59-02-9

Basic information

• Product Name: D-alpha-Tocopherol
• Synonyms: (2r-(2r*(4r*,8r*)))-yl);(2r,4’r,8’r)-alpha-tocopherol;(all-r)-alpha-tocopherol;[2theta-[2theta(4theta,8theta)]]-yl);2H-1-Benzopyran-6-ol,3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-,[2R-[2R*(4R*,8R*)]]-;2r,4’r,8’r)-alpha-tocopherol;3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-1-benzopyran-6;almefrol
• CAS NO: 59-02-9
• Molecular Formula: C₂₉H₅₀O₂
• Molecular Weight: 430.71
• EINECS: 200-412-2
• Product Categories: PHARMACEUTICALS;Organics;Antioxidant;Biochemistry;Vitamins;Vitamins and derivatives;Miscellaneous Compounds;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Used to vitamin E deficiency caused by abortion, habitual abortion and premonitory abortion prevention, also used in sterility;Inhibitors
• Mol File: 59-02-9.mol

Chemical Properties

• Melting Point: 2.5-3.5 °C
• Boiling Point: 200-220 °C0.1 mm Hg(lit.)
• Flash Point: 253 °C
• Appearance: clear yellow/oil
• Density: 0.95 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.505(lit.)
• Storage Temp.: 2-8°C
• Solubility: Practically insoluble in water, freely soluble in acetone, in anhydrous ethanol, in methylene chloride and in fatty oils.
• PKA: 11.40±0.40(Predicted)
• Water Solubility: INSOLUBLE
• Stability: Stable. Combustible. May be sensitive to light and air. Incompatible with strong oxidizing agents.
• Merck: 14,9495
• BRN: 4712525
• CAS DataBase Reference: D-alpha-Tocopherol(CAS DataBase Reference)
• NIST Chemistry Reference: D-alpha-Tocopherol(59-02-9)
• EPA Substance Registry System: D-alpha-Tocopherol(59-02-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26
• WGK Germany: 1
• RTECS: DJ2900000
• F: 8-10-23
• Hazardous Substances Data: 59-02-9(Hazardous Substances Data)

Usage

Uses

Used in Antioxidant Applications:
Vitamin E is used as an antioxidant to protect cells from oxidative damage caused by free radicals. It helps to maintain the integrity of cell membranes and supports overall health and well-being.
Used in Food Industry:
Vitamin E is used as a preservative and antioxidant in the food industry to extend the shelf life of products and maintain their quality.
Used in Cosmetics and Skincare Industry:
Vitamin E is used in cosmetics and skincare products for its antioxidant and moisturizing properties, helping to protect the skin from environmental damage and promote a healthy complexion.
Used in Insect Cell Culture Applications:
Vitamin E, specifically α-tocopherol, is used as an antioxidant in insect cell culture applications to maintain the health and viability of the cells during the culture process.

Originator

Doppelherz,Queisser Pharma,Germany

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

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.]

Synthetic route

titanium montmorillonite + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
In octane	100%

(2R,4'R,8'R)-α-tocopheryl methyl ether (32466-45-8) → Tocopherol (59-02-9)

Conditions	Yield
Stage #1: (2R,4'R,8'R)-α-tocopheryl methyl ether With triethylsilane; tris(pentafluorophenyl)borate at 20℃; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃;	100%
With aluminum (III) chloride; boron dimethyl-trifluoro sulphide In dichloromethane; acetonitrile at 20℃;	84%
With aluminum (III) chloride; boron trifluoride dimethyl sulfide In dichloromethane; acetonitrile at 0 - 20℃; for 6h;	78%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; Zinc chloride In tetrachloromethane	99.1%
With hydrogenchloride; sodium dithionite; Zinc chloride In toluene	99.8%
With hydrogenchloride; zinc dibromide; zinc	98.6%

2-methylpropyl acetate (110-19-0) + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; Zinc chloride In water; toluene	99.6%
With hydrogenchloride; Zinc chloride In water; toluene	98.6%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + Diethyl carbonate (105-58-8) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; sodium chloride; Zinc chloride In water; toluene	99.2%
With hydrogen bromide; zinc dibromide In water	99.1%
With hydrogenchloride; Zinc chloride In water; toluene	98.9%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + butanone (78-93-3) → Tocopherol (59-02-9)

Conditions	Yield
With sodium hydroxide; sodium chloride; scandium tris(trifluoromethanesulfonate) In ethyl acetate; toluene	99%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + butan-1-ol (71-36-3) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; Zinc chloride In hexane; water; toluene	98.1%
With hydrogenchloride; Zinc chloride In hexane; water; toluene	98.1%
With hydrogenchloride; Zinc chloride In hexane; water; toluene	95.9%
With hydrogenchloride; Zinc chloride In hexane; water; toluene	95.9%

Trimethylhydroquinone (700-13-0) + isophytol → Tocopherol (59-02-9)

Conditions	Yield
aluminum ion-exchanged montmorilonites In octane for 3h; Product distribution; Heating; var. metal ion-exchanged montmorilonites, var. solvents, var. reaction time;	98%

scandium fluorosulfonate + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With sodium chloride In ethyl acetate; toluene	98%

2-((7R,11R)-3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylbenzene-1,4-diol (14745-36-9) → Tocopherol (59-02-9)

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 80℃; for 1.25h;	95%
With toluene-4-sulfonic acid In benzene Heating;
With toluene-4-sulfonic acid In toluene at 45℃;

(2R,4'R,8'R)-5-(morpholinomethyl)-γ-tocopherol (6991-51-1) → Tocopherol (59-02-9)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In 2-methyl-propan-1-ol for 9h; Heating;	95%

scandium bentonite + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
In hexane; toluene	93%

4-methoxybenzyl (R,R,R)-α-tocopheryl ether (1402580-98-6) → Tocopherol (59-02-9)

Conditions	Yield
With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 6h;	93%

isophytol (505-32-8) → Tocopherol (59-02-9)

Conditions	Yield
In toluene	91%
	88.7%

camphor-10-sulfonic acid (76-26-6, 3144-16-9, 5872-08-2, 35963-20-3) + 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione (7559-04-8) → Tocopherol (59-02-9)

Conditions	Yield
	90.3%

(2R,4'R,8'R)-1',2'-dehydro-α-tocopheryl benzyl ether → Tocopherol (59-02-9)

Conditions	Yield
With hydrogen; palladium dihydroxide at 20℃; under 760 Torr;	86%

europium trifluoromethanesulfonate + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With sodium chloride In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; ethyl acetate	84%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + yttrium(III) trifluoromethanesulfonate → Tocopherol (59-02-9)

Conditions	Yield
With sodium chloride In diethyl ether; nitromethane; ethyl acetate	82%

(2R,4'R,8'R)-5-(morpholinomethyl)-γ-tocopherol (6991-51-1) + tetrabutylammonium borohydride → n-butyl α-tocopheryl ether + Tocopherol (59-02-9)

Conditions	Yield
In 2-methyl-propan-1-ol for 4h; Heating;	A n/a B 77%

6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-carbaldehyde (113348-75-7) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In acetic acid under 760 Torr;	75%

(2R,6R)-1-chloro-2,6,10-trimethyl-undecane + dilithium tetrachlorocuprate + (2R,6R)-2,6,10-trimethyl-1-undecyl-magnesium chloride + methylmagnesium bromide (75-16-1) + (2S)-(-)-2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol (94353-04-5) → Tocopherol (59-02-9)

Conditions	Yield
In tetrahydrofuran	75%

Durohydroquinone (527-18-4) + 2-methylbut-3-en-2-ol → Tocopherol (59-02-9)

Conditions	Yield
Molecular sieve;	72%

(2RS,6RS)-2,6,10-trimethyl-1-undecylmagnesium chloride + (2RS,6RS)-1-chloro-2,6,10-trimethylundecane + dilithium tetrachlorocuprate + methylmagnesium bromide (75-16-1) + 2-(2-bromoethyl)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran (130266-62-5) → Tocopherol (59-02-9)

Conditions	Yield
In tetrahydrofuran	64%

scandium(III) nitrate + scandium(III) nitrate tetrahydrate + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With sodium chloride In ethyl acetate; toluene	62%

Trimethylhydroquinone (700-13-0) + 2-methylbut-3-en-2-ol → trimethyl-((7R:11R)-trans-phytyl)-benzoquinone-(1.4) (151716-51-7) + Tocopherol (59-02-9)

Conditions	Yield
With CuAl-SBA-15 In cyclohexane at 85℃; for 16h;	A 25% B 61%

ytterbium trifluoromethanesulfonate + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With sodium chloride In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate	59%

hexaethylphosphoric triamide (2283-11-6) + Tocopherol (59-02-9) → bis(N,N-diethylamido)-O-tocopherylphosphite (562828-32-4)

Conditions	Yield
at 90 - 100℃; for 5h;	100%

1,4-dibromo-butane (110-52-1) + Tocopherol (59-02-9) → (R)-6-(4-bromobutoxy)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman (1451385-71-9)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; Inert atmosphere; Darkness;	100%
Stage #1: Tocopherol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	50%
Stage #1: Tocopherol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃;	47%

methanesulfonyl chloride (124-63-0) + Tocopherol (59-02-9) → 2-(4,8,12-trimethyltridecyl)-2,5,7,8-tetramethyl-chroman-6-ylmethanesulfonate (1261156-27-7)

Conditions	Yield
Stage #1: Tocopherol With triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: methanesulfonyl chloride In dichloromethane for 1h;	96%
With pyridine; dmap In dichloromethane at 20℃; for 24h;	85.1%
With pyridine; dmap In dichloromethane at 20℃; for 12h;	85.1%

2,3-O-isopropylidene-4-O-benzyl-α-L-rhamnopyranosyl diphenylphosphate + Tocopherol (59-02-9) → C45H70O6

Conditions	Yield
With C53H57F11N6O4S2 In di-isopropyl ether at 30℃; for 24h; Molecular sieve; Sealed tube; stereoselective reaction;	96%

p-methoxybenzyl chloride (824-94-2) + Tocopherol (59-02-9) → 4-methoxybenzyl (R,R,R)-α-tocopheryl ether (1402580-98-6)

Conditions	Yield
Stage #1: Tocopherol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 20℃;	95%

2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl diphenylphosphate + Tocopherol (59-02-9) → C41H68O7

Conditions	Yield
With C53H57F11N6O4S2 In di-isopropyl ether at 50℃; for 24h; Molecular sieve; Sealed tube; stereoselective reaction;	95%

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + Tocopherol (59-02-9) → (R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 5-bromonicotinate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran Inert atmosphere;	95%

succinic acid anhydride (108-30-5) + Tocopherol (59-02-9) → vitamin E succinate (4345-03-3)

Conditions	Yield
With pyridine; dmap at 25℃;	94%
With sodium hydroxide In butanone at 40℃; for 6h; Reagent/catalyst; Temperature; Solvent;	93.6%
dmap; triethylamine In dichloromethane at 25℃;	85%

2-Bromoacetyl bromide (598-21-0) + Tocopherol (59-02-9) → (R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 2-bromoacetate

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 3h;	93.82%
With pyridine In dichloromethane at 0℃; for 3h;	93.82%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; Sealed tube;	86%
With pyridine In dichloromethane at 20℃; Inert atmosphere;	59%
With pyridine In dichloromethane at 0℃; for 3h;	1 g

N-benzoyl-N-methyl-4-methylbenzenesulfonamide (10533-83-2) + Tocopherol (59-02-9) → (R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl benzoate (102734-34-9)

Conditions	Yield
With potassium phosphate In tetrahydrofuran at 23℃; for 15h; Inert atmosphere; Schlenk technique;	93%

Tocopherol (59-02-9) → 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione (7559-04-8)

Conditions	Yield
With bromine In ethanol at 0 - 20℃; for 1.16667h; pH=6; Mechanism; Solvent; Time; Temperature; pH-value; aq. phosphate buffer;	92%
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 25℃; for 10h;	90%
With iron(III) chloride In methanol; diethyl ether; water for 0.5h;	89%

Upstream product

• 511-72-8 (2R,8aΞ)-8a-ethoxy-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-8aH-chroman-6-one 
• 119-13-1 delta tocopherol 
• 16698-35-4 5,8-dimethyltocol 
• 54-28-4 gamma-tocopherol 
• 50-00-0 formaldehyd 
• 153379-68-1 (R)-tocol acetate 
• 59965-06-9 Vitamin E benzyl ether 
• 69400-39-1 (+) (S)-6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbaldhyde 
• 82299-60-3 Triphenyl-((3R,7R)-3,7,11-trimethyl-dodecylidene)-λ⁵-phosphane 
• 7559-04-8 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 
• 14745-36-9 2-((7R,11R)-3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylbenzene-1,4-diol 
• 130697-13-1 (2R,6R,10R)-1,2-Epoxy-2,6,10,14-tetramethylpentadecan 
• 120680-10-6 (2R,4'R,8'R)-3,4-Didehydro-6-O-(methoxymethyl)-α-tocopherol 
• 34816-26-7 2-methyl-6-phythyl-1,4-benzoquinone 

Downstream Products

• 4345-03-3 vitamin E succinate 
• 102672-59-3 DL-α-tocopherol 4-nitrobenzoate 
• 121656-51-7 (2R,4'R,8'R)-O-(3,5-dinitro-benzoyl)-α-tocopherol 
• 7559-04-8 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 
• 58-95-7 RRR-α-tocopheryl acetate 
• 86362-36-9 DL-α-tocopherol nicotinate 
• 83376-94-7 tocopheroxyl radical 
• 75-65-0 tert-butyl alcohol 
• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 59-02-9 2,5,7,8-Tetramethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ol 
• 2668-47-5 2,6-di(t-butyl)-4-phenylphenol 
• 23531-69-3 C₂₉H₄₉O₂ 
• 87291-70-1 DL-α-Tocopheryl phosphate dianilide 
• 40516-48-1 (13Z)-d-α-tocopherol retinoate 

Relevant articles and documents

FORMATION OF ALPHA TOCOPHEROL FROM 2,3,6-TRIMETHYLPHENOL

The present invention relates to the formation of α-tocopherol from 2,3,6- tri?methyl?phenol comprising the steps a) the oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethylquinone. b) the reduction of 2,3,5-trimethylquinone to 2,3,5-trimethylhydroquinone c) the condensation of 2,3,5-trimethylhydroquinone and isophytol or a phytol derivative in such a manner that all reaction steps a), b) and c) are performed in cyclic alkylene carbonate solvent.

Novel PEGylated derivatives of α-tocopherol for nanocarrier formulations; synthesis, characterization and in vitro cytotoxicity against MCF-7 breast cancer cells

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

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.

SYNTHESIS OF CHROMANOL AND 2-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES

The present invention relates to a process for the production of chromanol and 2-methyl-1,4-naphthoquinone derivatives, more specifically to a process for preparing a compound of the general formula (I) or (II) wherein the variables are as defined in the claims and the description.

Imidazole ionic liquid, preparation method thereof, and application thereof in synthesis of vitamin E acetate

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.

Preparation method for high-purity tocopherol succinate salt

The invention relates to the field of organic synthesis, specifically to a preparation method for tocopherol succinate salt. The preparation method for the tocopherol succinate salt provided by the invention comprises the following steps: hydrogenating dl-alpha-tocopherol in the presence of a precious metal catalyst, subjecting a hydrogenated product and succinic anhydride to an esterification reaction in the presence of alkali so as to prepare a tocopherol succinate intermediate; and subjecting the tocopherol succinate intermediate to salt-forming. The preparation method for the tocopherol succinate salt provided by the invention can effectively improve the purity of a target product, can effectively reduce the content of a single impurity, and can prepare a calcium salt product with a purity capable of reaching 99.9% or above.

COSMETIC COMPOSTION COMRPISING ACTIVE INGREDIENT PRECURSOR AND ENZYME FOR MAINTAIN CONSTANTLY CONCENTRATION OF SKIN ACTIVE SUBSTANCE

PURPOSE: A cosmetic composition containing enzyme and precursor with an activity at low temperature is provided to promoter skin cell activation and to improve anti-wrinkling and elasticity. CONSTITUTION: A cosmetic composition contains an enzyme with an activity at 0°C-15°C and at least one precursor which produces an active ingredient by reaction with the enzyme. The enzyme is hydrolase such as lipase, choline esterase, phosphatase, dioxyribonuclease, carboxypeptidase, pepsin, trypsin, or chemotrypsin. The precursor is retinyl palmitate, tocopheryl acetate, or piceid. The cosmetic composition is used for anti-aging, skin moisturizing, or skin whitening. The active ingredient is retinol, tocopherol, or resveratrol.

Synthesis of 2,2-dialkyl chromanes by intramolecular Ullmann C–O coupling reactions toward the total synthesis of D-α-tocopherol

The complete synthesis of D-α-tocopherol was achieved using our developed-Ullmann C–O coupling reaction as a key reaction. The synthesis of the core structure of D-α-tocopherol, which is a chiral chromane, has never been reported using intramolecular Ullmann C–O coupling reactions owing to the low reactivity of electron-rich iodoarenes with tertiary alcohols. Because the developed intramolecular C–O coupling reactions prefer electron-rich iodoarenes with tertiary alcohols, we successfully synthesized the chiral chromane core and achieved the total synthesis of D-α-tocopherol.

Highly stereoselective construction of the C2 stereocentre of α-tocopherol (Vitamin E) by asymmetric addition of Grignard reagents to ketones

Tertiary alcohol precursors of both C2 diastereoisomers of α-tocopherol were prepared in three ways by our recently reported asymmetric Grignard synthesis. The versatility of Grignard chemistry inherent in its three-way disconnection was exploited to allow the synthesis of three product grades: 77:23 dr (5 steps), 81:19 dr (5 steps) and 96:4 dr (7 steps, one gram scale) from readily available and abundant starting materials. The products were converted to their respective α-tocopherols in 3 steps, which allowed a definitive re-assignment of their absolute configurations.

SEPARATION OF CHIRAL ISOMERS BY SFC

The present invention relates to the field of separating chiral isomers from each other. Particularly, it relates to the field of separating of chiral isomers of chromane or chromene compounds, particularly tocopherols, 3,4-dehydro-tocopherols and tocotrienols, as well as the protected forms thereof. It has been found that the use of supercritical carbon dioxide as mobile phase combined with the very specific chiral phase as stationary phase leads to a very efficient separation of the individual chiral isomers. As the method is very efficient and fast combined with advantageous in view of ecology it is of big industrial interest.