-14(22)7-4-12;/h2-10H,22H2,1H3,(H,25,26,27);/q;+1/p-1

InChI key

RSRNHSYYBLEMOI-UHFFFAOYSA-M

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Application

Primuline has been used as a reagent in the preparation of lipids for chloroplast lipid membrane. It has been used as a dye in preparative thin-layer chromatography (TLC).

Biochem/physiol Actions

Primuline, also known as direct yellow 59 or primuline yellow, is considered to be a more sensitive and non-destructive dye for lipids. It is widely used as a fluorescent dye in preparative thin-layer chromatography (TLC). Primuline is suitable for vital staining. It is used as a fluorochrome in plant tissues. Primuline is also used to stain pollen grains and lignified cell walls. In addition, it also helps in segregating intact and broken starch grains. At pH 8, primuline acts as a fluorochrome for mast cells.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J I Morrell et al.
Science (New York, N.Y.), 217(4566), 1273-1276 (1982-09-24)
A method combining steroid autoradiography and fluorescent dye retrograde neuroanatomical tracing has been devised. This method makes it possible to demonstrate that some estrogen-concentrating cells in the ventrolateral subdivision of the ventromedial nucleus of the rat hypothalamus are neurons that
[Dopamine-containing neurons retrogradely labeled with primuline--a source of descending supraspinal fibers in the rat brain].
F N Serkov et al.
Doklady Akademii nauk SSSR, 292(6), 1506-1509 (1987-01-01)
SEQUENTIAL SYNTHESIS AND METHYLATION OF
PHOSPHATIDYLETHANOLAMINE PROMOTES LIPID DROPLET BIOSYNTHESIS
AND STABILITY IN TISSUE CULTURE AND IN VIVO.
Horl G
The Journal of Biological Chemistry (2011)
T Taki et al.
Analytical biochemistry, 223(2), 232-238 (1994-12-01)
A new and simple method for purifying glycosphingolipids and phospholipids by using "TLC blotting" was established. Glycosphingolipids separated by two-dimensional thin-layer chromatography (TLC) were made visible with primuline reagent, and then bands were marked with a drawing colored pencil. The
J H Duffus et al.
Stain technology, 59(2), 79-82 (1984-03-01)
Treatment of cells and purified cell walls of the fission yeast Schizosaccharomyces pombe with primuline reveals the septum as a bright fluorescent band. When polysaccharides containing (1----3)-beta-, (1----6)-beta- or (1----3)-alpha-glucosidic linkages are treated with primuline, only those molecules containing chains
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