Sesamol Chemical Properties

Melting point:

62-65 °C (lit.)

Boiling point:

113-116°C 2mm

Density 

1.2112 (rough estimate)

refractive index 

1.4850 (estimate)

Flash point:

113-116°C/2mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Methanol

form 

crystalline

pka

10.08±0.20(Predicted)

color 

off-white to tan

Water Solubility 

slightly soluble

Sensitive 

Light Sensitive

BRN 

127405

Cosmetics Ingredients Functions

HAIR DYEING

InChI

1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2

InChIKey

LUSZGTFNYDARNI-UHFFFAOYSA-N

SMILES

Oc1ccc2OCOc2c1

LogP

1.253 (est)

CAS DataBase Reference

533-31-3(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Benzodioxol-5-ol(533-31-3)

EPA Substance Registry System

Sesamol (533-31-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

SM0890000

Hazard Note 

Irritant

TSCA 

TSCA listed

HS Code 

29329970

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

Hazardous Substances Data

533-31-3(Hazardous Substances Data)

MSDS

• Language:English Provider:5-Benzodioxolol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Sesamol Usage And Synthesis

Description

Sesamol is found in sesame seeds and sesame oil. It is a well-known antioxidant. It has antioxidant, chemoprevention, antimutagenic, and antihepatotoxic activities and can induce the apoptosis of cancer and cardiovascular cells. It can be used in the synthesis of paroxetine.

Reference

[1] M. A. Ansari, Z. Fatima, S. Hameed, Sesamol: A Natural Phenolic Compound with Promising Anticandidal Potential, Journal of Pathogens, vol. 2014, Article ID 895193.
[2] T. Geetha, B. Rohit, K. Pal, Sesamol: an efficient antioxidant with potential therapeutic benefits, Medicinal Chemistry, 2009, vol. 5, pp. 367-371.
[3] Amin F. Majdalawieh, Zeenah R. Mansour. “Sesamol, a major lignan in sesame seeds (Sesamum indicum): Anti-cancer properties and mechanisms of action.” European journal of pharmacology 855 (2019): Pages 75-89.
[4] Geetha, T. et al. “Biopharmaceutical profiling of sesamol: physiochemical characterization, gastrointestinal permeability and pharmacokinetic evaluation.” RSC Advances 6 (2014): 4083–4091.

Chemical Properties

off-white to beige crystalline powder

Uses

Sesamol (Paroxetine Anhydrous EP Impurity B) 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.

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 3085, 1978 DOI: 10.1016/S0040-4039(01)94947-0

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 for industrial production. The total synthesis route from piperine requires diazotization and hydrolysis, resulting in a low sesamol yield. Furthermore, the unavoidable coupling side reactions during diazotization and hydrolysis produce pigments that are difficult to remove, leading to poor color and limited applications. The semi-synthetic route from jasmine aldehyde is the most industrially viable, producing a product with excellent quality and color. The synthesis of sesamol from jasmine aldehyde mainly involves two steps: oxidation and hydrolysis. This project utilizes inexpensive oxidants and reaction extraction technology, allowing the product to quickly leave the reaction zone and significantly reducing side reactions. The yield can reach over 60%, with a product purity of 98%, and it is a white crystalline solid.

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].

Sesamol(533-31-3)Related Product Information

• 2-Ethoxyphenol
• p-Anisaldehyde
• Phenol
• (Trifluoromethoxy)benzene
• Phenol Red
• 1,3-Benzodioxole
• 3-Methoxybenzaldehyde
• 3-Aminophenol
• Guaiacol
• Anisole
• p-Anisidine
• 4-Methoxyphenylacetone
• Anemarrhenasaponin-I
• SESAMOLIN
• Sesamin
• XANTHENE-9-CARBOXYLIC ACID
• Sucrose
• Camphor