119-98-2

Basic information

• Product Name: RAC-TOCOL
• Synonyms: RAC-TOCOL;TOCOL;(2R)-3,4-Dihydro-2-methyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol;Vitamin E Related Compound (2-Methyl-2-(4,8,12-Trimethyltridecyl)-6-Chromanol)
• CAS NO: 119-98-2
• Molecular Formula: C₂₆H₄₄O₂
• Molecular Weight: 388.62636
• Mol File: 119-98-2.mol

Chemical Properties

• Boiling Point: bp0.001 165-175°
• Flash Point: 196.7°C
• Appearance: /
• Density: 0.938g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: RAC-TOCOL(CAS DataBase Reference)
• NIST Chemistry Reference: RAC-TOCOL(119-98-2)
• EPA Substance Registry System: RAC-TOCOL(119-98-2)

Safety Data

• Hazardous Substances Data: 119-98-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
RAC-TOCOL is used as a pharmaceutical agent for its unique properties that do not suppress retinol-induced erythrocyte hemolysis or increase microviscosity of rat liver phosphatidylcholine (PC) liposomes. This characteristic can be beneficial in the development of new drugs or therapies that require a vitamin E derivative with these specific properties.
Used in Cosmetic Industry:
RAC-TOCOL can be used as an ingredient in the cosmetic industry, where its unique properties may provide benefits in the development of skincare products, such as creams, lotions, or serums. The absence of certain effects observed in (±)-α-tocopherol could make RAC-TOCOL a preferred choice for formulations that require specific characteristics.
Used in Research and Development:
RAC-TOCOL's distinct properties make it an interesting compound for research and development in various fields, including pharmacology, biochemistry, and materials science. Its unique behavior in comparison to (±)-α-tocopherol can lead to new discoveries and innovations in these areas.

InChI:InChI=1/C26H44O2/c1-20(2)9-6-10-21(3)11-7-12-22(4)13-8-17-26(5)18-16-23-19-24(27)14-15-25(23)28-26/h14-15,19-22,27H,6-13,16-18H2,1-5H3

Upstream product

• 103-16-2 4-Benzyloxyphenol 
• 150-86-7 phytol 
• 150-76-5 4-methoxy-phenol 
• 123-31-9 hydroquinone 
• 395645-30-4 (3RS,7R,11R)-3,7,11,15-tetramethylhexadec-1-en-3-ol 
• 65592-98-5 1-chloro-3,7,11,15-tetramethylhexadec-2-ene 
• 253686-88-3 (E)-3,7,11,15-tetramethylhexadec-2-en-1-ol 
• 505-32-8 isophytol 
• 16825-16-4 (6R,10R)-6,10,14-trimethylpentadecan-2-one 

Downstream Products

• 2668-47-5 2,6-di(t-butyl)-4-phenylphenol 
• 34004-57-4 tocol radical 

Relevant articles and documents

A New Catalytic System for the Preparation of Chromanols

In the presence of the cation exchange resin complexes of metal ions, hydroquinone, resorcinol, and catechol reacted with phytyl chloride to give chromanols in good yields.The enhanced activity of the catalysts compared with the corresponding metal halides has been ascribed to the participation of the sulfonyl group in the abstraction of the proton on the benzene ring or the hydroxyl group.The catalysts were recycled several times with little loss of activity.

NOVEL USE OF SUBSTITUTED CHROMAN-6-OLS WITH EXTENDED LIPOPHILIC SIDE CHAINS

The present invention is directed towards the use of substituted chroman-6-ols with extended lipophilic side chains of formula (I) wherein one of the two substituents R1 and R2 is C12-21-alkyl and the other of the two substituents R1 and R2 is either hydrogen or C1-5-alkyl or (CH2)n-OH with n being an integer from 1 to 5, and wherein A is CH(R3), and wherein R3, R4 and R6 are independently from each other H or C1-4-alkyl, and wherein R5 is H or OH or C1-4-alkyl or C1-4-alkoxy; with the proviso that at least two of R4, R5 and R6 are not methyl, when R3 is H, and one of the substituents R1 and R2 is methyl and the other of the two substituents R1 and R2 is C12-21-alkyl, as antioxidants in PUFA-containing edible oils such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil for human consumption. The present invention is further directed towards these PUFA containing edible oils comprising such substituted chroman-6-ols with extended lipophilic side chains of formula (I). The present invention is further directed to a method of preserving the shelf life of PUFAs and/or their esters in an edible oil comprising the step of adding at least one compound of formula (I) to said edible oil, as well as to a method of limiting the amount of oxidation of PUFAs and/or their esters in an edible oil which is exposed to air, comprising adding at least one compound of formula (I) to said edible oil, preferably in an amount of said compound of formula (I) ranging from 10 to 500 ppm, preferably ranging from 30 to 300 ppm, more preferably ranging from 100 to 250 ppm, based on the total amount of the edible oil.

NOVEL USE OF SUBSTITUTED CHROMAN-6-OLS WITH EXTENDED LIPOPHILIC SIDE CHAINS

The present invention is directed towards the use of substituted chroman-6- ols with extended lipophilic side chains of formula (I) wherein one of the two substituents R1 and R2 is C12-21-alkyl and the other of the two substituents R1 and R2 is either hydrogen or C1-5-alkyl or (CH2)n-OH with n being an integer from 1 to 5, and wherein A is CH(R3), and wherein R3, R4 and R6 are independently from each other H or C1-4-alkyl, and wherein R5 is H or OH or C1-4-alkyl or C1-4-alkoxy; with the proviso that at least two of R4, R5 and R6 are not methyl, when R3 is H and one of the substituents R1 and R2 is methyl and the other of the two substituents R1 and R2 is C12-21-alkyl, as antioxidants, especially in feed such as pet food and feed ingredients such as fish meal, insect meal and poultry meal, as well as PUFA-containing oil such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil. The present invention is further directed towards feed ingredients and feed for insects, aquatic and terrestrial animals comprising such substituted chroman-6-ols with extended lipophilic side chains of formula (I).

An Enzyme-catalyzed Synthesis of Natural α-Tocopherol

The natural α-tocopherol was synthesized by enzyme-catalyzed enantioselective hydrolysis.The unnatural enantiomer as a by-product was also converted to natural α-tocopherol by racemization and repeated enzyme-catalyzed hydrolysis.

Isoprenoid derivatives and anti-ulcer agents containing the same

Anti-ulcer agents containing isoprenoid derivatives are provided. The isoprenoid derivatives are represented by the formula: STR1 wherein: R represents a group of formula STR2 In the above formula, R1, R2 and R3 may be the