Dimethylmethoxy chromanol
[CAS# 83923-51-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: Dimethylmethoxy chromanol
• Synonyms: 7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-ol
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• CAS Registry Number: 83923-51-7
• EC Number: 893-588-0
• SMILES: CC1(CCC2=CC(=C(C=C2O1)OC)O)C

Properties

• Solubility: 71.17 mg/L (25 °C water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.528, Calc.^*
• Melting point: 101.71 °C
• Boiling Point: 329.0±42.0 °C (760 mmHg), Calc.^*, 311.52 °C
• Flash Point: 152.8±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS0i9 Warning
• Risk Statements: H411
• Safety Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

Dimethylmethoxychromanol, commonly known as Delta-tocotrienol, is a form of vitamin E. This compound belongs to the tocotrienol family, a class of natural compounds that are structurally similar to tocopherol, another vitamin E. The discovery of Delta-tocotrienol dates back to the 1960s, when researchers began exploring the health benefits of vitamin E. Initially, tocotrienols were considered less important than tocopherols, but studies conducted over the years have revealed the unique properties and benefits of Delta-tocotrienol. Delta-tocotrienol is synthesized by converting geranylgeranyl pyrophosphate, a compound found in certain vegetable oils. It is commonly extracted from palm oil, rice bran oil, and annatto seeds. One of the most notable features of Delta-tocotrienol is its potent antioxidant activity. It exhibits higher antioxidant capacity compared to tocopherol, especially in scavenging lipid peroxide free radicals and protecting cell membranes from oxidative damage. This antioxidant property makes Delta-tocotrienol a promising candidate for protecting cells and tissues from oxidative stress, which is associated with various chronic diseases and the aging process. Research shows that Delta-Tocotrienol has anti-inflammatory, neuroprotective, cardioprotective, and anticancer properties. It has been studied for its ability to reduce inflammation, inhibit tumor growth, lower cholesterol levels, and prevent neurodegenerative diseases such as Alzheimer's and Parkinson's.In addition to its potential health benefits, Delta-Tocotrienol is used in the cosmetics and skincare industries. Due to its antioxidant and anti-aging properties, it is used in various skincare products to fight signs of aging, reduce oxidative damage, and improve skin health.In addition, Delta-Tocotrienol is added to dietary supplements and functional foods to enhance their nutritional value and provide antioxidant support.

References

2020. Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6. Journal of Medicinal Chemistry, 63(15).
DOI: 10.1021/acs.jmedchem.0c00528

2017. Evaluation of the ROS Inhibiting Activity and Mitochondrial Targeting of Phenolic Compounds in Fibroblast Cells Model System and Enhancement of Efficiency by Natural Deep Eutectic Solvent (NADES) Formulation. Pharmaceutical Research, 34(5).
DOI: 10.1007/s11095-017-2124-4

2016. Synthesis and in vitro , ex-vivo and in vivo activity of hybrid compounds linking a potent ROS and RNS scavenger activity with diverse substrates addressed to pass across the blood-brain barrier. European Journal of Medicinal Chemistry, 123.
DOI: 10.1016/j.ejmech.2016.08.007