bis(7-(dimethylamino)-N,N,1,9-tetramethyl-3H-phenothiazin-3-iminium) dichlorozinc dichloride

• ChemBase ID: 158737
• Molecular Formular: C36H44Cl4N6S2Zn
• Molecular Mass: 832.09676
• Monoisotopic Mass: 828.11144016
• SMILES: Cc1cc(cc2c1nc1c(cc(=[N+](C)C)cc1s2)C)N(C)C.Cc1cc(cc2c1nc1c(cc(=[N+](C)C)cc1s2)C)N(C)C.[Cl-].[Cl-].Cl[Zn]Cl
• Canonical SMILES: CN(c1cc(C)c2c(c1)sc1c(n2)c(C)cc(=[N+](C)C)c1)C.CN(c1cc(C)c2c(c1)sc1c(n2)c(C)cc(=[N+](C)C)c1)C.Cl[Zn]Cl.[Cl-].[Cl-]
• InChI: InChI=1S/2C18H22N3S.4ClH.Zn/c2*1-11-7-13(20(3)4)9-15-17(11)19-18-12(2)8-14(21(5)6)10-16(18)22-15;;;;;/h2*7-10H,1-6H3;4*1H;/q2*+1;;;;;+2/p-4
• InChIKey: MKLBAKXCEQNMBC-UHFFFAOYSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(7-(dimethylamino)-N,N,1,9-tetramethyl-3H-phenothiazin-3-iminium) dichlorozinc dichloride
• IUPAC Traditional name: bis(7-(dimethylamino)-N,N,1,9-tetramethylphenothiazin-3-iminium) zinc chloride dichloride
• Synonyms: DMMB; Taylor’s Blue; 1,9-Dimethyl-Methylene Blue zinc chloride double salt

Database IDs

• CAS Number: 931418-92-7
• MDL Number: MFCD19686959
• PubChem SID: 24860900; 162252873
• PubChem CID: 71312674

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.28577662
• LogD (pH = 7.4): 0.2891531
• Log P: 0.2891963
• Molar Refractivity: 113.2793 cm^3
• Polarizability: 36.34885 Å^3
• Polar Surface Area: 18.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 250 °C (dec.)(lit.)
• Absorption Wavelength: λmax 649 nm

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Compostion: Dye content, 80%
• Impurities: <20% water
• Empirical Formula (Hill Notation): C18H22ClN3S · 0.5ZnCl2

DETAILS

Sigma Aldrich - 341088

Packaging
1 g in glass bottle
Application
DMMB is a cationic dye that specifically binds to sulfated glycosaminoglycans (sGAG) with an absorbance at ~525 nm.1,2 It has been used to quantitate glycosaminoglyans such as chondroitin sulfate, keratin sulfate, and heparan sulfate and sGAG chains in proteoglycans.3,4 One limitation to this method The sGAG-DMMB complex is unstable in solution and may precipitate. Precipitation of the complex was shown to improve stability.5