3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,7S,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]-2-hydroxypropane-1-sulfonate

• ChemBase ID: 105472
• Molecular Formular: C32H58N2O8S
• Molecular Mass: 630.87652
• Monoisotopic Mass: 630.39138783
• SMILES: [O-]S(=O)(=O)CC(O)C[N+](C)(C)CCCNC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@@H]([C@@]4([C@@H](C[C@H](O)CC4)C[C@H]3O)C)C[C@H](O)[C@]12C
• Canonical SMILES: OC(CS(=O)(=O)[O-])C[N+](CCCNC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@H](O)C[C@H]2[C@]1(C)CC[C@H](C2)O)C)(C)C
• InChI: InChI=1S/C32H58N2O8S/c1-20(7-10-29(39)33-13-6-14-34(4,5)18-23(36)19-43(40,41)42)24-8-9-25-30-26(17-28(38)32(24,25)3)31(2)12-11-22(35)15-21(31)16-27(30)37/h20-28,30,35-38H,6-19H2,1-5H3,(H-,33,39,40,41,42)/t20-,21+,22-,23?,24-,25+,26+,27-,28+,30+,31+,32-/m1/s1
• InChIKey: GUQQBLRVXOUDTN-XOHPMCGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,7S,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]-2-hydroxypropane-1-sulfonate; 3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanamido]propyl})azaniumyl]-2-hydroxypropane-1-sulfonate
• IUPAC Traditional name: 3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,7S,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]-2-hydroxypropane-1-sulfonate; 3-[dimethyl({3-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanamido]propyl})ammonio]-2-hydroxypropane-1-sulfonate
• Synonyms: CHAPSO; 3-[(3-Cholamidopropyl)-dimethyl-ammonio]-2-hydroxy-1-propane sulfonate; CHAPSO; 3-([3-Cholamidopropyl]dimethylammonio)-2-hydroxy-1-propanesulfonate; 3-[(3-胆胺丙基)二甲基氨基]-2-羟基-1-丙磺酸内盐

Database IDs

• CAS Number: 82473-24-3
• MDL Number: MFCD00081079
• Beilstein Number: 5842642
• PubChem SID: 24892634; 162092554; 24892713
• PubChem CID: 122145

CALCULATED PROPERTIES

• Acid pKa: -1.0405831
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.7709516
• LogD (pH = 7.4): -1.7709491
• Log P: -2.5632248
• Molar Refractivity: 175.8334 cm^3
• Polarizability: 66.478775 Å^3
• Polar Surface Area: 167.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 M, clear, colorless; H2O: soluble10 mg/mL at 20 °C, clear, colorless
• Melting Point: 184-186 °C(lit.); 184-186°C
• Optical Rotation: [α]20/D +19°, c = 2 in H2O
• Critical Micelle Concentration: 8 mM (micellar weight =9960); 8 mM(20-25°C)
• Conductivity: <50 μmho per cm at 24 °C (0.5 M aqueous solution); ≤100 μmho per cm at 24 °C (0.5 M aqueous solution)
• Aggregation Number of Micelle: 11
• Transition Temperature: cloud point 90 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• 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: 2-8°C

Product Information

• Purity: ≥90.0% (TLC); ≥98%; 95%
• Suitability: suitable for electrophoresis
• Ignition Residue: ≤0.05%; ≤0.1%
• Description: zwitterionic
• Impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Ca: ≤200 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%; Mg: ≤0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤0.01%; 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%; sulfate (SO42-): ≤0.05%
• Mol. Weight: micellar avg mol wt 7000
• Empirical Formula (Hill Notation): C32H58N2O8S

DETAILS

MP Biomedicals - 02190320

A nondenaturing zwitterionic detergent for solubilizing proteins. It has a more polar head group than CHAPS, giving it greater solubility. CHAPSO has a high Cmc (8mM) and does not denature membrane-bound proteins. It can solubilize the opiate receptor in a state exhibiting reversible binding of opiates.

Sigma Aldrich - C9551

Application
具有类似于 CHAPS 特性的非变性两性离子洗涤剂，然而由于具有更强极性的头部基团而更易溶解。适用于内在膜蛋白的增溶。

Sigma Aldrich - C3649

Application
具有类似于 CHAPS 特性的非变性两性离子洗涤剂，然而由于具有更强极性的头部基团而更易溶解。适用于内在膜蛋白的增溶。

Sigma Aldrich - C4695

Application
具有类似于 CHAPS 特性的非变性两性离子洗涤剂，然而由于具有更强极性的头部基团而更易溶解。适用于内在膜蛋白的增溶。

Sigma Aldrich - 374237

Application
A nondenaturing zwitterionic detergent with characteristics similar to CHAPS, although it is more soluble due to a more polar head group. Useful for the solubilization of integral membrane proteins.

Sigma Aldrich - 26675

Application
A nondenaturing zwitterionic detergent with characteristics similar to CHAPS, although it is more soluble due to a more polar head group. Useful for the solubilization of integral membrane proteins.
Other Notes
Zwitterionic detergent that does not denature membrane-bound proteins. ATPase from the plasma membrane of Beta vulgaris1

REFERENCES

• W.F. Simonds, et al., Proc. Nat'l. Acad. Sci. USA , 77 : 4-623 (1980).