Available from stock

Cholesteryl hemisuccinate

SKU: C0828

Category: API's & Intermediates

Synonyms: 3?-Hydroxy-5-cholestene 3-hemisuccinate, 5-Cholesten-3?-ol 3-hemisuccinate, Cholesteryl hydrogen succinate; 1510-21-0
CAS-Number: C₃₁H₅₀O₄
Molecular Formula: 486.73
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (NMR)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: chloroform (10mg/ml), DMSO, ethanol (both 1mg/ml)
Melting Point: 178-182° C

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: RT
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at RT.

Transportation: Not dangerous goods

Description: Cholesteryl hemisuccinate (CHEMS) is a cholesterol ester. It is formed by esterifying cholesterol with succinic acid. The chemical structure comprises a cholesterol molecule attached to a succinic acid moiety. It possesses both hydrophilic (water-attracting) and hydrophobic (water-repelling) properties, making it useful as a surfactant. CHEMS can form lyotropic liquid crystals, which are important in the formation of liposomes and other nanoparticle drug delivery systems. CHEMS acts as an ionizable anionic detergent and is commonly used to stabilize unilamellar vesicles and liposomes. CHEMS is commonly used in the formulation of liposomes and other lipid-based drug delivery systems. These systems can encapsulate drugs, enhancing their stability, bioavailability, and controlled release. It has also been used as an emulsifying agent in various vesicular drug delivery systems for anticancer drugs, antibiotics, and oligonucleotides and to solubilize various proteins including chemokine receptor 1 as well as erythrocyte ghosts. In addition is used in the study of membrane proteins and the biophysical properties of cell membranes. CHEMS has also been described to have anticancer activity.
Smiles: C[C@@]12[C@]3([H])[C@](CC=C1C[C@H](CC2)OC(CCC(O)=O)=O)([H])[C@@]4([H])[C@](CC3)([C@@](CC4)([H])[C@H](C)CCCC(C)C)C
InChi Key: WLNARFZDISHUGS-MIXBDBMTSA-N
References: (1) J.E. Carroll, et al.; Life Sci. 32, 1573 (1983) , (2) Y.G. Skornick, et al.; Cancer 58, 650 (1986) , (3) M.W. Fariss, et al.; Cancer Res. 54, 3346 (1994) , (4) D. Bach, et al.; Chem. Phys. Lipids 76, 123 (1995) , (5) J.B. Massey; Biochim. Biophys. Acta 1415, 193 (1998) , (6) I.M. Hafez & P.R. Cullis; Biochim. Biophys. Acta 1463, 107 (2000) , (7) S. Simoes, et al.; Adv. Drug Deliv. Rev. 56, 947 (2004) , (8) W.X. Ding, et al.; Int. J. Pharm. 300, 38 (2005) , (9) H. Xu, et al.; Drug Dev. Ind. Pharm. 34, 134 (2008) , (10) S.J. Allen, et al.; Protein Expr. Purif. 66, 73 (2009) , (11) W. Kulig, et al.; J. Mol. Model 20, 2121 (2014) , (12) L. Luo, et al.; Colloids Surf. B Biointerfaces 172, 262 (2018) , (13) H. Shah, et al.; Pharmaceutics 14, 129 (2022)
InChi: InChI=1S/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1

Cholesteryl hemisuccinate (CHEMS) is a cholesterol ester. It is formed by esterifying cholesterol with succinic acid. The chemical structure comprises a cholesterol molecule attached to a succinic acid moiety. It possesses both hydrophilic (water-attracting) and hydrophobic (water-repelling) properties, making it useful as a surfactant. CHEMS can form lyotropic liquid crystals, which are important in the formation of liposomes and other nanoparticle drug delivery systems. CHEMS acts as an ionizable anionic detergent and is commonly used to stabilize unilamellar vesicles and liposomes. CHEMS is commonly used in the formulation of liposomes and other lipid-based drug delivery systems. These systems can encapsulate drugs, enhancing their stability, bioavailability, and controlled release. It has also been used as an emulsifying agent in various vesicular drug delivery systems for anticancer drugs, antibiotics, and oligonucleotides and to solubilize various proteins including chemokine receptor 1 as well as erythrocyte ghosts. In addition is used in the study of membrane proteins and the biophysical properties of cell membranes. CHEMS has also been described to have anticancer activity.

SKU: C0828 Category: API's & Intermediates

Additional information

Additional information

Synonyms	3?-Hydroxy-5-cholestene 3-hemisuccinate, 5-Cholesten-3?-ol 3-hemisuccinate, Cholesteryl hydrogen succinate
Purity	≥98% (NMR)
Appearance	White to off-white powder
CAS-Number	1510-21-0
Molecular Formula	C31H50O4
Molecular Weight	486.73
Identity	1H-NMR
Solvents	chloroform (10mg/ml), DMSO, ethanol (both 1mg/ml)
Melting Point	178-182° C
Smiles	C[C@@]12[C@]3([H])[C@](CC=C1C[C@H](CC2)OC(CCC(O)=O)=O)([H])[C@@]4([H])[C@](CC3)([C@@](CC4)([H])[C@H](C)CCCC(C)C)C
InChi Key	WLNARFZDISHUGS-MIXBDBMTSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	RT
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at RT.
Transportation	Not dangerous goods
References	(1) J.E. Carroll, et al.; Life Sci. 32, 1573 (1983), (2) Y.G. Skornick, et al.; Cancer 58, 650 (1986), (3) M.W. Fariss, et al.; Cancer Res. 54, 3346 (1994), (4) D. Bach, et al.; Chem. Phys. Lipids 76, 123 (1995), (5) J.B. Massey; Biochim. Biophys. Acta 1415, 193 (1998), (6) I.M. Hafez & P.R. Cullis; Biochim. Biophys. Acta 1463, 107 (2000), (7) S. Simoes, et al.; Adv. Drug Deliv. Rev. 56, 947 (2004), (8) W.X. Ding, et al.; Int. J. Pharm. 300, 38 (2005), (9) H. Xu, et al.; Drug Dev. Ind. Pharm. 34, 134 (2008), (10) S.J. Allen, et al.; Protein Expr. Purif. 66, 73 (2009), (11) W. Kulig, et al.; J. Mol. Model 20, 2121 (2014), (12) L. Luo, et al.; Colloids Surf. B Biointerfaces 172, 262 (2018), (13) H. Shah, et al.; Pharmaceutics 14, 129 (2022)
InChi	InChI=1S/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1
Quantity	5 g, 25 g, Bulk