(3,4-Methylenedioxyphenol)

(3,4-Methylenedioxyphenol) - Names and Identifiers

Name	Sesamol
Synonyms	Sesamol NSC 59256 1,3-Benzodioxol-5-ol 3,4-Methylenedioxyphenol 1,3-Benzodioxol-5-ol, 9CI 3,4-(Methylenedioxy)phenol 3,4-(methylenedioxy)-pheno (3,4-Methylenedioxyphenol) 5-Hydroxy-1,3-benzodioxole 3,4-(Methylenedioxy) phenol 1,2,4-Benzenetriol Methylene ether Methylene ether of oxyhydroquinone 4-Hydroxy-1,2-Methylenedioxybenzene 3,4-METHYLENEDIOXYPHENOL FOR SYNTHESIS 5-Hydroxy-1,3-benzodioxole3,4-Methylenedioxyphenol
CAS	533-31-3
EINECS	208-561-5
InChI	InChI=1/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
InChIKey	LUSZGTFNYDARNI-UHFFFAOYSA-N

(3,4-Methylenedioxyphenol) - Physico-chemical Properties

Molecular Formula	C7H6O3
Molar Mass	138.12
Density	1.2112 (rough estimate)
Melting Point	62-65 °C (lit.)
Boling Point	113-116°C 2mm
Flash Point	113-116°C/2mm
Water Solubility	slightly soluble
Solubility	DMSO : ≥ 100 mg/mL (724.01 mM);Ethanol : ≥ 100 mg/mL (724.01 mM)
Appearance	White to off-white (Solid)
Color	off-white to tan
BRN	127405
pKa	10.08±0.20(Predicted)
Storage Condition	Keep in dark place,Inert atmosphere,Room temperature
Sensitive	Light Sensitive
Refractive Index	1.4850 (estimate)
MDL	MFCD00005827
Physical and Chemical Properties	Gray-brown needle-like crystals, soluble in methanol, ethanol, DMSO and other organic solvents, derived from sesame oil.
Use	Used as antioxidant, pharmaceutical intermediates and cosmetic additives

(3,4-Methylenedioxyphenol) - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	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
TSCA	Yes
HS Code	29329970
Hazard Note	Irritant

(3,4-Methylenedioxyphenol) - Upstream Downstream Industry

Raw Materials

Sulfuric acid

(3,4-Methylenedioxyphenol) - Reference

Reference

1. Wang Nan Nan, Li Xiaodong, Wang Xue de. Enhancement of oxidative stability of cold-pressed sesame oil catalyzed by phospho-tungstic Heteropoly acid and sesamin [J]. China Oils and fats, 2018, v.43;No.327(05):79-83.
2. Chen, Yazhen, et al. "Effect of oncology and in vitro fusion on phenic profiles and antioxant activity of water-soluble extracts from sesame." Food and Chemical Biology 139 (2020): 111239.https://doi.org/10.1016/j.fct.2020.111239
3. [IF = 6.023] Yazhen Chen et al."Effects of thermal preparation and in vitro digestion on lignan profiles and antioxidant activity in defatted-sesame meal."Food Chem Toxicol. 2019 Jun;128:89
4. [IF=6.023] Yazhen Chen et al."Effect of roasting and in vitro digestion on phenolic profiles and antioxidant activity of water-soluble extracts from sesame."Food Chem Toxicol. 2020 May;139:111239
5. [IF=5.396] Yang Yang et al."Sesamol supplementation alleviates nonalcoholic steatohepatitis and atherosclerosis in high-fat, high carbohydrate and high-cholesterol diet-fed rats."Food Funct. 2021 Oct;12(19):9347-9359

(3,4-Methylenedioxyphenol) - Reference Information

NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
sesame oil is an important component	sesame phenol, also known as 3, 4-methylenedioxyphenol, fat-soluble lignans, is an important component of sesame oil and an important quality stabilizer of sesame oil. Sesame phenol exists in sesame seeds, sesame oil and sesame meal, and can be produced by continuous decomposition of sesame linins and the like during thermal processing, up to 64.4 mg/(100g) in sesame oil. sesamol has very strong antioxidant capacity and has been proved to have anti-inflammatory and regulating intestinal function. Antioxidants commonly used in food and medicine. At the same time, it is an important starting material for the synthesis of antihypertensive drugs and cardiovascular drugs. It is also a raw material for the pesticide piperyl butyl ether. Sesamin is very tight in the world, especially in the field of drug synthesis.
application	sesame phenol naturally exists in sesame oil with very little content. This product is an aromatic phenolic compound, which can interact with acids, aldehydes, alcohols (phenols) and other compounds to form esters and ether derivatives. It is widely used in the preparation of a series of fine chemicals such as anti-mold antibacterial agents, anti-cancer, anti-hypertensive drugs, high-grade hair conditioning agents for shampoo, etc. It is an expensive chemical and pharmaceutical intermediate raw material with good development and utilization value and application prospects. It is also an important intermediate for the synthesis of anticancer drugs and pesticide synergists, and also as an intermediate for antihypertensive and cerebrovascular disease drugs.
synthesis method	there are three main synthesis techniques for sesamol: one is extracted from sesame oil, the other is fully synthesized from pepper amine, and the third is a semi-synthetic route from jasmine. The extraction of sesamol from sesame oil has a large solvent consumption and high cost, which is not suitable for industrial production; the total synthesis route starting from piperzine requires diazotization and hydrolysis to obtain a low yield of sesamol. At the same time, due to the diazotization and hydrolysis process, it is inevitable that there will be a coupling side reaction to produce pigment material inclusions. It is difficult to remove in the product, so the color of sesamol is not good, and the application is limited; the semi-synthetic route starting from jasmonal, it is the most industrialized process route, and the product quality and color are very good. Sesame phenol was synthesized from jasmine aldehyde, mainly through two steps of oxidation and hydrolysis. In this project technology, low-cost oxidant and reaction extraction technology are used, so that the generated products quickly leave the reaction zone, greatly reducing the occurrence of side reactions. The yield can reach more than 60%, the product content is 98%, and it is white crystal.
The metabolic pathway of sesamol in the human body	After being ingested, sesamol is absorbed into the body through the gastrointestinal tract. First, part of sesamol is metabolized by two-phase enzymes in the liver. Conjugated products such as sesamol sulfate and sesamol glucuronide, and then the remaining sesamol and its conjugated products are transported to other tissues such as the brain and lungs, it is mainly distributed in the lungs and kidneys and eventually excreted in urine and feces.
Uses	Sesame phenol is an important aroma component of sesame oil and an important quality stabilizer of sesame oil; it is widely used in the preparation of anti-mold and antibacterial agents, anti-cancer, Anti-hypertensive drugs, high-grade hair conditioning agents for shampoo, etc.; it is an expensive chemical and pharmaceutical intermediate raw material with good development and utilization value and application prospects; it is an important intermediate for the synthesis of anticancer drugs and pesticide synergists, and also as an intermediate for antihypertensive and cerebrovascular disease drugs; it is used as food and medicine Sesame phenol naturally exists in sesame oil with very little content. This product is an aromatic phenolic compound, which can interact with acids, aldehydes, alcohols (phenols) and other compounds to form esters and ether derivatives. It is widely used in the preparation of a series of fine chemicals such as anti-mold antibacterial agents, anti-cancer, anti-hypertensive drugs, high-grade hair conditioning agents for shampoo, etc. It is an expensive chemical and pharmaceutical intermediate raw material with good development and utilization value and application prospects. It is also an important intermediate for the synthesis of anticancer drugs and pesticide synergists, and also as an intermediate for antihypertensive and cerebrovascular disease drugs. use as antioxidants, pharmaceutical intermediates and cosmetic additives sealed, cool, dry and dark storage
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)