4-{[19-(3-carboxypropoxy)-9,22-dioxoheptacyclo[13.11.1.12,10.03,8.016,21.023,27.014,28]octacosa-1,3,5,7,10,12,14(28),15(27),16,18,20,23,25-tridecaen-6-yl]oxy}butanoic acid

• ChemBase ID: 154228
• Molecular Formular: C36H26O8
• Molecular Mass: 586.58684
• Monoisotopic Mass: 586.16276779
• SMILES: c1cc2c3c(c1)C(=O)c1cc(ccc1c3c1cccc3c1c2c1ccc(cc1C3=O)OCCCC(=O)O)OCCCC(=O)O
• Canonical SMILES: OC(=O)CCCOc1ccc2c(c1)C(=O)c1c3c2c2cccc4c2c(c3ccc1)c1ccc(cc1C4=O)OCCCC(=O)O
• InChI: InChI=1S/C36H26O8/c37-29(38)9-3-15-43-19-12-14-22-27(17-19)35(41)25-7-1-5-23-31-21-13-11-20(44-16-4-10-30(39)40)18-28(21)36(42)26-8-2-6-24(34(26)31)32(22)33(23)25/h1-2,5-8,11-14,17-18H,3-4,9-10,15-16H2,(H,37,38)(H,39,40)
• InChIKey: XZWIRUDAKQRKFW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[19-(3-carboxypropoxy)-9,22-dioxoheptacyclo[13.11.1.1^2,^1^0.0^3,^8.0^1^6,^2^1.0^2^3,^2^7.0^1^4,^2^8]octacosa-1,3,5,7,10,12,14(28),15(27),16,18,20,23,25-tridecaen-6-yl]oxy}butanoic acid
• IUPAC Traditional name: 4-{[19-(3-carboxypropoxy)-9,22-dioxoheptacyclo[13.11.1.1^2,^1^0.0^3,^8.0^1^6,^2^1.0^2^3,^2^7.0^1^4,^2^8]octacosa-1,3,5,7,10,12,14(28),15(27),16,18,20,23,25-tridecaen-6-yl]oxy}butanoic acid
• Synonyms: 2,10-Bis(3-carboxypropyloxy)dibenzo[a,j]perylene-8,16-dione; 4,4′-[(8,16-Dihydro-8,16-dioxodibenzo[a,j]perylene-2,10-diyl)dioxy]dibutyric acid

Database IDs

• CAS Number: 243670-14-6
• MDL Number: MFCD07370110
• PubChem SID: 162248367; 24883032
• PubChem CID: 9938325

CALCULATED PROPERTIES

• Acid pKa: 3.5844545
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 2.671458
• LogD (pH = 7.4): -0.53122354
• Log P: 5.9108367
• Molar Refractivity: 162.2702 cm^3
• Polarizability: 67.04785 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 231-235 °C

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (CH)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C36H26O8

DETAILS

Sigma Aldrich - 63951

Analysis Note
luminescence: Emax 668 nm (Eex: 620 nm in chloroform)
Other Notes
Highly photostable, NIR fluorescent label with larger Stokes shift than is usual for cyanine dyes and which is maximally excited, (max CHCl3) 620 nm, by He-Ne laser (630 nm) or diode laser (635 nm).1