Isopropyl (5Z)-7-[(3R)-3-hydroxy-5-oxo-1-cyclopenten-1-yl]-5-heptenoate
[CAS 876953-80-9]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Isopropyl (5Z)-7-[(3R)-3-hydroxy-5-oxo-1-cyclopenten-1-yl]-5-heptenoate
• Synonyms: propan-2-yl (5Z)-7-[(3R)-3-hydroxy-5-oxocyclopent-1-en-1-yl]hept-5-enoate
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33
• CAS Registry Number: 876953-80-9
• SMILES: CC(C)OC(=O)CCC/C=CCC1=C[C@H](O)CC1=O

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 412.2±45.0 °C 760 mmHg (Calc.)^*
• Flash point: 148.0±22.2 °C (Calc.)^*
• Index of refraction: 1.515 (Calc.)^*

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

Discovery and Applications

Isopropyl (5Z)-7-[(3R)-3-hydroxy-5-oxo-1-cyclopenten-1-yl]-5-heptenoate is a structurally complex ester containing a cyclopentenone-derived ring system linked to a conjugated unsaturated heptenoate chain. The molecule features multiple functional groups, including an ester linkage, an internal alkene with defined Z-configuration, a cyclopentenone core, and a secondary alcohol. The presence of stereochemical descriptors indicates that the compound is a single stereoisomer within a defined chiral framework.

Compounds of this general structural class are typically associated with oxygenated cyclopentanoid derivatives, which are widely encountered in natural products chemistry, particularly among lipid-derived signaling molecules. Cyclopentenone-containing structures are commonly formed in biological systems through oxidative transformations of polyunsaturated fatty acid precursors. These transformations generate reactive intermediates with electrophilic carbonyl groups that can participate in further biochemical reactions.

The isopropyl ester moiety indicates derivatization of a corresponding carboxylic acid. Esterification is a standard transformation in organic chemistry used to modify the physical properties of carboxylic acids, often improving lipophilicity and volatility. Isopropyl esters are frequently used in synthetic chemistry as protecting or prodrug-like groups, depending on the context of application.

The heptenoate chain contains a carbon–carbon double bond with defined (5Z) stereochemistry, indicating a cis-configuration at the alkene. Geometric isomerism in unsaturated fatty acid derivatives plays an important role in determining molecular conformation and reactivity. Cis-configured double bonds introduce bends in hydrocarbon chains, which can significantly influence molecular packing and interaction with biological targets.

The cyclopentenone fragment includes a five-membered ring bearing both a ketone group and a hydroxyl substituent. Cyclopentenones are chemically significant due to the presence of an α,β-unsaturated carbonyl system, which can act as an electrophilic Michael acceptor. Such systems are known to react with nucleophiles under physiological or synthetic conditions, making them reactive intermediates in both chemical synthesis and biological contexts.

The stereochemical designation (3R) at the hydroxyl-bearing carbon indicates a specific three-dimensional arrangement, which is important in determining the compound’s conformational behavior and potential interactions. Stereochemistry is particularly relevant in cyclopentane and cyclopentenone systems, where ring strain and substituent orientation can strongly influence reactivity.

Molecules containing cyclopentenone motifs are often studied in the context of lipid-derived signaling chemistry. Naturally occurring cyclopentenone prostaglandins, for example, are known to arise from oxidative metabolism of arachidonic acid and exhibit electrophilic properties that enable them to modify proteins through covalent interactions with nucleophilic amino acid residues. While the specific compound described here is not necessarily a known endogenous metabolite, its structural features are consistent with intermediates or analogues in related chemical systems.

From a physicochemical perspective, isopropyl (5Z)-7-[(3R)-3-hydroxy-5-oxo-1-cyclopenten-1-yl]-5-heptenoate is expected to exhibit moderate lipophilicity due to its extended hydrocarbon framework, balanced by polar functional groups including an ester, hydroxyl group, and ketone. This combination of hydrophobic and polar features contributes to amphiphilic behavior, which is common in bioactive lipid-like molecules.

The compound’s conjugated unsaturated systems, including the cyclopentenone and the heptenoate double bond, may influence its chemical stability and reactivity. Conjugation with carbonyl groups can stabilize certain electronic configurations while also enabling participation in addition and oxidation reactions. Such features are often exploited in synthetic organic chemistry for selective functionalization.

Overall, isopropyl (5Z)-7-[(3R)-3-hydroxy-5-oxo-1-cyclopenten-1-yl]-5-heptenoate is a multifunctional oxygenated cyclopentanoid ester featuring stereochemically defined centers, conjugated unsaturation, and reactive carbonyl functionality. Its significance lies in its structural relationship to lipid-derived cyclopentenone systems and its potential relevance as a synthetic intermediate in studies of complex oxygenated natural product analogues and bioactive small molecules.