Cypionic acid

Cypionic acid, also known as cyclopentylpropionic acid, is an aliphatic carboxylic acid with the molecular formula C₈H₁₄O₂. Its salts and esters are known as cypionates or cipionates.

Cypionic acid

Names
Preferred IUPAC name 3-Cyclopentylpropanoic acid
Other names 3-Cyclopentylpropionic acid; 3-Cyclopentanepropionic acid; Cypionate; Cipionate
Identifiers
CAS Number	140-77-2^Y
3D model (JSmol)	Interactive image
ChemSpider	8487
ECHA InfoCard	100.004.940
PubChem CID	8818
UNII	931H8F0JEE^Y
CompTox Dashboard (EPA)	DTXSID4059700
InChI InChI=1S/C8H14O2/c9-8(10)6-5-7-3-1-2-4-7/h7H,1-6H2,(H,9,10) Key: ZRPLANDPDWYOMZ-UHFFFAOYSA-N InChI=1/C8H14O2/c9-8(10)6-5-7-3-1-2-4-7/h7H,1-6H2,(H,9,10) Key: ZRPLANDPDWYOMZ-UHFFFAOYAK
SMILES O=C(O)CCC1CCCC1
Properties
Chemical formula	C8H14O2
Molar mass	142.198 g·mol^−1
Density	0.996 g/mL^[1]
Melting point	130 to 132 °C (266 to 270 °F; 403 to 405 K) (12 mmHg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The primary use of cypionic acid is in pharmaceutical formulations. Cypionic acid is used to prepare ester prodrugs which have increased half-lives relative to the parent compound. The lipophilicity of the cypionate group allows the prodrug to be sequestered in fat depots after intramuscular injection.^[2] The ester group is slowly hydrolyzed by metabolic enzymes, releasing steady doses of the active ingredient. Examples include testosterone cypionate, estradiol cypionate, hydrocortisone cypionate, oxabolone cipionate, and mesterolone cypionate.

References

1. 3-Cyclopentylpropionic acid at Sigma-Aldrich
2. VJ. Stella, W.N A. Charman and V.H. Naringrekar (1985). "Prodrugs: Do They Have Advantages in Clinical Practice?". Drugs. 29 (5): 455–473. doi:10.2165/00003495-198529050-00002. PMID 3891303.