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5-FAM

5-FAM structure

CAS No:
76823-03-5
Formula:
C21H12O7
Chemical Name:
5-FAM
Synonyms:
Spiro[isobenzofuran-1(3H),9′-[9H]xanthene]-5-carboxylic acid,3′,6′-dihydroxy-3-oxo-;3′,6′-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9′-[9H]xanthene]-5-carboxylic acid;5-Carboxyfluorescein;FAM;FAM (dye);FAM 494/520;5-FAM;73: PN: WO2016072662 SEQID: 73 claimed sequence;Flamma 456 Carboxylic acid;Hydroxyfluorescein;3′,6′-Dihydroxy-3-oxospiro[2-benzofuran-1,9′-xanthene]-5-carboxylic acid;3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylic acid;120719-03-1
Categories:
Dyes and Pigments > Pigment

Description

The single isomer, 5-FAM, contains a carboxylic acid that can be used to react with primary amines via carbodiimide activation of the carboxylic acid. Fluorescein is the most common fluorescent derivatization reagent for labeling biomolecules. In addition to its relatively high absorptivity, excellent fluorescence quantum yield, and good water solubility, fluorescein has an excitation maximum that closely matches the 488 nm spectral line of the argon-ion laser.

5-carboxyfluorescein is a monocarboxylic acid. It has a role as a fluorochrome. It derives from a fluorescein (lactone form).

5-FAM Basic Attributes

Molecular Weight：

376.32

Exact Mass：

376.32

EC Number：

276-331-1

UNII：

AB2MM66GSF

DSSTox ID：

DTXSID30227642

HScode：

2932999099

Characteristics

PSA：

113

XLogP3：

2.9

Appearance：

Yellow to orange Solid

Density：

1.7±0.1 g/cm3

Melting Point：

368-372°C

Boiling Point：

725.2°C at 760 mmHg

Flash Point：

266.9±26.4 °C

Refractive Index：

1.816

Water Solubility：

DMF: soluble

Storage Conditions：

Storeat2-8

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

26-39

Marks：

Precautionary statement(s)：

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 5 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4(5)-carboxyfluorescein

5-FAM Use and Manufacturing

Methods of Manufacturing

General procedure: To a solution of To the mixture of NH2-NB-72 (3 mg, 4.90 gmol) and 5-FAM (3.4 mg, 7.40 mhio) in DMF (100 gL) was added (11 mg, 0.11 mmol) at rt and reacted for 1 hr at rt. After the solvent was evaporated using a nitrogen stream, the title compound (Fluorescein-NB-72, 1.4 mg) was separated on S1O2 PLC using 10% MeOH/DCM (v/v). ESI (m/z) 971.9 (NT +1), 487.6 (0638) (M/Z2+2H).To a solution of 12w in THF at room temperature was added 13w, BOP and triethylamine. The reaction was stirred at room temperature for 22 h. The mixture was then filtered through Celite. The filtrate was concentrated under reduced pressure. The crude residue was purified by prep-HPLC to give 14w.

Uses

5-Carboxyfluorescein is a single isomer derivative of 5(6)-carboxyfluorescein that can be used to fluorescently label biomolecules through the interaction of carboxylic acid with primary amines. It demonstrates excitation/emission maxima of 492 and 518 nm, respectively.

Computed Properties

Molecular Weight:376.3
XLogP3:2.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:1
Exact Mass:376.05830272
Monoisotopic Mass:376.05830272
Topological Polar Surface Area:113
Heavy Atom Count:28
Complexity:637
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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