Chemical Properties
off-white to beige crystalline powder
Uses
Sesamol is a natural component of sesame oil with antioxidant activity. Sesamol has potential protective effects against free radicals as well as some antifungal activity. Sesamol can also be used as
an intermediate in the preparation of antidepressants such as Paroxetine (P205750).
Definition
ChEBI: Sesamol is a member of benzodioxoles.
benefits
Sesamol, 5-hydroxy-1,3-benzodioxole or 3,4-methylene-dioxyphenol, is a water-soluble phenolic lignan isolated from roasted sesame seeds and processed sesame oil. Various studies investigated the anti-cancer therapeutic potential of sesamol, and the literature provided reveals compelling evidence that sesamol acts as a metabolic regulator and possesses antioxidant, anti-mutagenic, anti-hepatotoxic, anti-inflammatory, anti-aging, and chemopreventive properties.
General Description
Sesamol, a principal phytophenol of sesame oil lignans, is typically used as a dietary compound.(10)
Biological Activity
Sesamol has a wide range of biological actions including inhibition of lipid peroxidation and enhancement of radical scavenging, upregulation of antioxidant enzymes, suppression of TNFα 80 and IL-1β expression, inhibition of NF-κB 81 signaling, suppression of LOX-1 82 and 5-LOX activity, induction of 83 apoptosis, arresting cell growth at different phases of the cell cycle; and modulation of caspase-3, p53, Bax, and Bcl2 expression[3].
Pharmacokinetics
Sesamol (100 mg/kg body weight in rats) is reportedly eliminated from the body within 0-4 hours of oral administration as conjugates. The maximum plasma concentration (Cmax), half-life (t1/2), and area under the curve (AUC) of sesamol were found to be 1.4±0.7 μg/mL, 563.7±36.9 min, and 501.3±200.8 min μg/mL, respectively, following oral administration of 50 mg/kg body weight dose of sesamol to rats. A rapid decline in plasma concentrations and an oral bioavailability (BA) of 35.5 ± 8.5% has been reported for sesamol in Sprague Dawley rats. Sesamol is reported to undergo reductive cleavage to 2-methoxybenzene-1,4-diol and benzene-1,2,4-triol. Small quantities of these metabolites are observed in the urine of rats fed with sesamol. Moreover, sesamol or its metabolite was not detected when sesamol was incubated in vitro with rat faecal microbiota. Sesamol is excreted unchanged in the excreta, while it is a glucuronide in the urine. It is indicated that sesamol and its conjugated metabolites are rapidly eliminated from urine and feces in 0–4 h[4].
Synthesis
There are three main synthetic techniques for sesamol: extraction from sesame oil, total synthesis from piperine, and semi-synthetic route from jasmine aldehyde. Extraction from sesame oil involves high solvent consumption and cost, making it unsuitable f
Solubility in water
Sesamol shows solubility of ~10 mg/mL (9.50-11.08 mg/ml) at all the pH<9. Further, there is a sharp increase in solubility at more alkaline pH>10, with the value being 41.83 mg/mL at pH 13[4].
