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Vitamin E

(total 76)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
RRR-a-tocopherol d-a-tocopherol
2R-(4'R,8'R,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0001
Fumiko Hirahara
RRR-a-Toc/d-a-Toc
C29H50O2 430.706 Download ChemDraw structure file
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. RRR-a-tocopherol has been reported as 135-194% more than all-rac-a-tocopherol when evaluated by the rat resorption-gestation test , about 200% in terms of tissue retention of deuterated tocopherols in rat and human. The relationship between a-tocopherol and its derivatives was announced by USP.
[Table 0008]
[Table 0009] RRR-a-tocopherol has been assigned an activity of 1 mg a-TE per mg.
[Table 0010] (Ref. 0034/0035/0036)
a5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=+0.32deg in ethanol/d5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=-3.0deg in benzene (Ref. 0001)
practically insol in water , freely sol in acetone, in ethanol, in ether, in methylene chloride and in fatty oils (Ref. 0002)
292nm, E1%1cm=75.8(ethanol)
3310,2930,1620,1590,1460,1375,1270,1160,850cm-1
NMR spectrometry(60 MHz:CDCl3)
[Spectrum 0001] (Ref. 0032)


Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
1.High linoleic acid type margarine 2.Sunflower oil 3.Cottonseed oil 4.Wheat germ 5.Roasted and salted sweet almond 6.Safflower oil 7.Rice bran oil 8.Roasted hazelnuts 9.Dried sunflower seeds 10.Anglerfish liver 11.Roasted Pine nuts 12.Virginia type dried peanuts 13.Spanish type dried peanuts 14.Salted roe 15.Uncooked and salted pollack roe 16.Palm oil 17.Cultured fish 18.Olive oil 19.Fried potato chips 20.Black karinto 21.Age-senbei 22.Raw roe (Ref. 0003/0004/0005/0006/0007/0033/0034)
The positively rotating formylchroman compound is condensed with the C15-phosphonium bromide to give (2S,4'R,8'R)-1',2'-dehydro-a-tocopherol acetate. After catalytic hydrogenation of the double bond and hydrolysis of the acetate grouping, (2R,4'R,8'R)-a-tocopherol is produced.
[Table 0003] (Ref. 0008)
The apparent absorption of RRR-a-tocopherol in human is found to be similar whether administered as the free phenol, the acetyl ester, or the succinyl ester.(Ref. 0044) All-rac-a-tocopherol compared with RRR-a-tocopherol is preferentially metabolized to a-CEHC and excreted.(Ref. 0043)
Ataxia with vitamin E deficiency (AVED), or familial isolated vitamin E deficiency, is a rare autosomal recessive neurodegenerative disease characterized clinically by symptoms with often striking resemblance to those of Friedreich ataxia. (Ref. 0042)

2
2-epi-a-tocopherol
2S-(4'R,8'R,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0002
Fumiko Hirahara
l-a-Toc
C29H50O2 430.706 Download ChemDraw structure file






(2S,4'R,8'R)-a-tocopherol can be conveniently prepared by an alternative procedure starting from (2R,4'R,8'R)-a-tocopherol as follows.
[Table 0001] (Ref. 0008)



3
2-ambo-a-tocopherol
2RS-(4'R,8'R,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0003
Fumiko Hirahara
2-ambo-a-toc
C29H50O2 430.706 Download ChemDraw structure file






(2RS,4'R,8'R)-a-tocopherol was first synthesized from trimethylhydroquinone and 1,3-dibromophythane. Subsequently, a method for condensing phytyl bromide, prepared from natural phytol, with trimethylhydroquinone in petroleum ether with zinc chloride as the catalyst, was reported. This synthesis was also achieved by directly condensing phytol with trimethylhydroquinone. (Ref. 0001) Synthesis of (2RS,4'R,8'R)-a-tocopherol
[Table 0002] (Ref. 0008)



4
all-rac-a-tocopherol
2RS-(4'RS,8'RS,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0004
Fumiko Hirahara
all-rac-a-toc
C29H50O2 430.706 Download ChemDraw structure file
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. RRR-a-tocopherol has been reported as 135-194% more than all-rac-a-tocopherol when evaluated by the rat resorption-gestation test , about 200% in terms of tissue retention of deuterated tocopherols in rat and human. The relationship between a-tocopherol and its derivatives was announced by USP.
[Tables 0008/0009) RRR-a-tocopherol has been assigned an activity of 1 mg a-TE per milligram.
[Table 0010] (Ref. 0034/0035/0036)
practically insol in water , freely sol in acetone, in ethanol, in ether, in methylene chloride and in fatty oils (Ref. 0002)



Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)

(2RS,4'RS,8'RS)-a-tocopherol was synthesized from trimethylhydroquinone and racemic phytol.
[Table 0002] (Ref. 0008)
The apparent absorption of RRR-a-tocopherol in human is found to be similar whether administered as the free phenol, the acetyl ester, or the succinyl ester.(Ref. 0044) All-rac-a-tocopherol compared with RRR-a-tocopherol is preferentially metabolized to a-CEHC and excreted.(Ref. 0044)


5
b-tocopherol
2R-(4R',8R',12'-trimethyltridecyl)-2,5,8-trimethylchroman-6-ol
VVE0005
Fumiko Hirahara
b-Toc
C28H48O2 416.680 Download ChemDraw structure file
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. RRR-b-tocopherol has been reported as 25-40% of RRR-a-tocopherol when evaluated by the rat resorption-gestation test.
[Table 0008] RRR-b-tocopherol has been assigned an activity of 0.5 mg a-TE per milligram.
[Table 0010] (Ref. 0034/0035/0036)
200-210deg(Ref. 0009)
a5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=+2.9(ethanol),+0.9(benzene)deg(Ref. 0001)/dd-20=+6.37deg(Ref. 0009)
Freely soluble in oils, fats, acetone, alcohol, chlororoform, ether, other fat solvents.(Ref. 0009)
296nm, E1%1cm=89.4(ethanol)(Ref. 0001)
3320,2940,1595,1458,1373,1229,1158,860cm-1



Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
1.Wheat germ 2.Sencha Tea 3.Rice bran oil 4.Mixed vegetable oil 5.High linoleic acid type margarine(Ref. 0003/0005/0006/0033/0034)




6
g-tocopherol
2R-(4'R,8'R,12'-trimethyltridecyl)-2,7,8-trimethylchroman-6-ol
VVE0006
Fumiko Hirahara
g-Toc
C28H48O2 416.680 Download ChemDraw structure file
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. RRR-g-tocopherol has been reported as 1-11% of RRR-a-tocopherol when evaluated by the rat resorption-gestation test.
[Table 0008] RRR-g-tocopherol has been assigned an activity of 0.1 mg a-TE per milligram.
[Table 0010] (Ref. 0034/0035/0036)
200-210deg(Ref. 0009)
a5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=+3.2(ethanol),-2.4(benzene)deg(Ref. 0001)dd-20=-2.4deg(alc.)(Ref. 0009)
Freely soluble in oils, fats, acetone, alcohol, chlororoform, ether, other fat solvents.(Ref. 0009)
298nm, E1%1cm=91.4(ethanol)
3310,2930,1613,1460,1375,1220,1143,870cm-1



Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
g-Tocopherol is the major tocopherol in nature and therefore predominates in diet. 1.Soybean oil 2.Corn oil 3.Mixed vegetable oil 4.Mixed salad oil 5.Sesame oil 6.Cottonseed oil 7.Pistachio nuts 8.Walnuts 9. Sesame seeds 10.Skipjack and frigate mackerel canned with oil 11.Pine nuts 12.Kinako 13.High linoleic acid type margarine 14.Brasil nuts 15.Popcorn 16.Tunas canned with oil 17.Peanuts 18.Sencha 19.Milk chocolate 20.Buckwheat flour 21.Hazelnuts 22.Dry cowpeas 23.Rice-kojimiso 24.Raw green soybeans 25.Peanut oil (Ref. 0003/0005/0006/0033/0034)




7
d-tocopherol
2R-(4'R,8'R,12'-trimethyltridecyl)-2,8-dimethylchroman-6-ol
VVE0007
Fumiko Hirahara
d-Toc
C27H46O2 402.653 Download ChemDraw structure file
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. RRR-d-tocopherol has been reported as 1% of RRR-a-tocopherol when evaluated by the rat resorption-gestation test.
[Table 0008] RRR-d-tocopherol has been assigned an activity of 0.03 mg a-TE per milligram.
[Table 0010] (Ref. 0034/0035/0036)
a5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=+3.4(ethanol),+1.1(benzene)deg (Ref. 0001)/d25&546=+3.4deg(alc.)(Ref. 0009)
298nm, E1%1cm=87.3(ethanol)
3360,2915,1605,1460,1375,1210,1145,855cm-1



Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
1.Soybean oil 2.Mixed vegetable oil 3.Kori-dofu 4.Dry cowpea 5.Hard type margarine 6.Soft type margarine 7.Dry azuki-beans 8.Dry soybeans 9.Mixed salad oil 10.kinako 11.Whole egg type mayonnaise 12.High linoleic acid type margarine 13.Egg yolk type mayonnaise 14.Skipjack and frigate mackerel canned with oil 15.Shortening 16.Soybean-koji miso (Ref. 0003/0005/0006/0033/0034)




8 No image
RRS-a-tocopherol
2R-(4'R,8'S,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0008
Fumiko Hirahara
RRS-a-toc
C29H50O2 430.706






H. Mayer and O.Isler's review is recommended to study precisely. (Ref. 0008)



9 No image
RSR-a-tocopherol
2R-(4'S,8'R,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0009
Fumiko Hirahara
RSR-a-toc
C29H50O2 430.706






H. Mayer and O.Isler's review is recommended to study precisely. (Ref. 0008)



10 No image
RSS-a-tocopherol
2R-(4'S,8'S,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0010
Fumiko Hirahara
RSS-a-toc
C29H50O2 430.706






H. Mayer and O.Isler's review is recommended to study precisely. (Ref. 0008)



11 No image
SRS-a-tocopherol
2S-(4'R,8'S,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0011
Fumiko Hirahara
SRS-a-toc
C29H50O2 430.706






H. Mayer and O.Isler's review is recommended to study precisely. (Ref. 0008)



12 No image
SSR-a-tocopherol
2S-(4'S,8'R,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0012
Fumiko Hirahara
SSR-a-toc
C29H50O2 430.706






H. Mayer and O.Isler's review is recommended to study precisely. (Ref. 0008)



13 No image
SSS-a-tocopherol
2S-(4'S,8'S,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0013
Fumiko Hirahara
SSS-a-tocopherol
C29H50O2 430.706






H. Mayer and O.Isler's review is recommended to study precisely. (Ref. 0008)



14
5,7-dimethyltocol
2-(4'R,8'R12'-trimethyltridecyl)-2,5,7-trimethylchroman-6-ol
VVE0014
Fumiko Hirahara
Download ChemDraw structure file

200-220degC/0.05mm
292nm, E1%1cm=83.0(ethanol)
3450,2920,1460,1375,1245,1155,1050 and 855 cm-1 (liquid film)
1H-NMR:6.49,2.59,2.14 and 1.78 ppm




5,7-Dimethyltocol was prepared by the reaction of phytol or isophytol and 2,6-dimethylhydroquinone in the presence of formic acid. (Ref. 0001)



15 No image
7-methyltocol
2-(4'R,8'R,12'-trimethyltridecyl)-2,7-dimethylchroman-6-ol
VVE0015
Fumiko Hirahara

150degC(bath)/10-3mm
298nm, E1%1cm=104.1(ethanol)
3370,2890,1500,1455,1370,1240,1175,1100 and 870 cm-1 (liquid film)









16 No image
5-methyltocol
2-(4'R,8'R,12'-trimethyltridecyl)-2,5-dimethylchroman-6-ol
VVE0016
Fumiko Hirahara

140degC/10-3mm
296nm, E1%1cm=82.4(ethanol)
3440,2915,1460,1380,1285,1155,1065 and 862 cm-1 (liquid film)









17
tocol
2-(4'R,8'R,12'-trimethyltridecyl)-2-methylchroman-6-ol
VVE0017
Fumiko Hirahara
C26H44O2 388.626 Download ChemDraw structure file

b.p..1300.001=165-175deg(Ref. 0010)
298.5nm, E1%1cm=97(ethanol)
3375,2915,1490,1450,1375,1285,1217,1152,1106 and 861 cm-1 (liquid film)





Tocol was obtained by condensing phytol and hydroquinone using formic acids as the catalyst. (Ref. 0001)



18
all-trans-a-tocotrienol
2-(4',8',12'-trimethyltrideca-3',7',11'-trienyl)-2,5,7,8-tetramethylchroman-6-ol
VVE0018
Fumiko Hirahara
a-T3
C29H44O2 424.658 Download ChemDraw structure file
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. all-trans-a-tocotrienol has been reported as 29% of RRR-a-tocopherol when evaluated by the rat resorption-gestation test.
[Table 0008] all-trans-a-tocotrienol has been assigned an activity of 0.3 mg a-TE per milligram.
[Table 0010] (Ref. 0034/0035/0036)
m.p.30-31degC
290 nm, E1%1cm=77.2(ethanol)
3420,1435,1368,1242,1155,1075,917 and 851 cm-1
1H-NMR:d 5.12,4.15,2.58,2.10-1.58 and 1.23 ppm, NMR Spectrum of all-trans-a-Tocotrienol(60 MHz:CDCl3)
[Spectrum 0001] (Ref. 0032)


Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
1.Cococa butter 2.Coconut 3.Palm 4.Palm Oil 5.Rice bran (Ref. 0033/0034)




19
b-tocotrienol
2-(4',8',12'-trimethyltrideca-3',7',11'-trienyl)-2,5,8-trimethylchroman-6-ol
VVE0019
Fumiko Hirahara
b-T3
C28H42O2 410.632 Download ChemDraw structure file
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. all-trans-b-tocotrienol has been reported as 5% of RRR-a-tocopherol when evaluated by the rat resorption-gestation test.
[Table 0008] all-trans-b-tocotrienol has been assigned an activity of 0.05 mg a-TE per milligram.
[Table 0010] (Ref. 0034/0035/0036)
230degC(bath)/0.05mm
295 nm, E1%1cm=85.0(ethanol)
3370,1592,1439,1404,1370,1220,1153,1091,1053,997,847 and 691 cm-1
1H-NMR: 6.45,5.12,4.38,2.62,2.08-1.62,1.25 ppm NMR Spectrum of b-Tocotrienol(60 MHz:CDCl3)
[Spectrum 0001] (Ref. 0032)


Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
1.Barley 2.Wheat Germ (Ref. 0034)




20
g-tocotrienol
2-(4',8',12'-trimethyltrideca-3',7',11'-trienyl)-2,7,8-trimethylchroman-6-ol
VVE0020
Fumiko Hirahara
g-T3
C28H42O2 410.632 Download ChemDraw structure file

296 nm, E1%1cm=91(ethanol)
3440,1667 and 1618 cm-1
1H-NMR: 6.35,5.13,4.28,2.68,2.12-2.02,1.68-1.62 and 1.25 ppm
M=410

Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
1.Palm 2.Palm Oil 3.Rice bran (Ref. 0033/0034)




21
d-tocotrienol
2-(4',8',12'-trimethyltrideca-3',7',11'-trienyl)-2,8-dimethylchroman-6-ol
VVE0021
Fumiko Hirahara
d-T3
C27H40O2 396.605 Download ChemDraw structure file




Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
1.Palm 2.Palm Oil (Ref. 0033/0034)




22 No image
2-(4',8',12'-trimethyltrideca-3',7',11'-trienyl)-2-methylchroman-6-ol
VVE0022
Fumiko Hirahara










23
1-aza-a-tocopherol
6-hydroxy-2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-1,2,3,4-tetrahydroquinoline
VVE0023
Fumiko Hirahara
Download ChemDraw structure file

210degC/0.02mm
240 and 301nm;E1%1cm=164 and 70(ethanol)
3330,1600,1580,1439,1368,1245,1200,1121,1073,1002,962,760cm-1
1H-NMR:4.07,3.20,2.63,2.13,2.03,1.70,1.35,1.22,0.97,0.77 ppm








24 No image
VVE0024
Fumiko Hirahara

1H-NMR:d(CDCl3) 0.79-1.73,1.50,2.09,2.10,2.13,280,2.9513C-NMR:d(CDCl3) 151.7,147.0,123.5,123.2,119.3,115.4
m/e:416,191,165







25 No image
3,4-dehydro-a-tocopherol
2-(4',8',12'-trimethyltridecyl)-2,5,7,8-tetramethyl-3,4-dehydrochroman-6-ol
VVE0025
Fumiko Hirahara

130Cdeg(bath)/0.015mm
235,273,283 and 339nm(e=19100,8300,7400 and 3200)









26
Trolox
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
VVE0026
Fumiko Hirahara
Download ChemDraw structure file

m.p.190-192









27 No image
a-tocopherthiol
2-(4',8',12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-thiol
VVE0027
Fumiko Hirahara

190-200degC/0.005mm
241 and 289nm; E1%1cm=184 and 33 (ethanol)
1H-NMR(CDCl3): 2.85,2.62(t,J=7Hz),2.36,2.32,2.13,1.77(t),1.50,1.23,0.90,0.88 and 0.83 ppm
m/e=446



Condensation of 2,3,5-methylphenol with isophytol and zinc chloride in formic acid yields 6-deoxy-a-tocopherol. Subsequent reduction with zinc in methanolic hydrogen chloride leads to a-tocopherthiol. (Ref. 0001)



28 No image
2,2,5,7,8-pentamethylchroman-6-ol
VVE0028
Fumiko Hirahara










29 No image
2,2,5,8-tetramethylchroman-6-ol
VVE0029
Fumiko Hirahara










30 No image
2,2,7,8-tetramethylchroman-6-ol
VVE0030
Fumiko Hirahara










31 No image
2,2,8-trimethylchroman-6-ol
VVE0031
Fumiko Hirahara
C29H50O2 430.706










32
a-tocopherolquinone
6-(3-hydroxy-3,7,11,15-tetramethylhexadecanyl)-2,3,5-trimethyl-1,4-benzoquinone
VVE0032
Fumiko Hirahara
C29H50O2 430.706 Download ChemDraw structure file






Synthesis of a-Tocopherol Quinone [FT0004] (Ref. 0013)



33
d-a-tocomonenol
2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltrideca-11'-enyl)-6-chroman-6-ol
VVE0033
Fumiko Hirahara
d-a-tocomonenol
Download ChemDraw structure file

UVmax(Ethanol)=292 nm, E1%1cm(284nm)=44.5
[Spectra 0002] (Ref. 0012)
JMN-GX 400 NMR by dissolving d-a-tocomonoenol in CDCl3 [[SP003] (Ref. 0012)
JMX-DX 300 mass spectrometer ; m/e 428: molecular ion peak [[SP004] (Ref. 0012)

HPLC
HPLC condition1: column, Zorbax SIL(5mm, 250mmX4.6mm, Du Pont); mobile phase, n-hexane:dioxane:2-propanol=985:10:5); temperature, 30 deg; flow rate, 1.5 mL/min; Ex 290nm; Em 330nm/HPLC condition2: column, Inertsil(5mm, 250mmX4.6mm, Du Pont); mobile phase, methanol:water=95:5); temperature, 30 deg; flow rate, 1.0 mL/min; Ex 290nm; Em 330nm
[Chromatogram 0001] (Ref. 0012)
palm oil/rice bran oil(Ref. 0012)




34 No image
5R-hydroxy-2R-(4'R,8'R,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6(5H)-one
VVE0034
Fumiko Hirahara










35
d-a-tocopherol acetate/d-a-tocopheryl acetate/RRR-a-tocopheryl acetate/Vitamin E acetate
[2R-[2R(4R,8R)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol acetate
VVE0035
Koichi Abe
d-a-toc ace
C31H52O3 472.743 Download ChemDraw structure file
RRR-a-tocopherol acetate activity was announced as 1.36 IU/mg by USP.
[Table 0009] (Ref. 0035/0036)
ad-25=+0.25deg in chloroform(Ref. 0014)/ad-25=+3.2deg in ethanol(Ref. 0014)/specific optical rotation after de-esterification and oxidation to the quinone
Practically insoluble in water /Soluble in alcohol/ Freely soluble in acetone, ethanol, ether and fatty oils(Ref. 0002)






RRR-a-tocopherol acetate is broken down in gastrointestinal tract, resulting in absorption of a-tocopherol.(Ref. 0037)The apparent absorption of RRR-a-tocopherol in human is found to be similar whether administered as the free phenol, the acetyl ester, or the succinyl ester.(Ref. 0044) All-rac-a-tocopherol compared with RRR-a-tocopherol is preferentially metabolized to a-CEHC and excreted.(Ref. 0043)


36 No image
l-a-tocopherol acetate/l-a-tocopheryl acetate/Vitamin E acetate
[2S-[2R*(4R*,8R*)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol acetate
VVE0036
Koichi Abe
l-a-toc ace
C31H52O3 472.743

ad-25=-2.0deg in ethanol(Ref. 0014)
Practically insoli n water /Freely sol in acetone, chloroform, ether/Less readily sol in alc.






l-a-tocopherol acetate is broken down in gastrointestinal tract, resulting in absorption of a-tocopherol.


37
dl-a-tocopherol acetate/dl-a-tocopheryl acetate/Vitamin E acetate
[2RS-[2RS(4RS,8RS)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol acetate
VVE0037
Koichi Abe
dl-a-toc ace
C31H52O3 472.743 Download ChemDraw structure file
all-rac-a-tocopherol acetate activity was announced as 1.0 IU/mg by USP.
[Table 0009] all-rac-a-tocopherol acetate has been assigned an activity of 0.74 mg a-TE per milligram.
[Table 0010] (Ref. 0035/0036)
-27.5deg(Ref. 0018)
bp0.01=184deg(Ref. 0014)/bp0.025=184deg(Ref. 0014)/bp0.01=184deg(Ref. 0014)
d21.3&4=0.9533(Ref. 0014)/d20&20=0.952-0.966(Ref. 0017)
nd-20=1.4950-1.4972(Ref. 0014)/1.494-1.499(Ref. 0017)
optically inactive(Ref. 0017)
Practically insol in water /Freely sol in acetone, chloroform, ether/Less readily sol in alc (Ref. 0001)
UVmax(cyclohexane)=285.5 nm(Ref. 0015)/UVmax(Ethanol)=285.5 nm(Ref. 0016)E1%&1cm(284nm)=44.5(Ref. 0016)/U=2.24X10312.411 mg of dl-a- tocopheryl acetate per 100ml of cyclohexane;
[Spectrum 0005] (Ref. 0018)
Perkin-Elmer 621 Spectrometer on a capillary layer of the liquid between KBr discs ;2943 and 2861(cm-1): CH3 stretching vibrations, 2920 and 2850(cm-1): CH2 stretching vibrations, 1752(cm-1): C=O stretching vibrations, 1456(cm-1): CH2 and CH3 deformations,1363(cm-1): CH3 symmetric defamations,1263(cm-1): C-O-C stretching vibrations
[Spectrum 0006] (Ref. 0018)
Jeolco 60 MHz NMR by dissolving 92.4 mg of dl-a-tocopheryl acetate in 0.5 ml of CDCl3 containing tetramethylsilane as an internal reference;
[Spectrum 0007] (Ref. 0018)
CEC 21-110 mass spectrometer with an ionizing energy of 70 eV; m/e 472: molecular ion peak, m/e 430: the loss of ketene from the molecular ion
[Spectrum 0008] (Ref. 0018)

TLC Plate;Silica Gel G plate, Developing Solvent; cyclohexane : ethyl ether(4: 1) Rf=0.7
GLC Column;5-10% SE-30 Silanized Diatomaceous Earth in Pyrex, Column Temperature; 280deg, Carrier: N2 gas ca.40ml/min , retention Time; 26min (Ref. 0018)

dl-a-tocopherol is dissolved in acetic anhydride and heated to 140deg. The solution is then taken up in petroleum ether, the solvents are removed in vacuo at 80deg, and the residue is distilled under high vacuum at 200-210deg.(Ref. 0008)
All-rac-a-tocopherol acetate is almost completely hydrolyzed prior to absorption, probably by a duodenal mucosal esterase and free a-tocopherol is then further metabolized to a-tocopherol quinine, a-tocopherol diver, a-tocopheronic acid and CEHC. When larger doses are administered, high blood levels are attained with tocopherol than with tocopheryl acetate administration.
[Table 0004] (Ref. 0018/0019/0027/0037) The apparent absorption of RRR-a-tocopherol in human is found to be similar whether administered as the free phenol, the acetyl ester, or the succinyl ester.(Ref. 0044) All-rac-a-tocopherol compared with RRR-a-tocopherol is preferentially metabolized to a-CEHC and excreted.(Ref. 0043)


38
d-a-tocopherol succinate/d-a-tocopheryl succinate/RRR-a-tocopheryl hydrogen succinate/d-a-tocopheryl acid succinate/Vitamin E succinate/Vitamin E acid succinate
[2R-[2R(4R,8R)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol succinate
VVE0038
Koichi Abe
d-a-toc suc
C33H54O5 530.779 Download ChemDraw structure file
RRR-a-tocopherol succinate activity was announced as 1.21 IU/mg by USP.
[Table 0009] (Ref. 0035/0036)
76-77deg(Ref. 0020)
a5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=+4.4deg in ethanol/d5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=+2.6deg in benzene(Ref. 0020)
Practically insol in water / sol in acetone, ethanol, ether/very soluble in methylene chloride(Ref. 0021)
UVmax(ethanol)= 286nm/E1%1cm(284nm)=38.5(Ref. 0021)





An a-tocopherol concentrate was heated with succinic anhydride in pyridine. The mixture was diluted with ethyl ether and was allowed to stand at 3 deg. Succinic anhydrides were well washed with ethyl ether. The filtrate, further diluted with ether, was washed with hydrochloric acid, wasted and dried. After distillation of ether a dark oily residue was obtained. This was dissolved in petroleum ether and adsorbed on a mixture of Special Filtrol and Hyflo Super Cel in an adsorbent column . The solution was forced through the column under nitrogen pressure. The column was washed with petroleum ether , then the strongly adsorbed a-tocopherol succinate was eluted with ethyl ether and recrystallized from a 10% solution in petroleum ether.(Ref. 0020)
d-a-tocopherol succinate is broken down in gastrointestinal tract, resulting in absorption of a-tocopherol. The apparent absorption of RRR-a-tocopherol in human is found to be similar whether administered as the free phenol, the acetyl ester, or the succinyl ester.(Ref. 0044)


39 No image
l-a-tocopherol succinate/l-a-tocopheryl succinate/l-a-tocopheryl acid succinate/Vitamin E succinate/Vitamin E acid succinate
[2S-[2R*(4R*,8R*)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol succinate
VVE0039
Koichi Abe
l-a-toc suc
C33H54O5 530.779







l-a-tocopherol succinate is broken down in gastrointestinal tract, resulting in absorption of a-tocopherol.


40
dl-a-tocopherol succinate/dl-a-tocopheryl succinate/dl-a-tocopheryl acid succinate/Vitamin E succinate/Vitamin E acid succinate
[2RS-[2RS(4RS,8RS)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol succinate
VVE0040
Koichi Abe
dl-a-toc suc
C33H54O5 530.779 Download ChemDraw structure file

76-77deg(Ref. 0022)
ad-25=-0.001-+0.001deg in ethanol(Ref. 0022)
Practically insol in water (Ref. 0022)/ sol in acetone, ethanol, ether/very soluble in methylene chloride
UVmax(ethanol)= 286nm(Ref. 0022)



GLC Column;5-10% SE-30 Silanized Diatomaceous Earth in Pyrex, Column Temperature; 280deg, Carrier: N2 gas ca.40ml/min , retention Time; 23min (Ref. 0018)


RRR-a-tocopherol succinate is broken down in gastrointestinal tract, resulting in absorption of a-tocopherol. The apparent absorption of RRR-a-tocopherol in human is found to be similar whether administered as the free phenol, the acetyl ester, or the succinyl ester.(Ref. 0044)


41 No image
d-a-tocopherol nicotinate/d-a-tocopheryl nicotinate/Vitamin E nicotinate
[2R-[2R(4R,8R)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol nicotinate
VVE0041
Koichi Abe
d-a-toc nic
C35H53NO3 535.800

UVmax(ethanol)= 263-265 nm






d-a-tocopherol nicotinate may be broken down in gastrointestinal tract, resulting in absorption of a-tocopherol.


42 No image
l-a-tocopherol nicotinate/l-a-tocopheryl nicotinate/Vitamin E nicotinate
[2S-[2R*(4R*,8R*)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol nicotinate
VVE0042
Koichi Abe
l-a-toc nic
C35H53NO3 535.800

UVmax(ethanol)= 263-265 nm






l-a-tocopherol nicotinate may be partially broken down in gastrointestinal tract, resulting in absorption of a-tocopherol.


43
dl-a-tocopherol nicotinate/l-a-tocopheryl nicotinate/Vitamin E nicotinate
[2RS-[2RS(4RS,8RS)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol nicotinate
VVE0043
Koichi Abe
dl-a-toc nic
C35H53NO3 535.800 Download ChemDraw structure file

about 38deg
very sol in acetone, ethanol, ether/freely soluble in ethanol/practically insol i water.(Ref. 0024)
UVmax(ethanol)= 263-265 nm






dl-a-tocopherol nicotinate is partially hydrolysed in gastrointestinal tract, resulting in absorption of a-tocopherol.


44
dl-a-tocopherol succinate Ca/dl-a-tocopheryl succinate Ca/dl-a-tocopheryl acid succinate Ca/Vitamin E succinate Ca/Vitamin E acid succinate Ca
[2RS-[2RS(4RS,8RS)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol succinate monocalcium salt
VVE0044
Koichi Abe
dl-a-toc suc Ca
C33H54O5 530.779 Download ChemDraw structure file

Optically inactive(Ref. 0025)
Freely soluble in chloroform, carbon tetrachloride/Practically insoluble in water, ethanol , acetone (Ref. 0025)
UVmax(chloroform)= 286 nm (Ref. 0025) /E1%1cm(284nm)=36.0-40.0(chloroform)






d-a-tocopherol succinate calcium is broken down in gastrointestinal tract, resulting in absorption of a-tocopherol.


45
DL-a-tocopheryl retinoate/Tocoretinate
2RS-2,5,7,8-tetramethyl-2-[(4RS,8RS)-4,8,12-trimethyltridecyl]-6-chromanyl retinoate
VVE0045
Koichi Abe
C49H76O3 713.126 Download ChemDraw structure file

UVmax(ethanol)= 365nm/E1%1cm(365nm)=642(Ref. 0040)









46
2-(a-D-glucopyranosyl)-2,5,7,8-teramethylchroman-6-ol
VVE0046
Koichi Abe
TMG
C20H30O8 398.447 Download ChemDraw structure file
Antioxidant Activity (Ref. 0001/0002)
freely soluble in water(Ref. 0028)
UVmax(ethanol)= 291nm(Ref. 0028)
3400,2920,1640,1460,1420,1380,1260,1150,1110,1030 and 920 cm-1(Ref. 0028)
13C NMR Spectra
[Table 0006] (Ref. 0028)
m/Z; 398(M+), 237,219, 205,191,165 (fragment ion) (Ref. 0028)

Reversed-phase HPLC chromatogram
[Chromatogram 0004] (Ref. 0028)

The procedure of TMG Synthesis
[Table 0005]



47
Phosphatidylchromanol
1,2-dimyristoyl-sn-glycero-3-phospho-2'-hydrxyethyl-2',5',7',8'-tetramethyl-6'-hydroxychroman
VVE0047
Koichi Abe
PCh
Download ChemDraw structure file
Antioxidant Activity (Ref. 0001)
13C NMR Spectra of PCh
[Table 0007] (Ref. 0030)
M+H+=825 (Ref. 0030)







48
2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman
VVE0048
Koichi Abe
LLU-a
C12H18O4 226.269 Download ChemDraw structure file
Natriuretic Factor(Ref. 0001)
147-148degC
UVmax(ethanol)= 205 and 294nm
[Spectrum 0009] (Ref. 0026)
1H and 13C NMR Spectra
[Spectrum 0010] (Ref. 0026)

Chromatogram of LLU-a
[Chromatogram 0002] (Ref. 0026)





49
a-carboxyethyl-6-Hydroxychroman
2,5,7,8-tetramethyl-2(2'-carboxyethyl)-6-hydroxychroman
VVE0049
Koichi Abe
a-CEHC/5-Me-LLU-a
Download ChemDraw structure file

UVmax= 210 and 290nm
[Spectrum 0011] (Ref. 0027)



HPLC chromatograms: Column; LiChrospher RP 8, Mobile phase; a Gradient of acetonitrile-McIlvain buffer, detection;210nm with the diode array
[Chromatogram 0001]
Gas chromatograms: column; a fused silica DB-MS capillary column, temperature;180-280deg (10deg/min, 20min isothermic)
[Chromatogram 0003] (Ref. 0027)





50
Raxofelast
5-(acetyloxy)-2,3-dihydro-4,6,7-trimethyl-2-benzofuran acetic acid
VVE0050
Koichi Abe
IRFI-016
Download ChemDraw structure file










51
dl-a-tocopherol linoleate
[2RS-[2RS(4RS,8RS)] ]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol linoleate
VVE0051
Koichi Abe
C47H80O3 693.136 Download ChemDraw structure file

d2020=0.930-0.942(Ref. 0045)
n20D=1.495-1.449(Ref. 0045)
E1%1cm(286nm)=31-40(0.01g,hexane,100ml)(Ref. 0045)









52
Troglitazone
5-[ [4-[(3,4-Dihydro-6-hydroxy-2,5-7,8-tetramethyl-2H-1-benzopyran-2-y)methoxy]phenyl]methyl]-2,4-thiazolidine
VVE0052
Koichi Abe
C24H27NO5S 441.541 Download ChemDraw structure file
Anti diabetic.
mp=184-186deg(Ref. 0046)









53
a-tocopherol quinone/a-tocopheryl quinone
2-(3-hydroxy-4,8,12-trimethyltridecyl)-3,5,6-trimethylbenzoquinone
VVE0053
Koichi Abe
a-TQ
C29H50O2 430.706 Download ChemDraw structure file

lmax=269nm, loge=4.21 (Ref. 0047)
C=Ostretch of quinone=1641 cm-1(Ref. 0047)





a-tocopherol is oxidized by ferric chloride, silver nitrate or chloro-auric acid to a-tocopherylquinone.(Ref. 0055)



54
2,8-dimethyl-2(2'-carboxyethyl)-6-hydroxychroman
VVE0054
Koichi Abe
d-CEHC
C14H18O4 250.290 Download ChemDraw structure file

IR spectrum of d-CEHC methyl ester (Ref. 0048)
NMR spectrum of d-CEHC methyl ester (Ref. 0048)
MS spectrum of methylated and reductive acetylated derivative of d-CEHC
[Spectrum 0013] (Ref. 0048)



To a mixture of 2-methyl-1,4-benzohydroquinone-4-benzoate, dioxane and BF3-ether, a solution of g-vinyl-g-valerolactone in dioxane was added drop wise. The reaction mixture was extracted with ether. The extract was hydrolyzed, diluted with water and extracted with ethyl acetate. The extracted residue was chromatographed and then recrystallized.



55
g-tocopherol quinone/g-tocopheryl quinone
2-(3-hydroxy-4,8,12-trimethyltridecyl)-5,6-dimethylbenzoquinone
VVE0055
Koichi Abe
g-TQ
C28H48O2 416.680 Download ChemDraw structure file






g-tocopherol is oxidized by ferric chloride to a-tocopherylquinone.(Ref. 0055)



56
d-tocopherol quinone/d-tocopheryl quinone
2-(3-hydroxy-4,8,12-trimethyltridecyl)-6-methylbenzoquinone
VVE0056
Koichi Abe
d-TQ
C27H4602 4962.829 Download ChemDraw structure file










57
2,2,5,7,8-Pentamethyl-6-hydroxychroman
VVE0057
Koichi Abe
PMC
C14H20O2 220.307 Download ChemDraw structure file
PMC inhibits induction of nitric oxide synthase by bacterial Lipopolysaccharide. (Ref. 0056)









58
L-Ascorbic acid 2-[3,4-dihydro-2,5,7,8-tetramathyl-2-(4,8,12-trimethyltridecyl)-2-1-benzopyran-6-yl hydrogen phosphate] potassium salt
VVE0058
Koichi Abe
EPC-K1
C35H56O16PK 802.882 Download ChemDraw structure file

sol in water ,Less readily sol in methanol, practically insol in acetone, in ethyl acetate, in ether, in chloroform









59
2,3-dihydro-5-hydroxy-2,2-dipentyl-4,6,-dii-tert-butylbenzofuran
VVE0059
Koichi Abe
BO-653
C26H44O2 388.626 Download ChemDraw structure file
radical scavenging action.









60
[2R-[2R(4R,8R)] ]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol palmitate
VVE0060
Koichi Abe
d-alpha-Toc palmitate
C45H80O3 669.115 Download ChemDraw structure file

42-43deg(Ref. 0057)
UVmax=280nm, E1%1cm=30.9(Ref. 0057)









61
[2RS-[2RS(4SR,8SR)] ]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol palmitate
VVE0061
Koichi Abe
dl-alpha-palmitate
C45H80O3 669.115 Download ChemDraw structure file

36-38deg(Ref. 0057)
UVmax=286nm, E1%1cm=36.8(Ref. 0057)









62
the (-) enantiomer of the racemate U-78517F
[2-[4-[2,6-di-(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]methyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol, dihydrochloride
VVE0062
Koichi Abe
U-83836-E
C30H46O2N6Cl2 593.631 Download ChemDraw structure file










63
RRR-a-tocopheryl polyethylene glycol succinate/Tocophersolan
Poly(oxy-1,2-ethanediyl), a-[4-[[3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridcyl)-2H-1-benzopyran-6-yl]oxy]-1,4-dioxobutyl-w-hydroxy-
VVE0063
Koichi Abe
TPGS
Download ChemDraw structure file










64
2-(3-chloropropyl)-2,5,7,8-tetramethyl-6-chromanol
VVE0064
Koichi Abe
C16H23ClO2 282.805 Download ChemDraw structure file

1H-NMR(CDCl3) d:4.20(1H,s), 3.53(2H,t,J=6.4Hz), 2.61(2H,t,J=6.7Hz), 2.46-2.21(2H,m), 2.13, 2.10(9H,s), 2.05-1.63(4H,m), 1.25(3H,s)(Ref. 0051)
m/z: 282(M+)(Ref. 0051)







65
2R,4R,8R-2,4,6,7-tetramethyl-2-(4,8,12-trimethyl-2-(4,8,12-trimethyltridecyl)-5-hydroxy-3,4-dihydrobenzofuran
VVE0065
Koichi Abe
C28H4802 5176.427 Download ChemDraw structure file










66
dl-a-Tocpheryl p-nitrobenzoate
[2RS-[2RS(4SR,8SR)] ]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecey)-2H-1-benzopyran-6-ol p-nitrobenzoate
VVE0066
Koichi Abe
C36H53O5N
Download ChemDraw structure file

46-47deg(Ref. 0057)









67
spirodienone ether dimer
VVE0067
Koichi Abe
Download ChemDraw structure file

E(1%,1cm)(300nm)=53.8(Ref. 0053), E(1%,1cm)(299nm)=95(Ref. 0054)
5.97, 6.03 and 6.27m(carbonyl and conjugated double bonds), 7.96, 9.13, 10.36m(ether) (Ref. 0053)









68
a-tocopheronic acid
2-(3-hydroxy-3-methyl-5-carboxypentyl)-3,5,6-trimethylbennzoquinone
VVE0068
Koichi Abe
C16H2205 2414.679 Download ChemDraw structure file

IR spectra of a-tocopheronic acid, its g-lactone and hydroquinone diacetate(Ref. 0049)









69
N-Methyl-2,2,7,8-tetramethyl-6-amino-chromane
VVE0069
Koichi Abe
N-Me-Me4-C
C14H20ON 218.315 Download ChemDraw structure file

IR spectrum of N-Me-Me4-C[SP] (Ref. 0052)
NMR spectrum of N-Me-Me4-C[SP] (Ref. 0052)








70
5-Nitro-g-tocopherol
2R-(4'R,8'R,12'-trimethyltridecyl)-5-nitro-2,7,8-trimethyl-chroman-6-ol
VVE0070
Koichi Abe
5-NO2-gT
C26H4704N 5067.635 Download ChemDraw structure file










71
Tocored
2RS-(4'RS,8'RS,12'-trimethyltridecyl)-2,7,8-trimethylchroman-5,6-quinone
VVE0071
Koichi Abe
C28H46O3 430.663 Download ChemDraw structure file

UVmax=257,261nm(Ref. 0055)





When g-tocopherol is oxidized with ferric chloride in the absence of aa'-dipyridyl, tocored is obtained.(Ref. 0055)



72
b-tocopherol quinone
2-(3-hydroxy-4,8,12-trimethyltridecyl)-3,6-dimethylbenzoquinone
VVE0072
Koichi Abe
b-TQ
C28H48O2 416.680 Download ChemDraw structure file

C=O stretch of quinone=1649 cm-1, C=C of quinone ring= 1617cm-1(Ref. 0047)





b-tocopherol is oxidized by silver nitrate or ferric chloride to b-tocopherylquinone.(Ref. 0055)



73
2-(2',5',7',8'-tetramethyl-6'-hydroxychromanyl)ethylphosphate
VVE0073
Koichi Abe
Ch-P
C15H22O6P 329.305 Download ChemDraw structure file

UVmax=290nm, u=2800(Ref. 0050)
1H-NMR Chemical shifts of Ch-P(Ref. 0050)








74
3,4-dihydro-6-hydroxy-N,N,N-2,5,7,8-heptamethyl-2H-1-benzppyran-2-ethanaminium 4-methylbenzenesulfonate
VVE0074
Koichi Abe
MDL 73404
C18H30O2N 292.436 Download ChemDraw structure file
MDL 73404 is at least 40 tomes more potent inhibitors of Fe-driven heart microsomal lipid peroxidation than Trolox. (Ref. 0058)









75
3-Hydroxy-5-(1,2-dihydroxyethyl)-4-[6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-chroman-5-ylmethoxy]-furan-2(5H)-one
VVE0075
Koichi Abe
Tocpheryl Ascorbate
C35H56O8 604.814 Download ChemDraw structure file






Synthesis of 5a-Tocopheroyl Ascorbate
[Table 0005] (Ref. 0059)



76
marine-derived tocopherol
3,4-dihydro-2,5,7,8-tetramethyl- 2 - (4,8,12-trimethyl-12-tridecenyl) -2H-1-benzopyran-6-ol
VVE0076
Koichi Abe
MDT
C29H48O2 428.690 Download ChemDraw structure file

1H NMR 1.99m of MDT [SP0012], 13C NMR Spectrum of MDT
[Spectrum 0013] (Ref. 0060)
Mass Spectrum of MDT
[Spectrum 0014] (Ref. 0060)

HPLC retention time; MDT=10.1min, a-tcopherol=12.3min ( Column; Spelco LC-18, Mobile phase; 50 mM NaClO4 in methanol, Flow Rate; 1 ml/min)






Reference
[0001]
AUTHOR:Kasparek,S.(1980)Chemistry of Tocopherols and Tocotrienols, in Vitamin E, a comprehensive Treasure (Machlin, L.J. ,eds.), PP7-65, Marcel Dekker, INC., New York and Basel
TITLE:
JOURNAL:
VOL: PAGE : - ()

[0002]
AUTHOR:RRR-a-tocopherol,all-rac-a-tocopherol(1998), in European Pharmacopoeia-Supplement (Council of Europe eds.) , pp486-489
TITLE:
JOURNAL:
VOL: PAGE : - ()

[0003]
AUTHOR:Standard Tables of Fat-soluble Food Composition in Japan (1995) Fatty Acid,Cholesterol,Vitamin E( the Science and Technology Agency,eds),,pp13-103, Ishiyaku Press Ltd. (Japan),Tokyo
TITLE:
JOURNAL:
VOL: PAGE : - ()

[0004]
AUTHOR:Sheppard, A.J., Pennington,A.T.(1993) Analysis and Distribution of Vitamin E in Vegetable Oils and Foods, in Vitamin E in Health and Disease (Packer, L. , Fuchs, J. eds.),pp9-31,Marcel Dekker Inc , New York
TITLE:
JOURNAL:
VOL: PAGE : - ()

[0005]
AUTHOR:Goh S. H. , Choo, Y. M. and Ong, S. H.
TITLE:
JOURNAL:J. Amer. Oil Chem. Soc.
VOL:62 PAGE : 237-240 (1985)

[0006]
AUTHOR:Leth, T., and Sondergaard, H.
TITLE:Biological activity of vitamin E compounds and natural materials by the resorption-gestation test, and chemical determination of the vitamin E activity in foods and feeds PubMed ID:925769
JOURNAL:J Nutr.
VOL:107 PAGE : 2236-2243 (1977)

[0007]
AUTHOR:Evans H.M., Emerson,O.H. and Emerson,G.A.
TITLE:The Isolation from Wheat Germ Oil of an Alcohol, a-Tocopherol, having the Properties of Vitamin E.
JOURNAL:J. Biol. Chem.
VOL:113 PAGE : 319-332 (1936)

[0008]
AUTHOR:Isler, O., Mayer,H.(1971) [227]Synthesis of Vitamin E , in Methods in Enzymnology vol.18 (McCormick, D,B.,Wright,L. D eds.),pp241-348, Academic Press, New York and London
TITLE:
JOURNAL:
VOL: PAGE : - ()

[0009]
AUTHOR:Tocopherol(1996), in The Merck Index (Twelfth Edition), pp1620, Merck & Co., Inc.
TITLE:
JOURNAL:
VOL: PAGE : - ()

[0010]
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