59-02-9 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 59-02-9 differently. You can refer to the following data:
1. light yellow liquid
2. VITAMIN E is sometimes referred to as the antisterility vitamin, factor X (an earlier designation), chemically vitamin E is alphatocopherol. Active analogues and related compounds include: dl-α-Tocopherol; 1-α-tocopherol; esters (succinate, acetate, phosphate), and β, ζ 1, ζ 2- tocopherols. The principal physiological forms are D-a-tocopherol, tocopheronolactone, and their phosphate esters.
Originator
Doppelherz,Queisser Pharma,Germany
Uses
Different sources of media describe the Uses of 59-02-9 differently. You can refer to the following data:
1. vitamin E, antioxidant
2. α-Tocopherol is the most bioactive of the naturally occurring forms of Vitamin E. Richest sources are green vegetables, grains, and oils, particularly palm, safflower and sunflower oils.
3. Use in insect cell culture applications as an antioxidant.
Definition
ChEBI: An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.
Manufacturing Process
Manufacturing process for Vitamin E, that is, α-tocopherol (5,7,8-trimethyltocol) in the
past has been accomplished primarily by reacting trimethylhydroquinone
(TMHQ) with isophytol (3,7,11,15-tetramethylhexadec-1-en-3-ol) or phytol
(3,7,11,15-tetramethylhexadec-2-en-1-ol) in a condensation reaction. The
reaction is well known and has been practiced for many years (StallaBourdillon, Ind. Chim. Belg., 35, 13 (1970); "The Vitamins" Vol. 5, pages 168-
223, Academic Press, New York, 1967).
The Synthesis of Vitamin E includes these steps as follows: Rearrangement to C15 Acetylene; Saponification of the C20 Dienol Acetate to Dehydrophytol;Condensation of Dehydrophytol with TMHQ to yield Dehydro-Vitamin E.
Therapeutic Function
Antioxidant
General Description
α-Tocopherol is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase. It is the major form of Vitamin E in human plasma. It is present in sunflower seed oil.
Health Hazard
The physiological functions of vitamin E substances include: (1) bio logical antioxidant; (2) normal growth maintenance; (3) protects unsaturated fatty acids and membrane structures; (4) aids intestinal absorption of unsaturated fatty acids; (5) maintains normal muscle metabolism; (6) maintains integrity of vascular system and central nervous system; (7) detoxifying agent; and (8) maintains kidney tubules, lungs, genital structures, liver, and red blood cell membranes.In livestock and laboratory animals, a deficiency of vitamin E substances may cause degeneration of reproductive tissues, muscular dystrophy, encephalomalacia, and liver necrosis. Considerable research is required to fully determine supplementation of livestock diets unless typical symptoms of a deficiency appear. Symptoms have appeared where there are selenium deficiencies in the soil and where there are excessive levels of nitrates in the soil. “White muscle” is the term used to describe a condition of muscular dystrophy in cattle.
Biochem/physiol Actions
α-Tocopherol is essential for the photosynthesis in Synechocystis sp. strain PCC 6803. Supplementation with α-Tocopherol decreases lipid peroxidation and platelet aggregation. It inhibits protein kinase C and may play key role in gene regulation.
Safety Profile
Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits acrid smoke and irritating fumes.
Purification Methods
Vitamin E is a viscous yellow oil which is distilled at high vacuum. It has max at 294nm (E1cm 1% 71). It is oxygen and light sensitive and is best stored as its stable D--acetate [58-95-7] which is purified by evaporative distillation at b 180-200o(bath temperature)/0.7mm, and has [] D 25 +3.3o (c 5.1, EtOH). It forms needles at -30o and has m 26.5-27.5o, [] D 25 +0.25o (c 10, CHCl3). [NMR: Cohen et al. Helv Chim Acta 6 4 1158 1981, Burton & Ingold Acc Chem Res 1 9 194 1986, Karrer et al. Helv Chim Acta 2 1 520 1938, Robeson J Am Chem Soc, 64 1487 1942, 65 1660 1943.] Of the eight isomers the D--isomer is the most active. [See W. Friedrich “Vitamins” Walter de Guyter Publ, Berlin 1988.] [Beilstein 17/4 V 168.]
Check Digit Verification of cas no
The CAS Registry Mumber 59-02-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 59-02:
(4*5)+(3*9)+(2*0)+(1*2)=49
49 % 10 = 9
So 59-02-9 is a valid CAS Registry Number.
59-02-9Relevant articles and documents
Novel PEGylated derivatives of α-tocopherol for nanocarrier formulations; synthesis, characterization and in vitro cytotoxicity against MCF-7 breast cancer cells
Esmaeelzadeh, Maryam,Mazarei, Zeinab,Rafati, Hasan,Salehi, Peyman,Savadkouhi, Niloofar
supporting information, (2021/03/17)
Despite numerous beneficial therapeutic effects namely antioxidant and anti-inflammatory activity, Vitamin E has limited clinical applications due to its low water solubility. Throughout the present work, α-tocopherol's new PEGylated derivatives alongside with polyethylene glycol 300 (α-TPGT300), 400 (α-TPGT400), and 1000 (α-TPGT1000) were synthesized. A 1,2,3-triazole ring was utilized as a linker for the attachment of alpha tocopherol to the PEGs through a click reaction. The purified derivatives were characterized by the means of 1H NMR, 13C NMR, mass spectroscopy, UV–vis and FT-IR methods. Synthesized derivatives’ capacity to produce self-assembly nanoparticles was evaluated employing the critical micelle concentration (CMC) values. The stability of the micelles was studied by size analysis. In vitro cytotoxicity of the products was investigated using MTT assay against MCF-7 breast cancer cells. The IC50 value for TPGT1000 after 24 h treatment was 15.0 ± 1.8 μM, whereas no significant cytotoxicity effect was observed following the treatment of MCF-7 cells by TPGT300, 400. The present study showed that polymeric micelle TPGT1000 possessed better physicochemical and biological properties including relatively lower CMC value, higher stability in FBS environment in addition to higher cytotoxicity against MCF-7 breast cancer cells compared to the lower molecular weight PEGylated derivatives. These results confirmed that increasing PEG chain length left a positive effect on the polymeric micelle properties and also improved the cytotoxicity effect of new PEGylated vitamin E derivatives.
A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK
Pan, Wenjing,Li, Chenchen,Zhu, Haoyin,Li, Fangfang,Li, Tao,Zhao, Wanxiang
, p. 7633 - 7640 (2021/09/22)
A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.
Imidazole ionic liquid, preparation method thereof, and application thereof in synthesis of vitamin E acetate
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Paragraph 0032-0051, (2019/05/02)
The invention discloses an imidazole ionic liquid, a preparation method thereof, and an application thereof in the synthesis of vitamin E acetate. The structure of the imidazole ionic liquid is represented by formula (I) shown in the description, and Y in the formula (I) is ZnCl2Br or ZnBr. The catalyst has the advantages of cheapness, easiness in obtaining, and stable performances, and has the advantages of good catalytic activity, simple reaction process, mild reaction conditions, high conversion rate and selectivity and no pollution when used in catalytically synthesizing the reaction of vitamin E.
