6-Carboxyfluorescein
Basic information
- CAS
3301-79-9- Standard SMILES
O=C(O)c1ccc2c(c1)C1(OC2=O)c2ccc(O)cc2Oc2cc(O)ccc21- InChIKey
BZTDTCNHAFUJOG-UHFFFAOYSA-N- Molecular formula
- C21H12O7
- Average molar mass
- 376.3 g/mol
- Monoisotopic mass
- 376.05830272
Overview
6-carboxyfluorescein is a monocarboxylic acid. It is functionally related to a fluorescein (lactone form).
Names & identifiers
- Preferred name
- 6-Carboxyfluorescein
- IUPAC
- 3',6'-dihydroxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylic acid
- English name
- 6-Carboxyfluorescein
- Molecular formula
- C21H12O7
- Molecular weight
- 376.32
Names & synonyms
6-Carboxyfluorescein3301-79-96-FAMJHJ853P6SMCHEBI:39073DTXSID6062965Spiro(isobenzofuran-1(3H),9'-(9H)xanthene)-6-carboxylic acid, 3',6'-dihydroxy-3-oxo-Spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acid, 3',6'-dihydroxy-3-oxo-3',6'-Dihydroxy-3-oxospiro(isobenzofuran-1(3H),9'-(9H)xanthene)-6-carboxylic acid3',6'-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acidRefChem:104358DTXCID5038624
Show more names
3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid6-FAM Acid6-FAM, 6-CF6-FAM, FLUOS6-FAM (Green)6-Carboxyfluoroscein
carboxyfluoresceinFLUOS3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-6-carboxylic acidMFCD00036873Spiro[isobenzofur5(6)-carboxy fluorescein3',6'-dihydroxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylic acidFluorescein Impurity 35
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 637
Physicochemical properties
- Melting point
- 300 °C · >300 °C(lit.)
- Boiling point
- 736.4 · 736.4±60.0 °C(Predicted)
- Density
- 1.73 · 1.73±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- DMSO: soluble
- pka
- 3.3 · 3.3, 4.6, 6.4, 7.0(at 25℃)
- form
- Solid
- color
- Yellow to orange
- PH Range
- Weak green ' uorescence (6.0) to strong green ' uourescence (7.2)
- λmax
- 492 nm · 492nm
- BRN
- 54341 · 54341
- Major Application
- 5 and · Diagnosis of hematologic cancer, nongastric diseases, detection of genetically modified wheat, chromosomes, gene expression, nucleic acid, hepatitis A virus, avian influenza virus subtype H5 and H5N1, SARS virus, herpex simplex virus
- Biological Applications
- Diagnosing bladder cancer; evaluating corneal endothelial barrier function; as a substrate for measuring protein kinase activity, methyltransferase activity, phospholipase activity, rhodanese activity,sulfotransferase activity;use in ophthalmology
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (95.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (95.2%)
Safety data
- F
- 10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 3204 90 00
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Uses & manufacturing
General Manufacturing InformationSpiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acid, 3',6'-dihydroxy-3-oxo-: ACTIVE
Applications
Uses6-Carboxyfluorescein (6-FAM) is derivative of fluorescein giving stable derivative upon conjugation with biopolymers.It has been used to check the plasma membrane integrity in sperm cells. The single isomer, 6-FAM, contains a carboxylic acid that can be used to react with primary amines via carbodiimide activation of the carboxylic acid. Commercially available FAM is a mixture of two isomers, 5-FAM and 6-FAM, and the correct name is 5(6)-carboxyfluorescein.
Preparation methods
Preparation1,2,4-Benzenetricarboxylic anhydride (also called 4- carboxyphthalic anhydride, 25.0 g, 0.13 mol) was added to a solution of 1,3-dihydroxybenzene (also called resorcinol, 28.6 g, 0.26 mol) in methane sulfonic acid (1M). An air condenser was attached to the flask and the reaction was heated at 85 oC in an open vessel for 24 h. After cooling to room temperature, the reaction mixture was poured into 7 volumes of ice/water. An orange-yellow precipitate formed; this was collected by filtration and dried in an oven at 200 oC. This residue was recrystallized two times from methanol/hexane to give 1.0 g of 6- carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes. The mother liquors from this procedure were collected, the solvent was removed in vacuo, and the residues were recrystallized two times from ethanol/hexanes to give 3.2 g of 5-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from EtOH/hexanes. Finally, the mother liquors from this experiment were combined, evaporated to dryness, and recrystallized two times from methanol/hexanes to give another 3.0 g of 6-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes, making a total yield of 4.0 g, 40 %. Careful dropwise addition of conc. HCl(aq) to solutions of these methanesulfonic esters preferentially crystallizes from EtOH/hexanes and preferentially crystallizes from MeOH/hexanes in 4M sodium hydroxide gave 5-carboxyfluorescein and 6-carboxyfluorescein, respectively in near quantitative yield.
Related reactions
33 records
Compound notes
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