| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H26O3 |
| Molecular Weight | 278.3865 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC(=O)CCC1=CC(OC)=C(O)C=C1
InChI
InChIKey=CZNLTCTYLMYLHL-UHFFFAOYSA-N
InChI=1S/C17H26O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h10,12-13,19H,3-9,11H2,1-2H3
| Molecular Formula | C17H26O3 |
| Molecular Weight | 278.3865 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
1-(4-hydroxy-3-methoxyphenyl)decan-3-one (Paradol, 6-paradol ), a major constituent of A. melegueta seeds, exhibited potent proliferative and ossification characteristics in bone cells. It enhanced alkaline phosphatase activity and vitamin D content and decreased the osteoporotic marker acid phosphatase. Paradol enhanced the expression of osteocyte and osteoblast-related genes and inhibited osteoclast and RUNX suppressor genes. Paradols are unsaturated ketones produced by biotransformation of shogaols in gingers. Among them, 6-paradol has been investigated as a new drug candidate due to its anti-inflammatory, apoptotic, and neuroprotective activities. 6-paradol exhibited a significant
glucose-lowering effect and decreased body weight. 6-paradol possesses good anti-hyperglycemic activity, therefore it may serve as a novel
target for the development of anti-obesity and anti-hyperglycemic functional food. 6-paradol effectively protects brain after cerebral ischemia, likely by attenuating neuroinflammation in microglia, suggesting it as a potential therapeutic agent to treat cerebral ischemia.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Mice: Compared with the HFD group, the treatment with 1-(4-hydroxy-3-methoxyphenyl)decan-3-one (6-paradol) low dose (6.75 mg/kg/day) or high dose (33.75 mg/kg/day), as well as with pioglitazone
(6.75 mg/kg/day) significantly lowered the blood glucose at the 30-, 60- and 120-min time points.
Route of Administration:
Oral
In 3T3-L1 adipocytes, 6-paradol increased glucose utilization by the cells in a concentration-dependent manner, with insulin EC50 53.2 ± 5.5 uM and without insulin EC50 65.4 ± 5.3 uM. The similar effect was also observed in C2C12 myotubes, with insulin EC50 54.2 ± 4.7 uM and without insulin EC50
54.9 ± 3.3 uM. Moreover, our results revealed that 6-paradol inhibited lipid synthesis in 3T3-L1 cells, reducing the cellular lipid accumulation in a concentration-dependent manner, with
insulin EC50 13.3 ± 3.3 uM and without insulin EC50 29.8 ± 1.4 uM.