Sesamol

Sesamol powder Base Information

Name	Sesamol powder
Appearence	White powder
Cas	533-31-3
Assay	≥99%
Solubility	nsoluble in water or alcohol, soluble in Acetic acid, ethyl ester.
Molar mass	138.12 g/mol
Melt Point	62 to 65 °C (144 to 149 °F; 335 to 338 K)
Molecular Formula	C7H6O3
Boiling point	21 to 127 °C (250 to 261 °F; 394 to 400 K) at 5
SMILES	mmHgO1c2ccc(O)cc2OC1

 

What’s Sesamol?

Sesamol is a natural phenol compound found in processed sesame oil and roasted sesame seeds. Sesamol (CAS 533-31-3) is considered the major active and potent constituent of sesame oil that play role in its therapeutic effects.

Sesame (Sesamum indicum) is an important oilseed in the family Pedaliaceae. It is regarded as one of the oldest oilseed known and utilized by man for not only its nutritional value but also the medicinal value. The major parts of sesame conferring therapeutic value are leaves and seed oil.

Sesamol 533-31-3 compound is found in trace amounts besides other lignin compounds of sesame oil, sesamin and sesamolin. This water soluble compound is a regarded a strong antioxidant.

 

How does sesamol work?

Sesamol works in different ways to offer its vast therapeutic benefits such as neuroprotection, antioxidant effects, anti-inflammatory, anti-tumor, anti-radiation and radical scavenging effects.

Below are some modes in which sesamol work to achieve the said effects;

 

I. Prevents DNA damage by oxidative stress

Sesamol can inhibit DNA damage by radiation-induced stress. Ionizing radiation causes damage to the cellular DNA by inducing chromosomal aberrations and micronuclei in proliferating cells.

 

II. Stimulates the activity of important antioxidants

Sesamol works by up-regulating the activities of important antioxidant enzymes such as catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GPx), which is accompanied by increased levels of reduced glutathione (GSH). These enzymes play vital roles in preventing cellular damage by radicals.

 

III. Inhibits pro-apoptotic proteins thus enhances cell viability

Pro-apoptotic proteins are proteins that promotes cell death. They include p53, caspase-3, PARP, and Bad enzymes. These enzymes are involved in programmed cell death hence may reduce cell viability.

Sesamol has been demonstrated to promote cell viability by inhibiting the activity of pro-apoptotic enzymes.

 

IV. Inhibition of lipid peroxidation

Lipid peroxidation is a kind of lipid degradation occurring due to oxidation. This results in formation of reactive aldehydes, such as malondialdehyde (MDA) and 4-hydroxynonenal (HNE) that causes cell damage. Sesamol has been shown to prevent lipid peroxidation thus offer protection to cells.

 

V. Inhibits the generation of free radical including hydroxyl radicals

Free radicals are unstable compounds that are associated with diseases and aging. Hydroxyl radicals are the most powerful oxidants that cause illness.

Sesamol decreases the generation of free radicals including hydroxyl, α, α-diphenyl-β-picrylhydrazyl (DPPH), and ABTS(2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) radical.

 

VI. Enhances the radical scavenging activity

In addition to inhibiting the generation of free radicals, sesamol is able to eradicate free radicals such as hydroxyl, lipid peroxyl and tryptophanyl radicals.

 

VII. Suppression of inflammatory cells

Sesamol inhibits the signaling pathways involved in production of reactive species thus minimizes inflammatory response.

 

VIII. Reduces inflammatory cytokines (TNFα, IL-1β, and IL-6)

Nitric oxide, produced by iNOS, leads to lung inflammation by stimulating inflammatory cytokines, such as TNFα, and enhancing the inflammatory response. Sesamol has the ability to inhibit the release of TNFα and IL-1β.

 

IX. Arresting of cell growth at different phases

Sesamol has been shown to induce cell growth arrest at different cell growth phases including the S phase and G0/G1 phase. Sesamol anti cancer properties therefore helps, for instance, reduce cancer cell growth.

 

X. Activation of caspase pathway

The caspases are enzymes involved in programmed cell death. Sesamol has been demonstrated to activate these pathways hence leading to cancerous cell death.

 

XI. Induces apoptosis via intrinsic and extrinsic pathways

Apoptosis is a physiological process in which organized cell death occurs. It is an essential process as it helps the body eliminate dead cells.

Sesamol induces apoptosis in two distinct ways, the intrinsic and extrinsic ways.

 

XII. Hinders mitochondrial autophagy

Mitochondrial autophagy is a particular kind of degradation that helps get rid of defective mitochondria.

When sesamol inhibits this process, then apoptosis is induced.

 

XIII. Reduces nitrite and neutrophil levels

Nitrites and neutrophils play role in inflammatory response. They are involved in the release of nitric oxide which mediates inflammatory response by inducing or otherwise inhibiting inflammation.

Sesamol plays role as anti-inflammatory agent by reducing the levels of nitrites and neutrophils.

 

What’s sesamol used for?

Sesamol is used for various health benefits including;

 

i. High blood pressure.

Sesame oil is used along with a few blood pressure drugs as proven medication to lower blood pressure.

Wide research on sesame oil suggests that sesamol and sesamin (lignans available in sesame oil) play a big role in regulating blood pressure. Taking sesame oil, more so cooking with it, for three weeks lowers the blood pressure for people with hypertension to normal.

During the research, medical practitioners subjected a group of hypertensive patients to medications (Procardia, Nefedica and Adelta) for a period of 21 days. Though there was slight decrease in their blood pressures, it had not normalized. Sesame oil was used as a replacement to the medications, and the patients tested after the same period. The result was that their blood pressure had fallen to normal.

Doctors argued that the resulted were highly contributed by the high amounts of sesamol and sesamin in cooked sesame oil. If was thus found that including sesame oil in diet for people with high blood pressure could be more effective than subjecting them to medication.

These results were reported to American Heart Association during an annual meeting of the Inter-American Society of Hypertension by Professor Devarajan Sankar of Annamalai University, India.

 

ii. Blockage in the bowel.

Research on effects of sesamol on bowel blockage suggests that it could be far much better than aspirin. On a study about ulcerative colitis, an IBD (inflammatory bowel disease), which causes damage to the mucosal tissue through dysregulating the inflammatory system. In a study involving rats, sesamol was found to reduce the activities of inflammation-causing enzymes.

Though aspirin is known to effectively kill inflammation disorders when ingested, it could lead to ulcers development in long-term use. Aspirin causes gastroduedonal injuries by wearing out the cells.

More research indicates that nasogastric intubation of sesamol in patients suffering from minor bowel blockage along with standard care lowers the chances of undergoing a surgery.

 

iii. Heart disease.

Risk factors attributed by cardiovascular diseases have a big portion in world’s mortality and morbidity. They could lead to oxidative stress and if untreated worsen to increment in production pf reactive oxygen species, including distorted antioxidant defense system.

Sesamol uses its anti-oxidative properties to inhibit atherosclectoric cardiovascular diseases risk factors such as hypercholesterolemia, hypertriglyceridemia, high concentration of low-density lipoprotein cholesterol and low high-density lipoprotein.

Further researches have concluded that sesamol has membrane stabilizing and lipid lowering effects. Moreover, it offers protection to myocardium against DOX-induced cardiomyopathy.

 

IV. Child growth.

Sesamol is used in a wide range of child development aspect. In different studies, sesamol used for reducing ADHD in mentally disordered children was termed slightly effective if used in small amounts. The DHA deficiency is very common to children with ADHD.

Over ten researches indicate favorable benefits in ADHA symptoms including in word reading, impulsivity, visual learning, working memory, and hyperactivity.

Infants massaged on sesame oil for four weeks recorded improved growth and physical activeness.

 

v. Diabetes.

Sesamol works effectively as a supplement to diabetes medication to lower the blood sugar levels swiftly. Taking sesamol supplements or rather shifting to sesame oil diet while on diabetes drugs gives a better yield for the work.

In several researches, most involving patients of type 2 diabetes, sesamol have depicted great results. One of the studies involved three groups, each suffering from type 2 diabetes. One group was subjected to sesamol alone, another to daily dose medication of glibenclamide (Glyburide), and the last to both sesamol and Glyburide for a period of about 7 weeks.

Sesamol was reported to have synergetic effect with glyburide, as the combined therapy had lowered both hemoglobin A1c and blood sugar levels significantly, and far of better than either of the single therapies.

Hyperlipidemia. Researchers report that sesamol used for burning cholesterol and other lipids in the blood has given positive results. In a model test, effectiveness of sesamol was tested for on high-fat diet-induced hyperlipidemia, chronic hyperlipidemia, hypercholesterolemia, and acute hyperlipidemia.

Decreased triacylglycerol levels as the end results suggested that sesamol significantly reduces the absorption triacylglycerol. Sesamol is also used to reverse the elevated cholesterol levels.

Studies suggest that sesamol supplement increases cholesterol excretion as well as reducing its absorption.

 

VI. Metabolic syndrome and obesity.

Sesamol is reported to contain various biological capabilities including ability to revert obesity and metabolic disorders. It’s reported to possibly inhibit anti-obesity effects.

Research conducted to test how effective sesamol is on obesity, it was found out that it could regulate hepatic lipid metabolism. This subsequently improved insulin resistance and boosted weight loss. Obesity and its related metabolic disorders are widely related to the lipid accumulation within the body. Reduced accumulation means reversed obesity trend.

Sesamol use increases lipolysis, fatty acid oxidation and reduction rate of hepatic lipogenesis, vital factors in lowering lipid accumulation. These activities (i.e. lipid uptake, synthesis and catabolism) are among many that takes place in the liver.

People using sesamol have reported better hepatic and serum lipids profiles, and also ameliorated insulin sensitivity.

 

vii. Rheumatoid arthritis, Osteoarthritis, and osteoporosis.

Though rheumatoid arthritis, a painful and chronic autoimmune disease, has several chemical therapies, their long-term use is usually hepatotoxic. Sesamol could be a potential natural remedy. Studies investigating the same reported that sesamol has better anti-arthritic and anti-inflammatory effects that effectively ameliorated the effects of rheumatoid arthritis.

Osteoarthritis is a major contributing factor to joint pain, estimated to affect about 15% of global population. Oxidative stress, however, has a great part in skeletal muscle dysfunction. Research on effects of sesamol on osteoarthritis-associated joint pain indicated that taking sesamol supplement for a week could lower the pain. This attributed to the anti-oxidative stress property of sesamol.

Scientists have concluded that a similar process to postmenopausal osteoporosis is under gone to cause ovariectomy, where there’s progressive loss in bone weight and strength. It is therefore found that bone loss is highly attributed by estrogen. Sesamol is reported to bind to estrogen receptors and induce estrogen-responsive genes transcription. The beneficial effects promote bone strength by producing bone matrix proteins.

 

viii. Alzheimer disease, anxiety and stroke.

Alzheimer’s disease is a progressive brain impairment attributing to brain cells degeneration. It commonly eradicates the mental independence of the affected persons. The neuroprotective effects of sesamol have been reported promising. A study was set to elucidate the therapeutic potential of sesamol in epilepsy, a condition widely linked to cognitive impairment and oxidative stress. The research concluded that sesamol exerted ameliorative effects against stroke, cognitive impairment, seizures, and oxidative stress. Sesamol use for antiepileptic medication could be beneficial.

 

Sesamol benefits

[ a ]. Sesamol Anti-oxidant effects

Oxidative stress occurs when there is an imbalance in free radicals’ production and antioxidants in the body. This often leads to cell damage and oxidative stress being regarded as the root cause of many disorders.

Oxidative stress is however a natural physiological process that also leads to aging.

Antioxidants on the other hand are substances that prevent damage of cells due to free radicals. They are often called free radicals scavengers.

Sesamol is the most potent and strong antioxidant component of the sesame oil. It works through different mechanisms to deliver antioxidant effects. These mechanisms of action include up-regulation of important antioxidant activities, DNA protection from radiation damage, scavenging free radicals, inhibiting lipid peroxidation, and protection from ultraviolet radiation.

A study assessing the radioprotective activity of sesamol against gamma irradiation in DNA. DNA damage is induced by introducing single- or double-stranded breaks through the generation of reactive oxygen species.

Sesamol was found to inhibit single-stranded DNA breaks. It also reduced the levels of free radicals specifically the hydroxyl, DPPH, and ABTS radicals, which were all linked to the introduced single- or double-stranded breaks.

 

[ b ]. Sesamol Anti-inflammatory benefits

Inflammation is a natural physiological process that the body employs to fight foreign agents such as bacteria, fungi, or even injury. However, chronic inflammation is harmful to the body as it leads to various disorders.

Anti-inflammatory agents help protect the body from damage by fighting inflammation. Sesamol works through various ways to offer anti-inflammatory effects. These modes of action include inhibiting inflammatory cells, reducing nitrites production as well as suppressing the activity and inflammatory pathways.

In a study of rats with lipopolysaccharide LPS-induced lung injury, sesamol was found to suppress anti-inflammatory cytokines as well as hindered the production of nitric oxide and prostaglandin E2 (PGE2). Sesamol was also found to up-regulate the adenosine monophosphate-activated protein kinase (AMPK) activation. This helps suppress inflammation and also reduce cell damage.

[ c ]. Sesamol anti cancer effects

Sesamol possesses properties that help fight cancerous cells including anti-proliferative activity through various mechanisms such as inhibiting membrane potential, arresting cell growth at different stages as well as inducing apoptosis.

In a study involving DLD-1 human colon cancer cell line, sesamol was used at the dose of 12.5–100 μM. It was found that COX-2 transcriptional activity decreased by 50%.

In another study, sesamol used at a high dosage of 0.5–10 mM was found to induce apoptosis in HCT116 by increasing intracellular reactive oxygen (O2• – ) in a dose-dependent manner. This led to the activation of the JNK signaling pathway that encourages mitochondrial damage. This in turn results in the release of cytochrome c that finally activates caspase thus inducing apoptosis.

 

[ d ]. Seasomol Anti-mutagenic effects

Mutagenicity refers to the ability of an agent (mutagen) to cause mutations. The mutation which is an alteration in genetic material can lead to cell damage and is considered to cause certain illnesses such as cancer.

Sesamol has been shown to possess potent anti-mutagenic properties. Its anti-mutagenic benefits are attributed to the antioxidant activity and more so the ability to scavenge free radicals.

In a study, mutagenicity was induced by the generation of oxygen radicals by tert-butylhydroperoxide (t-BOOH) or hydrogen peroxide (H2O2). Sesamol was found to exert strong anti-mutagenic effects in the Ames tester strains TA100 and TA102. The TA102 strain is known to be highly sensitive to reactive oxygen species. Sesamol was also shown to inhibit the mutagenicity of sodium azide (Na-azide) in the TA100 tester strain.

 

[ e ]. Sesamol Protection from radiation

Radiation refers to the energy that travels in form of waves or particles. Radiation can be occurring abundantly in our environment. However, ionizing radiation can be harmful if left uncontrolled. Short exposure to radiation can lead to acute illnesses such as radiation sickness and sunburn.

Extended exposure to radiation cause more serious disorders including cancer and cardiovascular disease.

In a study of mice with radiation-induced DNA damage, sesamol was evaluated for its protective activity against radiation. Pretreatment of the mice with sesamol resulted in protection against radiation-induced DNA damage.

 

[ f ]. Cardioprotection

Sesamol has been reported to offer protection to the cardiac from injuries.

In a study to evaluate the protective potential of sesamol against myocardial injury, sesamol pretreatment was administered at (50 mg/kg) was done for 7 days before the surgery period.

This study found out that sesamol significantly decreased the infarct size, resorted the cardiac markers, inhibited lipid peroxidation, neutrophil infiltration as well as raised the antioxidants level.it was reported that sesamol powder leads to a decrease in inflammatory genes, Caspase-3 apoptotic proteins, and also enhanced the activity of anti-apoptotic Bcl-2 protein.

 

[ g ]. Sesamol Free radicals scavenging

Free radicals are unstable atoms that easily acquire electrons from other atoms. They are both beneficial and toxic depending on their concentration. At low levels the free radicals play role in the immune response, however, when their concentration is very high they become harmful. Free radicals develop oxidative stress that may damage cells and may cause most chronic and degenerative disorders such as cancer, heart diseases, and arthritis, cataract, and neurodegenerative diseases.

Our bodies counteract the effects of oxidative stress by producing antioxidants however they may not be enough and require supplementation through foods or supplements.

Sesamol possesses’ the ability to inhibit the formation of free radicals as well as scavenge the free radicals.

In a study involving cultured human skin dermal fibroblast adult cells (HDFa) exposed to UVB, sesamol pretreatment was evaluated against cytotoxicity, intracellular reactive oxygen species (ROS) levels, lipid peroxidation, antioxidant status, and oxidative DNA damage. Sesamol was found to significantly reduce lipid peroxidation, cytotoxicity, intracellular ROS, and oxidative DNA damage in the human skin dermal cells. This was attributed to the ability of sesamol supplement to scavenge ROS.

The same study reported increased enzymatic and non-enzymatic activity which contributes to better antioxidant activity.

 

[ h ]. Lowers blood cholesterol

Blood cholesterol is a fat-like, waxy substance in your body. It is needed by the body to build healthy cells but in the right amounts. Cholesterol is transported on two types of lipoproteins, low-density, and high-density. It thus brings about two types of cholesterol, low-density lipoprotein (LDL) cholesterol, and high-density lipoprotein (HDL) cholesterol.

The LDL is often referred to as the bad cholesterol since high levels of LDL increase your risk of coronary artery disorder and other diseases.

Sesamol can decrease the level of cholesterol as well as the level of triacylglycerol in the body.

In a fat tolerance test, sesamol (100 and 200 mg/kg) was found to significantly (P < 0.05) reduce the absorption of triacylglycerol hence lowering the level of triacylglycerol in the body. Triacylglycerol is the main component of fat stored in the adipose tissue.

In a study of Swiss albino mice with induced hyperlipidemia, sesamol supplement at 50 and 100 mg/kg was reported to decrease the levels of both cholesterol and triacylglycerol significantly.

The activity of sesamol reducing the cholesterol and triacylglycerol levels is attributed to its ability to reduce the absorption as well as increase the excretion of cholesterol.

 

[ i ]. Sesamol benefits skin

The human skin is an integral part of the integumentary system whose primary function is to offer protection to the body organs.

Sesamol benefits the skin in various ways due to its potent properties including antioxidant, and anti-inflammatory activity. Sesamol benefits the skin by

 

· Protecting the skin from ultraviolet (UV) rays

Long exposure to sunlight may lead to an elevated abnormal generation of reactive oxygen species (ROS), which may cause skin damage such as collagen degradation in the dermis and hyperplasia of the epidermis.

Sesamol is capable to scavenge the free radicals occurring due to long exposure in sunlight thus protect the skin from radiation DNA damage. It offers a protective coating that helps prevent the skin from being damaged by the UV rays.

Studies report that sesamol can reduce UVB-irradiation-induced cytotoxicity. It is also reported to inhibit melanin biosynthesis by lowering the expression of tyrosinase, MITF, TRP-1, TRP-2, and MC1R in melan-a cells.

Another study found that sesamol may also hinder melanin synthesis by influencing the cAMP/protein kinase A (cAMP/PKA), protein kinase B (AKT)/glycogen synthase kinase 3 beta (GSK3β)/CREB, TRP-1, and MITF in B16F10 cells

 

· Help maintain a glowing skin

Sesamol is known to be a strong antioxidant. It gets deep into the skin thus nourishing the skin. This in turn helps get glowing skin.

 

· Eliminates acne

Acne is a condition in which the skin pores are clogged by oil, dirt, and some harmful microorganisms.

Sesamol possesses antibacterial properties that enable it to get rid of the microorganisms thus you get skin free of acne.

 

· Offers anti-aging effects

Aging is a moderate and continuous process of life. However premature aging could occur due to several factors such as long exposure to UV rays, oxidative stress among others.

Sesamol offers a potent antioxidant activity that prevents the skin and body from cellular oxidation as well as enhances skin rejuvenation.

Sesamol has also been reported to prevent the occurrence of lines, pores, and wrinkles.

 

[ j ]. Sesamol benefits for hair

The topical application of sesame oil nourishes the scalp, hair follicles, and shafts. This promotes healthy hair growth. It also assists in the healing of any damaged scalp by chemicals during hair treatment or dyeing.

Premature greying of hair may occur due to the reduced ability of the body to make enough melanin, as well as other factors such as oxidative stress, genetic modification lifestyle including diet as well as drug use.

Sesamol supplement has proven to be able to maintain the hair color as well as darken the already grey hair.

Besides, sesamol can help eliminate dandruff. Dandruff may occur due to dry skin, allergic reactions to hair products, and the fungus growth on the scalp among other factors. Sesamol helps nourish the skin thus maintain a healthy scalp thus prevents the occurrence of dandruff. The antibacterial activity also ensures the scalp is free of microorganisms that cause dandruff.

 

Three synthetic methods of sesamole

①. Extraction from Sesame oil

Sesamol synthesis from Sesame oil is the easiest of the three methods. However, is quite costly. So this method is not ideal for industrial production, especially due to high production costs.

 

②. Synthetic synthesis originating from piperamine

Although it is fairly economical for large scale Sesamol prodution, the entire route for sesamol synthesis from piperamine applies for small scale production when hydrolysis and hydrolysis process is employed. In such a case, pigment formation as a result coupling and side reaction is unavoidable.

 

③. Semi-synthetic route originating from jasmonaldehyde

Semi-synthetic route originating from jasmonaldehyde is the most widely used sesame phenol synthesis process as far as industrial purposes are concerned. The process involves oxidation and hydrolysis and because of that, the resulting sesame phenol is of high quality and great color.
The process uses cost-efficient oxidant and reactive extraction technology, enabling quick separation of the product from the extraction zone. This minimizes the possibility of side reaction occurrence significantly. No wonder the final product (white-like crystal) is of high quality in terms of colour and sesamol density.

 

Where to buy sesamol

Sesamol powder is available online from different sesamol manufacturers. Most users of sesamol buy from different websites, some for retail or wholesale purposes.

Verify the legitimacy of every sesamol manufacturer using outlined state laws before purchase.

 

References

1. Joo Yeon Kim, Dong Seong Choi and Mun Yhung Jung “Antiphoto-oxidative Activity of Sesamol in Methylene Blue- and Chlorophyll-Sensitized Photo-oxidation of Oil” J. Agric. Food Chem., 51 (11), 3460 -3465, 2003.
2. Kumar, Nitesh & Mudgal, Jayesh & Parihar, Vipan & Nayak, Pawan & Nampurath, Gopalan Kutty & Rao, Chamallamudi. (2013). Sesamol Treatment Reduces Plasma Cholesterol and Triacylglycerol Levels in Mouse Models of Acute and Chronic Hyperlipidemia. Lipids. 48. 633-638. 10.1007/s11745-013-3778-2.
3. Majdalawieh, A. F., & Mansour, Z. R. (2019). Sesamol, a major lignan in sesame seeds (Sesamum indicum): Anti-cancer properties and mechanisms of action. European Journal of Pharmacology, 855, 75–89.DOI: 10.1016/j.ejphar.2019.05.008.
4. Ohsawa, Toshiko. “Sesamol and sesamol as antioxidants.” New Food Industry (1991), 33(6), 1-5.
5. Sesamol Archived 2010-01-14 at the Wayback Machine at Chemicalland21.com
6. Wynn, James P.; Kendrick, Andrew; Ratledge, Colin. “Sesamol as an inhibitor of growth and lipid metabolism in Mucor circinelloides via its action on the malic enzyme.” Lipids (1997), 32(6), 605-610.

 

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