Basic information
- Standard SMILES
Cc1c(CC(=O)O)c(=O)oc2cc(N)ccc12- InChIKey
QEQDLKUMPUDNPG-UHFFFAOYSA-N- Molecular formula
- C12H11NO4
- Average molar mass
- 233.22 g/mol
- Monoisotopic mass
- 233.06880783
Names & identifiers
- Preferred name
- 7-Amino-4-methylcoumarin-3-acetic acid
- IUPAC
- 2-(7-amino-4-methyl-2-oxochromen-3-yl)acetic acid
- English name
- 7-Amino-4-methyl-3-coumarinylacetic acid
- Molecular formula
- C12H11NO4
- Molecular weight
- 233.22
Names & synonyms
106562-32-77-Amino-4-methylcoumarin-3-acetic acid7-Amino-4-methyl-3-coumarinylacetic acidDTXSID201476487-AMCA compoundRefChem:105782DTXCID7070139635-163-27-Amca2-(7-Amino-4-methyl-2-oxo-2H-chromen-3-yl)acetic acid2-(7-amino-4-methyl-2-oxochromen-3-yl)acetic acidAMCA-H
Show more names
AMCA blueAMCA (coumarin)AMCA Free Acid (Blue)AMCA acid *CAS#: 106562-32-7*AMINO-METHYL-COUMARINACETICACID7-Amino-4-methylcoumarin-3-aceticAcid>7-Amino-4-methyl-3-coumarinylacetic acid
MFCD000810517-Amino-4-methyl-3-coumarinylacetic acid(AMCA)7-Amino-4-methylcoumarin-3-acetateSCHEMBL722252H-1-Benzopyran-3-acetic acid, 7-amino-4-methyl-2-oxo-AMCA acid2H-1-Benzopyran-3-acetic acidAMCA carboxylic acid
Database identifiers
- CAS
106562-32-7- PubChem CID
- 129367
- DTXSID
DTXSID20147648- EC Number
- 635-163-2
- Nikkaji
- J548.222D
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 89.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 388
Experimental & physicochemical properties
Chemical ClassesDyes -> Coumarin Dyes
Physical DescriptionLight brown powder; [Sigma-Aldrich MSDS]
Physicochemical properties
- Boiling point
- 512.2 · 512.2±50.0 °C(Predicted)
- Density
- 1.391 · 1.391±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMF: soluble
- form
- powder to crystal
- pka
- 3.8 · 3.80±0.10(Predicted)
- color
- Light yellow to Brown
- Appearance
- Solid
- λmax
- 344 nm · 344nm(Buffer)(lit.)
- BRN
- 7927205 · 7927205
- InChI
- InChI=1S/C12H11NO4/c1-6-8-3-2-7(13)4-10(8)17-12(16)9(6)5-11(14)15/h2-4H,5,13H2,1H3,(H,14,15)
- InChIKey
- QEQDLKUMPUDNPG-UHFFFAOYSA-N
- SMILES
- C1(=O)OC2=CC(N)=CC=C2C(C)=C1CC(O)=O
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 32 · NA.32
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- HS Code
- 29322090 · 29322090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): 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 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryAn irritant; [Sigma-Aldrich MSDS] See Coumarin 120.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29322090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionAMCA is fluorescent protein labeling agent. It contains an N-hydroxysuccinimide ester that reacts with lysine residues to form photostable amide links. Upon activation with UV light, AMCA displays emission maxima of 400-460 nm. It has commonly been used in multiplex immunophenotyping applications.
Uses7-AMINO-4-METHYL-3-COUMARINYLACETIC ACID is a blue fluorescent dye. Its desirable properties include a relatively large Stoke's shift and resistance to photobleaching. 7-AMINO-4-METHYL-3-COUMARINYLACETIC ACID is used as contrasting probes for double and triple labeling in im
UsesNon-Activated, Amine-Reactive, fluorescent probe
Suppliers50 total
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Related reactions
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