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(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one
1. Basic Information
Name: (+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one
Alias: Travoprost Lactone Diol, Fluprostenol Lactone Diol
CAS No.: 53872-60-9
Molecular Formula: C18H19F3O5
Molecular Weight: 372.34
Category: Chiral fluorinated prostaglandin pharmaceutical intermediate, prostaglandin analogue key building block
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to off-white crystalline solid
- Odor: Odorless chiral polyhydroxy lactone solid
- Solubility: Soluble in methanol, ethanol, DMSO, acetonitrile, ethyl acetate; slightly soluble in methyl tert-butyl ether; insoluble in alkane solvents and pure water
- Melting Behavior: Decomposes on heating without distinct sharp melting point
- Hygroscopy: Slightly hygroscopic under high humidity
- Aqueous Property: Lipophilic chiral lactone; only forms homogeneous solution with polar organic co-solvents
Chemical Properties
- Molecular Structure: Fused cyclopenta[b]furan lactone bicyclic skeleton with multiple chiral hydroxyl groups, E-type carbon-carbon double bond, and meta-trifluoromethyl phenoxy side chain
- Lactone Ring Reactivity: Lactone ring undergoes ring-opening hydrolysis under strong alkaline heating to generate linear prostaglandin diacid derivative
- Hydroxyl Group Activity: Two secondary hydroxyl groups can conduct esterification, silylation and oxidation protection reactions for chiral synthesis
- Thermal Stability: Stable under 2–8 °C cold storage; rapid chiral skeleton degradation and oxidation at room temperature long-term exposure
- Photostability: Extremely sensitive to UV light; illumination triggers double bond oxidation and racemization of chiral centers
- Compatibility: Compatible with anhydrous polar aprotic solvents; incompatible with strong oxidants, concentrated strong alkali, heavy metal ions and acidic heating conditions
3. Main Application Fields
1. Ocular Drug API Intermediate (Core Application)
Key chiral precursor for synthesizing Travoprost and Fluprostenol prostaglandin eye drops; finished drugs reduce intraocular pressure for glaucoma clinical treatment.
2. Pharmaceutical Impurity Reference Standard
HPLC reference substance for impurity detection and quality control during Travoprost bulk drug production lines.
3. Prostaglandin Biochemical Research Reagent
Tool compound for in vitro prostaglandin receptor signaling pathway research, intraocular pressure pharmacology laboratory studies.
4. Quality Specification Table
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to off-white crystalline solid
- Odor: Odorless chiral polyhydroxy lactone solid
- Solubility: Soluble in methanol, ethanol, DMSO, acetonitrile, ethyl acetate; slightly soluble in methyl tert-butyl ether; insoluble in alkane solvents and pure water
- Melting Behavior: Decomposes on heating without distinct sharp melting point
- Hygroscopy: Slightly hygroscopic under high humidity
- Aqueous Property: Lipophilic chiral lactone; only forms homogeneous solution with polar organic co-solvents
Chemical Properties
- Molecular Structure: Fused cyclopenta[b]furan lactone bicyclic skeleton with multiple chiral hydroxyl groups, E-type carbon-carbon double bond, and meta-trifluoromethyl phenoxy side chain
- Lactone Ring Reactivity: Lactone ring undergoes ring-opening hydrolysis under strong alkaline heating to generate linear prostaglandin diacid derivative
- Hydroxyl Group Activity: Two secondary hydroxyl groups can conduct esterification, silylation and oxidation protection reactions for chiral synthesis
- Thermal Stability: Stable under 2–8 °C cold storage; rapid chiral skeleton degradation and oxidation at room temperature long-term exposure
- Photostability: Extremely sensitive to UV light; illumination triggers double bond oxidation and racemization of chiral centers
- Compatibility: Compatible with anhydrous polar aprotic solvents; incompatible with strong oxidants, concentrated strong alkali, heavy metal ions and acidic heating conditions
3. Main Application Fields
1. Ocular Drug API Intermediate (Core Application)
Key chiral precursor for synthesizing Travoprost and Fluprostenol prostaglandin eye drops; finished drugs reduce intraocular pressure for glaucoma clinical treatment.
2. Pharmaceutical Impurity Reference Standard
HPLC reference substance for impurity detection and quality control during Travoprost bulk drug production lines.
3. Prostaglandin Biochemical Research Reagent
Tool compound for in vitro prostaglandin receptor signaling pathway research, intraocular pressure pharmacology laboratory studies.
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 53872-60-9 |
| Molecular Formula | C18H19F3O5 |
| Appearance | Uniform white crystalline solid without colored impurities |
| HPLC Purity | Pharma Intermediate Grade ≥99.0%; Reference Standard ≥99.5% |
| Enantiomeric Excess (ee) | ≥99.0% |
| Water Content (KF) | ≤0.30% |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-purged amber glass vials / vacuum aluminum foil bags |
| Storage Condition | Hermetically sealed dark cold storage at 2–8 °C; strictly protected from light, moisture, oxidants and alkaline reagents |
| Transportation Requirement | Chiral light-sensitive prostaglandin intermediate; cold-chain light-proof fully sealed transport |
| Shelf Life | 24 months under nitrogen-filled frozen cold storage |
Safety Warning
Biologically active irritant fluorinated chiral lactone solid. Dust causes severe irritation to eyes, respiratory tract and skin; long-term skin contact may induce erythema and allergic dermatitis. All handling operations must be carried out inside ventilated chemical fume hoods with dust respirators, chemical-resistant gloves and full-face safety goggles. Mandatory low-temperature light-proof airtight storage to avoid racemization and oxidation activity loss. Waste liquid requires anhydrous solvent recovery and neutralization treatment; solid waste is classified as high-potency pharmaceutical hazardous waste and must be disposed by licensed professional hazardous waste treatment facilities.
