N-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide

• ChemBase ID: 134131
• Molecular Formular: C17H25N3O2S
• Molecular Mass: 335.4643
• Monoisotopic Mass: 335.16674806
• SMILES: CN(C)c1cccc2c1cccc2S(=O)(=O)NCCCCCN
• Canonical SMILES: NCCCCCNS(=O)(=O)c1cccc2c1cccc2N(C)C
• InChI: InChI=1S/C17H25N3O2S/c1-20(2)16-10-6-9-15-14(16)8-7-11-17(15)23(21,22)19-13-5-3-4-12-18/h6-11,19H,3-5,12-13,18H2,1-2H3
• InChIKey: MLEBFEHOJICQQS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• IUPAC Traditional name: N-(5-aminopentyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• Synonyms: N-(5-Amino-pentyl)-5-di-methyl-amino-naphtha-lene-1-sulfon-amide; N-(Dimethyl-amino-naphtha-lene-sulfonyl)-1,5-pentane-diamine; Monodansyl cadaverine; Dansylcadaverine; n-(5-aminopentyl)-5-(dimethylamino)Naphthalene-1-sulphonamide

Database IDs

• CAS Number: 10121-91-2
• EC Number: 233-326-9
• MDL Number: MFCD00042704
• Beilstein Number: 2951070
• PubChem SID: 162228408; 24858361; 24893805
• PubChem CID: 4247

CALCULATED PROPERTIES

• Acid pKa: 9.734659
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.9510264
• LogD (pH = 7.4): -0.41502967
• Log P: 1.5097646
• Molar Refractivity: 96.0522 cm^3
• Polarizability: 38.67468 Å^3
• Polar Surface Area: 75.43 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Do you have solubility information on this product that you would like to share?
• Melting Point: 137-140 °C
• Fluorescence: λex 335 nm; λem 518 nm in methanol; λex 338 nm; λem 500 nm (Reaction product)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 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: ≥97% (TLC); ≥99.0% (HPLC); 97%
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C17H25N3O2S

DETAILS

Sigma Aldrich - D4008

Frequently Asked Questions
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Application
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In methanol, dansylcadaverine has a reported λex of 335 nm and λem of 512 nm.
Biochem/physiol Actions
The autofluorescent dye dansylcadaverine, or monodansylcadaverine (MDC), is commonly used to monitor autophagy. MDC preferentially accumulates in autophagic vacuoles due to a combination of ion trapping and specific interactions with membrane lipids.
Other Notes
Solubility of dansylcadaverine is tested in methanol (10 mg/mL). It has also been reported that dansylcadaverine is soluble in DMSO and acetic acid.

Sigma Aldrich - 30432

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Do you have application information on this product that you would like to share?
Biochem/physiol Actions
Inhibitor of the fibrin-stabilizing fator;1 Inhibitor of epidermal growth factor (EGF) internalization;2 Fluorescent substrate for the assay of transamidating enzymes.3,4
The autofluorescent dye dansylcadaverine, or monodansylcadaverine (MDC), is commonly used to monitor autophagy. MDC preferentially accumulates in autophagic vacuoles due to a combination of ion trapping and specific interactions with membrane lipids.
Other Notes
Solubility of dansylcadaverine is tested in methanol (10 mg/mL). It has also been reported that dansylcadaverine is soluble in DMSO and acetic acid.