4-[[17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxo-butanoic acid
CHOLESTERYL HYDROGEN SUCCINATE · cholesterylsuccinate · Cholesterol Succinate · Cholesteryl hemisuccite · CHOLESTERYL HEMISUCCINATE · MONO-CHOLESTERYL-SUCCINATE · CHOLESTEROL HYDROGEN SUCCINATE · 5-CHOLESTEN-3β-OL HEMISUCCINATE
![4-[[17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxo-butanoic acid molecular structure](/img/chemical/500055.png)
Identifiers & Physical Properties
| CAS No. | 1510-21-0 |
|---|---|
| Molecular formula | C31H50O4 |
| Average molar mass | 486.7 g/mol |
| SMILES | CC(C)CCCC(C)C1CCC2C3CC=C4CC(OC(=O)CCC(=O)O)CCC4(C)C3CCC12C |
| InChIKey | WLNARFZDISHUGS-UHFFFAOYSA-N |
| PubChem CID | 500055 |
Chemical & Physical Properties
| XLogP | 8.5 |
|---|---|
| Topological polar surface area | 63.6 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 10 |
| Heavy atoms | 35 |
| Formal charge | 0 |
| Complexity | 815 |
| Melting point | 178 °C |
| Boiling point | 586.0±43.0 °C(Predicted) |
| Density | 1.06±0.1 g/cm3(Predicted) |
| Refractive index | -34 ° (C=2, CHCl3) |
| Storage conditions | -20°C |
| Solubility | Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated) |
| Physical state | Solid |
| pKa (acidity coefficient) | 4.40±0.17(Predicted) |
| Color | White to Off-White |
| Cosmetics Ingredients Functions | SKIN CONDITIONINGSKIN CONDITIONING - EMOLLIENT |
| InChIKey | WLNARFZDISHUGS-BLYFUZNHSA-N |
| SMILES | [C@@]12([H])CC=C3C[C@@H](OC(=O)CCC(=O)O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])[C@H](C)CCCC(C)C |&1:0,6,17,19,23,25,28,30,r| |
| LogP (partition coefficient) | 10.708 (est) |
| CAS DataBase Reference | 1510-21-0(CAS DataBase Reference) |
| FDA UNII | T3J4KS4201 |
| UNSPSC Code | 12352103 |
| NACRES | NA.25 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| Customs code | 29171900 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
|---|---|
| Water hazard class (WGK) | 3 |
| Customs code | 29171900 |
| Storage class | 11 - Combustible Solids |
Applications & Uses
Description
Cholesteryl hemisuccinate is a cholesterol ester with anticancer activity. It inhibits the growth of murine C1498 myeloid and L1210 lymphocytic leukemia cells when used at concentrations of 50 and 150 μM, respectively. Cholesteryl hemisuccinate acts as an ionizable anionic detergent and is commonly used to stabilize unilamellar vesicles and liposomes. 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.
Uses
Cholesteryl Hemisuccinate is an oxidation product of polyunsaturated fatty acid of cholesterol that alters lysosome structure and functions and induces proinflammatory cytokine production in macrophages.
General Description
Cholesteryl hemisuccinate (CHEMS) is an acidic cholesterol ester.