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
Appearance	Liquid
Density	0.996 g/mL[1]
Melting point	12 °C (54 °F; 285 K)
Boiling point	130 to 133 @12mmHg
Hazards
Flash point	122 ± 9.8 °C
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.