Chinese name: isotretinoic acid

English name :Isotretinoin

CAS:4759-48-2

EINECS number :225-296-0

Molecular formula :C20H28O2

MDL number :MFCD00079542

Molecular weight :300.44

Appearance: orange-red flake crystal obtained from isopropyl alcohol, melting point 174 ~ 175℃. UV maximum absorption: 354nm(ε39800). Acute toxicity LD50(20 days) in mice, rats (mg/kg) : 904,901 by intraperitoneal injection; 3389 > 4000 oral.

Melting point :172-175 °C(lit.)

Boiling point :381.66°C (rough estimate)

Density :1.0597 (rough estimate)

Refractive index :1.4800 (estimate)

Storage condition :?20°C

Solubility :Practically insoluble in water, soluble in methylene chloride, slightly soluble in ethanol (96 per cent). It is sensitive to air, heat and light,  especially in solution. Carry out all operations as rapidly as possible and avoid exposure to actinic light;  use freshly prepared solutions.

Predicted Acidity coefficient (pKa):4.76±0.33

Form: fine crystalline powder

Color: yellow-orange to orange

Water solubility :insoluble

Maximum wavelength (λmax):354nm(EtOH)(lit.)

Merck: 14522 8

Stability: Stable, but may be sensitive to air and light. Incompatible with strong oxidants.

InChIKey:SHGAZHPCJJPHSC-YCNIQYBTSA-N

use

It is used to treat severe acne

Preparation method

After reacting with ethyl magnesium chloride, β-ionone reacts with triphenylphosphine to form triphenyl ester salt, and then reacts with cyclopentenone derivatives to form isotretinoic acid and its 8Z isomer.

The 8Z isomer was separated and isomerized to isotretinoic acid by palladium nitrate.