(acetyloxy)methyl 3-{3',6'-bis[(acetyloxy)methoxy]-7'-{3-[(acetyloxy)methoxy]-3-oxopropyl}-5-{[(acetyloxy)methoxy]carbonyl}-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-2'-yl}propanoate

• ChemBase ID: 133409
• Molecular Formular: C42H40O21
• Molecular Mass: 880.7544
• Monoisotopic Mass: 880.2062083
• SMILES: CC(=O)OCOc1cc2c(cc1CCC(=O)OCOC(=O)C)C1(c3ccc(cc3C(=O)O1)C(=O)OCOC(=O)C)c1cc(c(cc1O2)OCOC(=O)C)CCC(=O)OCOC(=O)C
• Canonical SMILES: O=C(CCc1cc2c(cc1OCOC(=O)C)Oc1c(C32OC(=O)c2c3ccc(c2)C(=O)OCOC(=O)C)cc(c(c1)OCOC(=O)C)CCC(=O)OCOC(=O)C)OCOC(=O)C
• InChI: InChI=1S/C42H40O21/c1-22(43)52-17-57-34-15-36-32(13-27(34)7-10-38(48)59-19-54-24(3)45)42(31-9-6-29(12-30(31)41(51)63-42)40(50)61-21-56-26(5)47)33-14-28(8-11-39(49)60-20-55-25(4)46)35(16-37(33)62-36)58-18-53-23(2)44/h6,9,12-16H,7-8,10-11,17-21H2,1-5H3
• InChIKey: NTECHUXHORNEGZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (acetyloxy)methyl 3-{3',6'-bis[(acetyloxy)methoxy]-7'-{3-[(acetyloxy)methoxy]-3-oxopropyl}-5-{[(acetyloxy)methoxy]carbonyl}-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-2'-yl}propanoate
• IUPAC Traditional name: (acetyloxy)methyl 3-{3',6'-bis[(acetyloxy)methoxy]-7'-{3-[(acetyloxy)methoxy]-3-oxopropyl}-5-{[(acetyloxy)methoxy]carbonyl}-3-oxospiro[2-benzofuran-1,9'-xanthene]-2'-yl}propanoate
• Synonyms: BCECF-acetoxymethyl; 2′,7′-bis(2-Carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester Mixed isomers; BCECF-AM solution; Spiro(isobenzofuran-1(3H),9′-(9H)xanthene)-2′,7′-dipropanoic acid; 2′,7′-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester

Database IDs

• CAS Number: 117464-70-7
• EC Number: 200-664-3
• MDL Number: MFCD00036969
• PubChem SID: 162227686
• PubChem CID: 53229972

CALCULATED PROPERTIES

• H Acceptors: 11
• H Donor: 0
• LogD (pH = 5.5): 3.9376516
• LogD (pH = 7.4): 3.9376516
• Log P: 3.9376516
• Molar Refractivity: 204.8319 cm^3
• Polarizability: 81.64762 Å^3
• Polar Surface Area: 264.39 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: colorless to yellow
• Flash Point: 185 °F; 85 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1; 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Concentration: 1 mg/mL in DMSO
• Description: Mixture of six isomeric compounds

DETAILS

Sigma Aldrich - C8427

General description
Material is an isomeric mixture of lactones, acetates, and AM esters
Other Notes
Membrane-permeable fluorescent probe for cytoplasmic pH.

Sigma Aldrich - B8806

Biochem/physiol Actions
An intracellular fluorescent pH indicator.
Hydrolyzed to BCECF by cytosolic esterases.
Physical form
Solution in 0.1% BCECF AM Ester and 99.9% DMSO