Sesamol Property

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

pka

10.08±0.20(Predicted)

form 

crystalline

color 

off-white to tan

Water Solubility 

slightly soluble

Sensitive 

Light Sensitive

BRN 

127405

InChIKey

LUSZGTFNYDARNI-UHFFFAOYSA-N

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

SM0890000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29329970

Hazardous Substances Data

533-31-3(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

Sesamol Chemical Properties,Usage,Production

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.

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].