3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]propyl})azaniumyl]propane-1-sulfonate

• ChemBase ID: 130814
• Molecular Formular: C32H58N2O7S
• Molecular Mass: 614.87712
• Monoisotopic Mass: 614.39647321
• SMILES: C[C@H](CCC(=O)NCCC[N+](C)(C)CCCS(=O)(=O)[O-])[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]1[C@H]2[C@@H](CC2[C@@]1(CC[C@H](C2)O)C)O)O)C
• Canonical SMILES: O[C@@H]1CC[C@]2(C(C1)C[C@H]([C@@H]1[C@@H]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCCC[N+](CCCS(=O)(=O)[O-])(C)C)C)C)O)C
• InChI: InChI=1S/C32H58N2O7S/c1-21(8-11-29(38)33-14-6-15-34(4,5)16-7-17-42(39,40)41)24-9-10-25-30-26(20-28(37)32(24,25)3)31(2)13-12-23(35)18-22(31)19-27(30)36/h21-28,30,35-37H,6-20H2,1-5H3,(H-,33,38,39,40,41)/t21-,22?,23-,24-,25+,26+,27-,28+,30+,31+,32-/m1/s1
• InChIKey: UMCMPZBLKLEWAF-RFCNGIAKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]propyl})azaniumyl]propane-1-sulfonate
• IUPAC Traditional name: 3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]propyl})ammonio]propane-1-sulfonate
• Synonyms: CHAPS; CHAPS hydrate; 3-[(3-Cholamidopropyl)dimethylammonio]-1-propanesulfonate; CHAPS; 3-[(3-Cholamidopropyl)dimethylammonio]-1-propanesulfonate hydrate; CHAPS solution; CHAPS 100 mM solution; 3-[3-(胆酰胺丙基)二甲氨基]丙磺酸 水合物; 3-[(3-胆酰胺丙基)二甲氨基]丙磺酸内盐; CHAPS

Database IDs

• CAS Number: 75621-03-3; 331717-45-4
• MDL Number: MFCD00012116
• PubChem SID: 24892750; 24851886; 24892997; 162225092; 24892560
• PubChem CID: 53229977

CALCULATED PROPERTIES

• Acid pKa: -1.0029829
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.0806569
• LogD (pH = 7.4): -1.0806528
• Log P: -1.8833573
• Molar Refractivity: 174.7363 cm^3
• Polarizability: 65.82985 Å^3
• Polar Surface Area: 146.99 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 M, clear, colorless; H2O: soluble50 mg/mL at 20 °C, clear, colorless
• Melting Point: 157 °C (dec.)(lit.)
• Density: 1.01 g/mL at 20 °C
• Critical Micelle Concentration: 6 mM(20-25°C)
• Aggregation Number of Micelle: 10
• Transition Temperature: cloud point >100 °C

Safety Information

• European Hazard Symbols: Toxic (T); Irritant (Xi)
• German water hazard class: -; 3
• Risk Statements: 36/37/38; 61; 61-36/37/38
• Safety Statements: 26; 53-26-45; 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H360D
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0%; ≥98% (TLC); ≥98.0% (TLC)
• Concentration: 100 mM in H2O
• Suitability: suitable for electrophoresis
• Ignition Residue: ≤0.1%
• Description: zwitterionic
• Impurities: ≤0.001% Phosphorus (P); ≤0.1% Insoluble matter; ≤8% water
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤0.0005%; Cu: ≤5 mg/kg; Fe: ≤0.0005%; Fe: ≤5 mg/kg; K: ≤0.005%; K: ≤50 mg/kg; Mg: ≤0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤0.005%; Na: ≤50 mg/kg; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤5 mg/kg; Zn: ≤0.0005%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤0.05%; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Quality Level: ELITE
• Mol. Weight: micellar avg mol wt 6150
• Empirical Formula (Hill Notation): C32H58N2O7S; C32H58N2O7S · xH2O

DETAILS

Sigma Aldrich - 26680

Application
CHAPS is a nondenaturing zwitterionic detergent for membrane biochemistry.Useful for solubilizing membrane proteins and breaking protein-protein interactions. CHAPS’ small micellar molecular weight (6,150) and high critical micelle concentration (6-10 mM) allow it to be removed from samples by dialysis. It is also suitable for protein solubilization for isoelectric focusing and two-dimensional electrophoresis. CHAPS is commonly used for non-denaturing (without urea) IEF and has been shown to give excellent resolution of some subcellular preparations and plant proteins. Concentrations between 2-4% (w/v) are typically used in an IEF gel.
Other Notes
Zwitterionic detergent for the solubilisation of membrane proteins. Combines the useful properties of both the sulfobetaine-type and the bile salt detergents1,2; As a non-toxic stabilizing agent for growth factors3

Sigma Aldrich - C3023

General description
A solution at 50 mg/ml in water yields a clear-colorless solution. Aqueous solutions of CHAPS can be autoclaved.

Sigma Aldrich - 05-2605

Application
CHAPS is a nondenaturing zwitterionic detergent for membrane biochemistry.Useful for solubilizing membrane proteins and breaking protein-protein interactions. CHAPS’ small micellar molecular weight (6,150) and high critical micelle concentration (6-10 mM) allow it to be removed from samples by dialysis. It is also suitable for protein solubilization for isoelectric focusing and two-dimensional electrophoresis. CHAPS is commonly used for non-denaturing (without urea) IEF and has been shown to give excellent resolution of some subcellular preparations and plant proteins. Concentrations between 2-4% (w/v) are typically used in an IEF gel.
Suitability
for biological purposes