| Identification | More | [Name]
Sesamol | [CAS]
533-31-3 | [Synonyms]
1,3-BENZODIOXOL-5-OL
3,4-METHYLENDIOXYPHENOL
3,4-METHYLENEDIOXYPHENOL
3,4-(METHYLENEDIOXY)PHENOL, SESAMOL
5-BENZODIOXOLOL
5-HYDROXY-1,3-BENZODIOXOLE
BENZO[1,3]DIOXOL-5-OL
SESAMOL
3,4-(methylenedioxy)-pheno
Methylene ether of oxyhydroquinone
methyleneetherofoxyhydroquinone
Phenol, 3,4-(methylenedioxy)-
SESAMOL 99+%
Sesamol (Paroxetine intermediate)
Sesamol,98%
SESAMOL(RG)
3,4-(Methylenedioxy)phenol, 5-Benzodioxolol
3,4-(Methylenebisoxy)phenol
5-Hydroxy-1,2-methylenedioxybenzene | [EINECS(EC#)]
208-561-5 | [Molecular Formula]
C7H6O3 | [MDL Number]
MFCD00005827 | [Molecular Weight]
138.12 | [MOL File]
533-31-3.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to beige crystalline powder | [Melting point ]
62-65 °C (lit.) | [Boiling point ]
113-116°C 2mm | [density ]
1.2112 (rough estimate) | [refractive index ]
1.4850 (estimate) | [Fp ]
113-116°C/2mm | [storage temp. ]
−20°C
| [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 | [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]
533-31-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
SM0890000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29329970 | [Hazardous Substances Data]
533-31-3(Hazardous Substances Data) |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [Chemical Properties]
off-white to beige crystalline powder | [Uses]
Sesamol 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]. | [storage]
Store at -20°C |
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