INTRODUCTION
Teprenone (Geranylgeranylacetone, GGA) is a mixture of the all-trans and mono-cis isomers of 6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraen-2-one (in a weight ratio of 3:2). It is an acyclic isoprenoid compound with a structure like retinoids and is widely used for the treatment of gastrointestinal ulcers.
MANUFACTURE
Geraniol is first transformed into geranyl acetone through a two-step process involving in-situ bromination and substitution followed by decarboxylation. The resulting geranyl acetone is then converted to trans-farnesol via a Wittig reaction, followed by reduction of the corresponding ester. Subsequently, trans-farnesol undergoes a series of controlled reactions, including tosylation, substitution, decarboxylation, Grignard reaction, and oxidation, ultimately yielding teprenone.
| Synonyms | 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one; Selbex |
| CAS no. | 6809-52-5 |
| EC no. | 614-276-0 |
| Molecular formula | C23H38O |
| Molecular weight | 330.55 |
| Structure |  |
APPLICATIONS
Geranylgeranylacetone has several industrial and pharmaceutical applications due to its low toxicity and strong cytoprotective effects
| Pharmaceuticals |
| Marketed as Teprenone serves as an important isoprenoid intermediate in pharmaceutical synthesis. |
| • Used for treatment of gastric ulcers and protection of gastric mucosa. |
| • Prevention and treatment of viral hepatitis, particularly in the prevention and treatment of hepatitis B and hepatitis C. |
| Skin Protection, Cytoprotective & Anti-Aging applications |
| • It is known to induce heat shock proteins (HSP70) and enhances cellular protection against stress. |
| • Teprenone can protect cells in various organs, such as the eye, brain, and heart. |
| • Protection against oxidative stress. |
| Potential Therapeutic Areas (Research Stage) |
| Used for: |
| • Treatment of neurodegenerative diseases (e.g., Alzheimer’s, Parkinson’s) |
| • Cardiovascular protection |
| • Liver protection. |
| Industrial / Chemical Use |
| • Intermediate in terpenoid chemistry research |
| • Used in biochemical studies involving isoprenoid pathways. |
SPECIFICATIONS
| Test | Unit | Specification |
|---|---|---|
| Appearance | – | Colorless to light yellow or orange oily liquid |
| Purity (GC) (Two isomers) | % area | Not less than 99.0 |
| Identification by IR | – | Should Conform to structure of the molecule |
| Water content (KF) | % w/w | Not more than 0.50 |
| n-Heptane (GC-RS) | ppm | Not more than 5000 |
STORAGE & PRECAUTION
Store at 2-8 °C in a well closed container.
PACKING
Globally compliant packaging
REACH Status
Not registered
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