| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H16O |
| Molecular Weight | 152.2334 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)[C@@H]2CC[C@@](C)(C2)C1=O
InChI
InChIKey=LHXDLQBQYFFVNW-XCBNKYQSSA-N
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m1/s1
| Molecular Formula | C10H16O |
| Molecular Weight | 152.2334 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
(+)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. This component has camphoraceous fragrance. (+)-Fenchone is used as a food flavour and in perfumes. Although, there are report that (+)-fenchone has toxic. P450 enzymes are shown to detoxify and/or toxify these compounds to metabolites more polar and sometimes more reactive metabolites. (+)-fenchone are oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives in human liver microsomes. CYP2A6 is suggested to be a principal enzyme in catalyzing (+)-fenchone 6-exo and 6-endo hydroxylation by human liver microsomes. 10-Hydroxylation of (+)-fenchone is also metabolized by CYP2B6.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
Patents
Sample Use Guides
(+)-Fenchone hydroxylation activities by P450 enzymes were determined as follows. Standard reaction mixture contained human liver microsomes (0.1 mg/ml) or recombinant P450 (10 pmol/ml) with 100 uM concentration of (+)-fenchone in a final volume of 0.5 ml of 100 mM potassium phosphate buffer (pH 7.4) containing an NADPH-generating system consisting of 0,5 mM NADP+, 5 mM glucose 6-phosphate, and 0.5 unit of glucose 6-phosphate dehydrogenase/ml. The organic phase was transferred to an insert for analysis by gas chromatography-mass spectrometry. CYP2A6 and CYP2B6 in human liver microsomes were major enzymes involved in the hydroxylation of (+)-fenchone.