Sesamol

Description Reference

Product Name: Sesamol
CAS No.: 533-31-3
Chemical Name: Sesamol
Synonyms: benzo[d][1,3]dioxol-5-ol;SesaMe phenol;1,3-BENZODIOXOL-5-OL;5-BENZODIOXOLOL;3,4-METHYLENEDIOXYPHENOL;SESAMOL;Sesamolr;NSC 59256;S**Sesamol;Sesamol>
CBNumber: CB2413594
Molecular Formula: C7H6O3
Formula Weight: 138.12
MOL File: 533-31-3.mol

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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)

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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)

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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..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: S3003
Product name: Sesamol
Purity: 98%
Packaging: 5G
Price: $38.5
Updated: 2024/03/01

Sigma-Aldrich

Product number: S3003
Product name: Sesamol
Purity: 98%
Packaging: 25g
Price: $88.4
Updated: 2024/03/01

Sigma-Aldrich

Product number: PHL80111
Product name: Sesamol
Purity: phyproof? Reference Substance
Packaging: 50MG
Price: $262
Updated: 2024/03/01

Sigma-Aldrich

Product number: 41557
Product name: Sesamol
Purity: analytical standard
Packaging: 100mg
Price: $74.7
Updated: 2022/05/15

TCI Chemical

Product number: S0418
Product name: Sesamol
Purity: >98.0%(GC)
Packaging: 25g
Price: $66
Updated: 2024/03/01

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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.
[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].

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 Preparation Products And Raw materials

Raw materials

Sulfuric acid

Preparation Products

Pentoxyverine

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Sesamol Suppliers

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View Lastest Price from Sesamol manufacturers

HebeiShuoshengImportandExportco.,Ltd

Product: Sesamol 533-31-3
Price: US $6.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 2000KG/Month
Release date: 2024-08-09

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD

Product: Sesamol 533-31-3
Price: US $999.00-666.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 5000
Release date: 2024-08-09

Hebei Chuanghai Biotechnology Co,.LTD

Product: Sesamol 533-31-3
Price: US $5.00-2.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10000kg
Release date: 2024-08-20

533-31-3, SesamolRelated Search:

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