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Sigma-Aldrich

Fluorescein o-acrylate

95%

Synonym(s):

3’-Acryloxyspirobenzo[c]-furan[1,9’]xanthen-3-one, Acryloyloxy fluorescein

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About This Item

Empirical Formula (Hill Notation):
C23H14O6
CAS Number:
193419-86-2
Molecular Weight:
386.35
UNSPSC Code:
12352103
PubChem Substance ID:
24880227
NACRES:
NA.23

Assay

95%

form

solid

mp

231-233 °C (lit.)

λmax

490 nm

storage temp.

2-8°C

SMILES string

Oc1ccc2c(Oc3cc(OC(=O)C=C)ccc3C24OC(=O)c5ccccc45)c1

InChI

1S/C23H14O6/c1-2-21(25)27-14-8-10-18-20(12-14)28-19-11-13(24)7-9-17(19)23(18)16-6-4-3-5-15(16)22(26)29-23/h2-12,24H,1H2

InChI key

VYLDMXSRCVCHNE-UHFFFAOYSA-N

General description

Fluorescein o-acrylate is a fluorescent monomer with high quantum efficiency in aqueous media. Its excitation and emission wavelength are in the range of visible light. It can be copolymerized with a variety of monomers such as acrylic acid, styrene and acrylamide which facilitate the attachment of fluorescein with macromolecules.

Application

Fluorescein o-acrylate can be used in the formation of fluorescent probes for application in bio-imaging. It can also be used in the synthesis of molecularly imprinted polymers (MIPs). It also facilitates the demarcation of different layers in fluorescence microscopy.
Fluorescent monomer

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H319,H335,H411

Hazard Classifications

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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A fluorescein-based probe with high selectivity to cysteine over homocysteine and glutathione
Wang H, et al.
Chemical Communications (Cambridge, England), 48(67), 8341-8343 (2012)
Feifei Wang et al.
Polymers, 11(12) (2019-11-30)
In this study, we established a new fluorescent indicator platform. The responsive element consists of poly(N-isopropylacrylamide) nanospheres that include small percentages of fluorescein and a ligand, anilinodiacetate (phenylIDA). Nanosphere diameters were determined to be in the range from 50 to
Sequential formation of covalently bonded hydrogel multilayers through surface initiated photopolymerization
K?z?lel S, et al.
Biomaterials, 27(8), 1209-1215 (2006)
Synthesis and photophysical behavior of a water-soluble fluorescein-bearing polymer for Fe 3+ ion sensing
Wang B, et al.
Journal of Polymer Research, 15(6), 427-433 (2008)
Benxin Jing et al.
Soft matter, 13(28), 4881-4889 (2017-06-21)
Coacervate complexes that are liquid-liquid separated complex materials are often formed by stoichiometrically mixing oppositely charged polyelectrolytes in salted aqueous solution. Entropy-driven ion pairing, resulting from the release of counterions near polyelectrolytes, has been identified as the primary driving force
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