Description Reference
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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

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Sesamol 533-31-3
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10ton
Release date
2024-05-21
Hebei Longbang Technology Co., Ltd
Product
Sesamol 533-31-3
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20TONS
Release date
2024-04-28
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

533-31-3, SesamolRelated Search:

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

  • 4-Hydroxy-1,2-Methylenedioxybenzene
  • NSC 59256
  • 5-Hydroxy-1,3-benzodioxole 3,4-Methylenedioxyphenol
  • 3,4-METHYLENEDIOXYPHENOL FOR SYNTHESIS
  • 1,2,4-Benzenetriol Methylene ether
  • 1,3-Benzodioxol-5-ol, 9CI
  • 3,4-(methylenedioxy)-pheno
  • Methylene ether of oxyhydroquinone
  • methyleneetherofoxyhydroquinone
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  • 5-Hydroxy-1,2-methylenedioxybenzene
  • Sesamol,3,4-(Methylenedioxy)phenol, 5-Benzodioxolol
  • Paroxetine HCl Anhydrous EP Impurity B
  • S**Sesamol
  • benzo[d][1,3]dioxol-5-ol
  • 4-hydroxy-1,3-benzodioxole
  • Sesamol, 1,3-Benzodioxol-5-ol, 3,4-(Methylenedioxy)phenol
  • SesaMol 98%
  • SesaMe phenol
  • Paroxetine Anhydrous EP Impurity B
  • Sesamol Vetec(TM) reagent grade, 98%
  • SESAMOL
  • 5-HYDROXY-1,3-BENZODIOXOLE
  • 5-BENZODIOXOLOL
  • 3,4-METHYLENDIOXYPHENOL
  • 3,4-METHYLENEDIOXYPHENOL
  • 3,4-(METHYLENEDIOXY)PHENOL, SESAMOL
  • BENZO[1,3]DIOXOL-5-OL
  • 1,3-BENZODIOXOL-5-OL
  • SesaMol, 98% 25GR
  • Paroxetine Impurity 20(Paroxetine HCl Anhydrous EP Impurity B)
  • 1,3-Benzodioxol-5-ol (Sesamol)
  • Sesamol&gt
  • Sesamol (Paroxetine Anhydrous EP Impurity B)
  • Paroxetine EP Impurity B (Sesamol)
  • Sesamolr
  • Paroxetine hydrochloride anhydrous EP Impurity B
  • Sesamol (Paroxetine Impurity)
  • Sesamol (or) 2H-1,3-Benzodioxol-5-ol (or) 1,3-Benzodioxol-5-ol
  • Paroxetine impurities807
  • SesamolQ: What is Sesamol Q: What is the CAS Number of Sesamol Q: What is the storage condition of Sesamol Q: What are the applications of Sesamol
  • Paroxetine Hydrochloride Impurity B
  • 3-4 Metylenedioxy Phenol (Sesamol)
  • Sesamol-RM
  • Sesamol Impurity
  • 533-31-3
  • 33-31-3
  • 1533-31-3
  • Oxygen Compounds
  • Phenols
  • Organic Building Blocks
  • Building Blocks