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Ingenol-3-angelate
1. Basic Information
Name: Ingenol-3-angelate
Alias: Ingenol Mebutate, PEP005
CAS No.: 75567-37-2
Molecular Formula: C25H34O6
Molecular Weight: 430.54
Category: Natural tetracyclic diterpenoid ester isolated from Euphorbia peplus
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to pale beige crystalline powder
- Odor: Odorless diterpene solid
- Solubility: Soluble in DMSO, methanol, ethanol, acetone and chloroform; slightly soluble in vegetable oils; insoluble in pure water
- Melting Behavior: No clear melting point, thermal decomposition occurs upon heating
- Predicted Boiling Point: 576.9 ± 50.0 °C
- Hygroscopy: Slightly hygroscopic under high humidity
- Aqueous Property: Highly lipophilic; unable to form homogeneous aqueous solution without organic co-solvents
Chemical Properties
- Molecular Structure: Tetracyclic ingenane scaffold with multiple chiral hydroxyl groups, one ketone group and an angelate ester moiety at the C3 position
- Ester Hydrolysis Profile: Stable under neutral and weakly acidic environments; ester linkage hydrolyzes under heating with strong alkali to produce free ingenol and angelic acid
- Biological Mechanism: Potent selective protein kinase C (PKC) isoform activator; triggers keratinocyte apoptosis and local cutaneous immune response
- Oxidation Susceptibility: Polyhydroxy structure readily oxidizes upon prolonged exposure to air and UV light, leading to gradual browning
- Thermal Stability: Long-term stable at -20 °C; rapid structural degradation at ambient temperature
- Photostability: Extremely light-sensitive; UV irradiation damages chiral skeleton and eliminates pharmacological activity
- Compatibility: Miscible with alcoholic, glycol and oily pharmaceutical excipients; incompatible with strong oxidants, concentrated alkaline reagents and heavy metal ions
3. Main Application Fields
1. Clinical Active Pharmaceutical Ingredient (Core Application)
Active component of topical gel formulation (Picato®) for the treatment of actinic keratosis (precancerous cutaneous lesions) on the face, scalp, trunk and extremities. It eliminates abnormal lesion cells through targeted apoptosis and local inflammatory immune clearance.
2. Anti-Tumor Laboratory Research Reagent
Tool compound for in vitro and in vivo oncology research; used to investigate PKC signaling pathways, tumor cell proliferation and skin tumor pathogenesis.
3. Biochemical Reference Standard
HPLC reference substance for quantitative detection of ingenane diterpenoid derivatives in Euphorbia plant extracts and pharmaceutical finished products.
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 75567-37-2 |
| Molecular Formula | C25H34O6 |
| Appearance | White to pale beige crystalline powder |
| HPLC Purity | Pharma Grade ≥98.0%; Reference Standard ≥99.5% |
| Water Content (KF) | ≤0.30% |
| Optical Purity | Single stereoisomer, no detectable diastereomeric impurities |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-purged amber vacuum aluminum foil bags / amber glass vials |
| Storage Condition | Hermetically sealed storage at -20 °C in dark environment; strictly protected from moisture, light, oxidants and alkaline substances |
| Transportation Requirement | Biologically active light-sensitive diterpenoid; cold-chain light-proof fully sealed transport |
| Shelf Life | 24 months under nitrogen-filled vacuum frozen storage |
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