Record Information
public_id FDB002432
Chemical Information
name d-Tocopherol
description Widespread occurrence in vegetable oils incl. soya and sunflower oils. Used as antioxidant food additive. Member of Vitamin E group. Added to fats and oils to prevent rancidity. The naturally occurring tocopherol is a single stereoisomer; synthetic forms are a mixt. of all eight possible isomers 1 IU of tocopherol is defined as ? milligrams of RRR-alpha-tocopherol (formerly named d-alpha-tocopherol or sometimes ddd-alpha-tocopherol). 1 IU is also defined as 1 milligram of an equal mix of the eight stereoisomers, which is a racemic mixture called all-rac-alpha-tocopheryl acetate. This mix of stereoisomers is often called dl-alpha-tocopheryl acetate, even though it is more precisely dl,dl,dl-alpha-tocopheryl acetate). However, 1 IU of this racemic mixture is not now considered equivalent to 1 IU of natural (RRR) ?-tocopherol, and the Institute of Medicine and the USDA now convert IU's of the racemic mixture to milligrams of equivalent RRR using 1 IU racemic mixture = 0.45 "milligrams ?-tocopherol".; A cataract is a condition of clouding of the tissue of the lens of the eye. They increase the risk of disability and blindness in aging adults. Antioxidants are being studied to determine whether they can help prevent or delay cataract growth. Observational studies have found that lens clarity, which is used to diagnose cataracts, was better in regular users of vitamin E supplements and in persons with higher blood levels of vitamin E. A study of middle aged male smokers, however, did not demonstrate any effect from vitamin E supplements on the incidence of cataract formation. The effects of smoking, a major risk factor for developing cataracts, may have overridden any potential benefit from the vitamin E, but the conflicting results also indicate a need for further studies before researchers can confidently recommend extra vitamin E for the prevention of cataracts. It is important to note that the term "cataract" may be used in common parlance for an opacity involving any tissue of the eye, for example a corneal scar. Thus a character in theater or on television who is blind from cataracts might have white instead of clear corneas, covering over the iris and pupil. Since the lens is behind the pupil, real cataracts are difficult to see without special instrumentation, so people with cataracts have rather normally appearing eyes. -- Wikipedia; Abetalipoproteinemia is a rare inherited disorder of fat metabolism that results in poor absorption of dietary fat and vitamin E. The vitamin E deficiency associated with this disease causes problems such as poor transmission of nerve impulses, muscle weakness, and degeneration of the retina that can cause blindness. Individuals with abetalipoproteinemia may be prescribed special vitamin E supplements by a physician to treat this disorder. -- Wikipedia; Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha tocopherol. It increases naturally to about 150% of normal in the maternal circulation during human pregnancies. 1 IU of vitamin E is defined as the biological equivalent of 0.667 milligrams of d-alpha-tocopherol, or of 1 milligram of dl-alpha-tocopherol acetate. The other isomers are slowly being recognized as research begins to elucidate their additional roles in the human body. Many naturopathic and orthomolecular medicine advocates suggest that vitamin E supplements contain at least 20% by weight of the other natural vitamin E isomers. Commercially available blends of natural vitamin E include "mixed tocopherols" and "high gamma tocopherol" formulas. Also selenium, Coenzyme Q10, and ample vitamin C have been shown to be essential cofactors of natural tocopherols. -- Wikipedia; Alzheimer's disease is a wasting disease of the brain. An observational trial conducted by The Johns Hopkins University Bloomberg School of Public Health found that when vitamin E is taken daily in large doses (400-1000IU) in combination with vitamin C (500-1000mg) the onset of Alzheimer's was reduced between 64 and 78%. External Link - Johns Hopkins press release -- Wikipedia; Alzheimer's disease is a wasting disease of the brain. As oxidative stress may be involved in the pathogenesis of Alzheimer's, tocopherols have been tested as both a means of prevention and treatment. The results of these studies have been mixed, with some research suggesting that high levels of vitamin E in the diet may reduce the risk of Alzheimer's, while other studies found no such link. Studies on progression have also been contradictory, with the Alzheimer?s Disease Cooperative Study suggesting that vitamin E supplementation might be beneficial, but a later trial finding no clinical benefit. Due to this contradictory and confusing evidence, vitamin E or tocopherol supplements are not currently recommended for treating or preventing Alzheimer's disease.; During feeding experiments with rats Herbert McLean Evans concluded in 1922 that besides vitamins B and C, an unknown vitamin existed. Although every other nutrition was present, the rats were not fertile. This condition could be changed by additional feeding with wheat germ. It took several years until 1936 when the substance was isolated from wheat germ and the formula C29H50O2 was determined. Evans also found that the compound reacted like an alcohol and concluded that one of the oxygen atoms was part of an OH (hydroxyl) group. As noted in the introduction, the vitamin was given its name by Evans from Greek words meaning "to bear young" with the addition of the -ol as an alcohol. The structure was determined shortly thereafter in 1938.; Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. All isomers have a chromanol ring, with a hydroxyl group which can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes. There is an alpha, beta, gamma and delta form of both the tocopherols and tocotrienols, determined by the number of methyl groups on the chromanol ring. Each form has its own biological activity, the measure of potency or functional use in the body. -- Wikipedia; Recent studies also show that vitamin E acts as an effective free radical scavenger and can lower the incidence of lung cancer in smokers. The effects are opposite to that of the clinical trials based on administering carotenoid to male smokers, that resulted in increased risk of lung cancer. Hence vitamin E is an effective antagonist to the oxidative stress that is imposed by high carotenoids in certain patients. -- Wikipedia; Synthetic vitamin E, usually marked as d,l-tocopherol or d,l tocopheryl acetate, with 50% d-alpha tocopherol moiety and 50% l-alpha-tocopherol moiety, as synthesized by an earlier process is now actually manufactured as all-racemic alpha tocopherol, with only about one alpha tocopherol molecule in 8 molecules as actual d-alpha tocpherol. The synthetic form is not as active as the natural alpha tocopherol form. The 1950's thalidomide disaster with numerous severe birth defects is a common example of d- vs l- epimer forms type problem with synthesized racemic mixtures. Information on any side effects of the synthetic vitamin E epimers is not readily available. Naturopathic and orthomolecular medicine advocates have long considered the synthetic vitamin E forms to be with little or no merit for cancer, circulatory and heart diseases. -- Wikipedia; There are three stereocenters in alpha-tocopherol, so this is a chiral molecule. The eight stereoisomers of alpha-tocopherol differ in the arrangement of groups around these stereocenters. In the image of RRR-alpha-tocopherol below, all three stereocenters are in the R form. However, if the middle of the three stereocenters were changed (so the hydrogen was now pointing down and the methyl group pointing up), this would become the structure of RSR-alpha-tocopherol. RSR-alpha-tocopherol and RRR-alpha-tocopherol are mirror-images of each other. These stereoisomers can also be named in an alternative older nomenclature, where the stereocenters are either in the d or l form.; Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. -- Wikipedia; Tocopherols (or TCP) are a class of chemical compounds of which many have vitamin E activity. It is a series of organic compounds consisting of various methylated phenols. Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rats, it was given the name "tocopherol" from the Greek words ??????? [birth], and ????????, [to bear or carry] meaning in sum "to carry a pregnancy," with the ending "-ol" signifying its status as a chemical alcohol.
cas_number 119-13-1
Properties
created_at 2010-04-08 22:05:22
updated_at 2011-07-12 21:19:07
moldb_smiles CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=CC(C)=C2O1
moldb_formula C27H46O2
moldb_average_mass 402.6529
moldb_inchi InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3
moldb_mono_mass 402.349780716
moldb_inchikey InChIKey=GZIFEOYASATJEH-UHFFFAOYSA-N
moldb_iupac 2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol
Structure Thumb
Synonyms
Synonym Source
(+)-delta-tocopherol biospider
Delta-tocopherol biospider
Vitamine e biospider
3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol, 9CI db_source
8-Methyltocol db_source
E309 db_source