Name | (3beta,9beta,14beta)-cholest-5-ene-3,25-diol |
Synonyms | 25-HYDROXYCHOLESTEROL 5-cholestene-3β,25-diol 5-CHOLESTENE-3BETA,25-DIOL 5-CHOLESTEN-3-BETA, 25-DIOL 3BETA,25-DIHYDROXY-5-CHOLESTENE Cholest-5-ene-3,25-diol, (3.beta.)- 25-Hydroxycholesterol (not deuterated) (3beta,9beta,14beta)-cholest-5-ene-3,25-diol (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
CAS | 2140-46-7 |
InChI | InChI=1/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23-,24-,26+,27-/m1/s1 |
InChIKey | INBGSXNNRGWLJU-ZHHJOTBYSA-N |
Molecular Formula | C27H46O2 |
Molar Mass | 402.65 |
Density | 1.03±0.1 g/cm3(Predicted) |
Melting Point | 177-179 °C |
Boling Point | 513.1±23.0 °C(Predicted) |
Flash Point | 213.5°C |
Solubility | chloroform: 50mg/mL, clear, colorless to slightly yellow |
Vapor Presure | 1.13E-12mmHg at 25°C |
Appearance | solid |
Color | White or pale yellow |
Merck | 13,4846 |
BRN | 3161259 |
pKa | 15.03±0.70(Predicted) |
Storage Condition | -20°C |
Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
Refractive Index | 1.538 |
In vitro study | The synthesis of 25-hydroxycholesterol is catalyzed by the enzyme cholesterol 25-hydroxylase, which uses cholesterol and molecular oxygen as substrates and NADPH as a cofactor. 25-hydroxycholesterol is a potent bioactive lipid in the innate and adaptive immune systems. |
Hazard Symbols | Xn - Harmful |
Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. R48 - Danger of serious damage to health by prolonged exposure |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
WGK Germany | 3 |
HS Code | 29062990 |
Biological activity | 25-Hydroxycholesterol is a metabolite of cholesterol, produced and secreted by macrophages in response to Toll-like receptor (TLR) activation. 25-Hydroxycholesterol effectively and selectively inhibits IgA production by B cells with an EC50 of about 65 nM. |