82473-24-3

Basic information

• Product Name: 3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate
• Synonyms: CHAPSO;3-[(3-CHOLAMIDOPROPYL)DIMETHYLAMMONIO]-2-HYDROXY-1-PROPANESULFONATE;3-[(3-CHOLAMIDOPROPYL)DIMETHYLAMMONIO]-2-HYDROXY-1-PROPANE SULPHONATE;3-((3-cholamidopropyl)dimethylammonio)-2-hydroxy-;CHAPSO 3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate;CHAPSO SIGMAULTRA;CHAPSO ELECTROPHORESIS REAGENT;1-Propanaminium, 2-hydroxy-N,N-dimethyl-3-sulfo-N-3-(3.alpha.,5.beta.,7.alpha.,12.alpha.)-3,7,12-trihydroxy-24-oxocholan-24-ylaminopropyl-, inner salt
• CAS NO: 82473-24-3
• Molecular Formula: C32H58N2O8S
• Molecular Weight: 630.88
• EINECS: 2017-001-1
• Product Categories: detergent
• Mol File: 82473-24-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 184-186 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.0453 (rough estimate)
• Refractive Index: 1.6900 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 10 mg/mL at 20 °C, clear, colorless
• Water Solubility: 10 g/l at 20 °C
• Merck: 13,2052
• BRN: 5842642
• CAS DataBase Reference: 3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate(82473-24-3)
• EPA Substance Registry System: 3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate(82473-24-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 82473-24-3(Hazardous Substances Data)

Usage

Description

3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate, also known as CHAPSO, is a non-denaturing zwitterionic bile salt derivative. It is derived from CHAPS by the addition of a functional hydroxyl group, resulting in a more polar head group and enhanced solubility. CHAPSO is a white crystalline powder and is similar to CHAPS in its zwitterionic detergent properties, but with improved solubility and effectiveness in solubilizing integral membrane proteins.

Uses

Used in Biochemistry Research:
CHAPSO is used as a nondenaturing biological detergent for the solubilization of integral membrane proteins. Its more polar head group compared to CHAPS makes it more soluble and effective in this application.
Used in Bicelle Preparation:
CHAPSO is used in the preparation of bicelles for the reconstitution of membrane proteins, such as the β2-adrenergic receptor. It has been utilized in studies to assess liposome solubilization and reconstitution of transport proteins, as well as in the development of novel bicelle systems for orienting macromolecules over a wide temperature range.
Used in Solid-State Nuclear Magnetic Resonance (NMR) Technique:
CHAPSO has been used in conjunction with dilauroyl phosphatidylcholine (DLPC) in solid-state NMR techniques to study membrane-associated proteins. This mixture aids in the investigation of protein structures and interactions within the membrane environment.

Purification Methods

Dissolve this zwitterionic detergent (~ 60g) in 40% aqueous MeOH and stir it with the mixed-bed ion-exchange resin RG-501 x 8 (100g, Bio-Rad) until the pH of the supernatant is ~ 7. Filter off the resin and evaporate the filtrate to dryness under reduced pressure. Check for homogeneity by TLC on silica gel G in 95% MeOH/5% NH4OH and visualize the spot with iodine vapour (see CHAPS above). [Hjelmeland et al. Anal Biochem 130 72 1983, Matuo et al. Methods Enzymol 198 155 1991.]

InChI:InChI=1/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