(5Z)-rel-7-[(1R,2R,3R,5S)-2-[(1E,3S)-4-(3-Chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid
[CAS# 40665-93-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives
• Name: (5Z)-rel-7-[(1R,2R,3R,5S)-2-[(1E,3S)-4-(3-Chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid
• Synonyms: SP 8103
• Molecular Formula: C₂₂H₂₉ClO₆
• Molecular Weight: 424.91
• CAS Registry Number: 40665-93-8
• SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@@H](COC2=CC(=CC=C2)Cl)O)C/C=CCCCC(=O)O)O

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 628.0±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 333.6±31.5 °C (Calc.)^*
• Solubility: Practically insoluble (0.032 g/L) (25 °C), Calc.
• Index of refraction: 1.623 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

The compound is more commonly known as Cloprostenol (or the related analogue) and has a molecular formula of C₂₂H₂₉ClO₆, indicating the presence of a chlorophenoxy moiety, multiple hydroxyls on a cyclopentyl ring, and a heptenoic acid side chain. ([ChemicalBook][1]) Cloprostenol is a synthetic analogue of Prostaglandin F₂α (PGF₂α) and acts as a prostaglandin F-type agonist. ([PharmaCompass.com][2]) The IUPAC-style name you provided corresponds very closely to the descriptor “(Z)-7-[(1R,2R,3R,5S)-2-[(1E,3S)-4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid”, which is used for cloprostenol and its salts. ([ChemicalBook][1])

Pharmacologically, cloprostenol is used primarily in veterinary medicine as a luteolytic agent—it induces regression of the corpus luteum via FP prostanoid receptor activation in cattle, especially for estrus synchronization and related reproductive purposes. ([PharmaCompass.com][2]) It binds to the prostaglandin FP receptor (the receptor for PGF₂α) and mimics or enhances the natural prostaglandin’s ability to cause smooth muscle contraction and luteal regression.

In terms of discovery and development, the compound was developed during the broader era of prostaglandin analogues in which modifications to the prostaglandin F₂α backbone (such as shortening the side chain, adding heteroaryl or phenoxy substituents, adjusting double-bond geometry, and introducing hydroxylations) were explored to enhance potency, selectivity, and metabolic stability. The 3-chlorophenoxy substitution, the cyclopentyl di-hydroxylation pattern, and the precise (1R,2R,3R,5S)/(1E,3S) stereochemistry in cloprostenol illustrate such medicinal chemistry efforts. Analytical and supplier data list CAS numbers such as 40665-93-8 and 54276-21-0 for different stereoisomeric forms of cloprostenol. ([ChemSource][3])

As for applications, while human therapeutic use of cloprostenol is limited, its veterinary role is significant. It is used in livestock to manage reproductive cycles, induce luteolysis, and thereby control breeding and estrus timing. The sodium salt (cloprostenol sodium) has been reported with CAS number 55028-72-3 and is commercially available for such uses. ([Watson International Limited][4])

From a chemical standpoint, the compound retains the characteristic cyclopentane core and a heptenoic acid side chain present in PGF₂α analogues, but with a modified ω-chain (the 3-chlorophenoxy substituted butenyl) and a Z-configuration at the 5-enoic acid double bond (Z vs E), which influence receptor binding and biological activity. Supplier listings confirm the exact descriptor “(5Z)-rel-7-[(1R,2R,3R,5S)-2-[(1E,3S)-4-(3-Chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid” as referring to the compound. ([lopmat.com][5])

Because the substance is primarily a veterinary prostaglandin analogue rather than a widely used human therapeutic, literature focusing on human clinical trials is limited. Nonetheless, the design illustrates how prostaglandin-based compounds have been modified for potency, receptor selectivity, and species-specific applications.

In summary, the compound you listed is cloprostenol (or a stereoisomer thereof), a synthetic prostaglandin F₂α analogue with a specific hydroxylated cyclopentyl core and a chlorophenoxy-butenyl side chain, developed for veterinary reproductive control via FP receptor activation.

References

“Synthesis of 16‑(m‑chlorophenoxy)‑17,18,19,20‑tetranor‑prostaglandin F_2α”, published in Yao xue xue bao = Acta Pharmaceutica Sinica (February 1985) (PMID: 4036619).