Actions

alpha-Tocopherol

::concepts

Correct::journal    Racemic::vitamin    Mixture::acetate    Chembox::three    Author::title    Section::vitamin

α-Tocopherol<ref>Merck Index, 11th Edition, 9931.</ref>
colspan=2 style="background:#f8eaba; text-align:center;" Names
colspan=2 style="background:#f8eaba; text-align:center;" Identifiers{{#invoke:TemplatePar check template=Template:Chembox Identifiers opt=

3DMet= ATCCode= ATCCode_prefix= ATCCode_suffix= ATC_Supplemental= ATCvet= Abbreviations= Beilstein= CASNo1= CASNo1_Comment= CASNo1_Ref= CASNo2= CASNo2_Comment= CASNo2_Ref= CASNo3= CASNo3_Comment= CASNo3_Ref= CASNo4= CASNo4_Comment= CASNo4_Ref= CASNo5= CASNo5_Comment= CASNo5_Ref= CASNo= CASNoOther= CASNo_Comment= CASNo_Ref= ChEBI1= ChEBI1_Comment= ChEBI1_Ref= ChEBI2= ChEBI2_Comment= ChEBI2_Ref= ChEBI3= ChEBI3_Comment= ChEBI3_Ref= ChEBI4= ChEBI4_Comment= ChEBI4_Ref= ChEBI5= ChEBI5_Comment= ChEBI5_Ref= ChEBI= ChEBIOther= ChEBI_Comment= ChEBI_Ref= ChEMBL1= ChEMBL1_Comment= ChEMBL1_Ref= ChEMBL2= ChEMBL2_Comment= ChEMBL2_Ref= ChEMBL3= ChEMBL3_Comment= ChEMBL3_Ref= ChEMBL4= ChEMBL4_Comment= ChEMBL4_Ref= ChEMBL5= ChEMBL5_Comment= ChEMBL5_Ref= ChEMBL= ChEMBLOther= ChEMBL_Comment= ChEMBL_Ref= ChemSpiderID1= ChemSpiderID1_Comment= ChemSpiderID1_Ref= ChemSpiderID2= ChemSpiderID2_Comment= ChemSpiderID2_Ref= ChemSpiderID3= ChemSpiderID3_Comment= ChemSpiderID3_Ref= ChemSpiderID4= ChemSpiderID4_Comment= ChemSpiderID4_Ref= ChemSpiderID5= ChemSpiderID5_Comment= ChemSpiderID5_Ref= ChemSpiderID= ChemSpiderIDOther= ChemSpiderID_Comment= ChemSpiderID_Ref= DrugBank1= DrugBank1_Comment= DrugBank1_Ref= DrugBank2= DrugBank2_Comment= DrugBank2_Ref= DrugBank3= DrugBank3_Comment= DrugBank3_Ref= DrugBank4= DrugBank4_Comment= DrugBank4_Ref= DrugBank5= DrugBank5_Comment= DrugBank5_Ref= DrugBank= DrugBankOther= DrugBank_Comment= DrugBank_Ref= EC number= EC number_Comment= EC_number= EC_number_Comment= EINECS= Gmelin= IUPHAR_ligand= IUPHAR_ligand1= IUPHAR_ligand2= IUPHAR_ligand3= IUPHAR_ligand4= IUPHAR_ligand5= IUPHAR_ligand_Comment= IUPHAR_ligand1_Comment= IUPHAR_ligand2_Comment= IUPHAR_ligand3_Comment= IUPHAR_ligand4_Comment= IUPHAR_ligand5_Comment= IUPHAR_ligand_Other= InChI1= InChI1_Comment= InChI1_Ref= InChI2= InChI2_Comment= InChI2_Ref= InChI3= InChI3_Comment= InChI3_Ref= InChI4= InChI4_Comment= InChI4_Ref= InChI5= InChI5_Comment= InChI5_Ref= InChI= InChIKey1= InChIKey1_Ref= InChIKey2= InChIKey2_Ref= InChIKey3= InChIKey3_Ref= InChIKey4= InChIKey4_Ref= InChIKey5= InChIKey5_Ref= InChIKey= InChIKey_Ref= InChIOther= InChI_Comment= InChI_Ref= JmolOther= KEGG1= KEGG1_Comment= KEGG1_Ref= KEGG2= KEGG2_Comment= KEGG2_Ref= KEGG3= KEGG3_Comment= KEGG3_Ref= KEGG4= KEGG4_Comment= KEGG4_Ref= KEGG5= KEGG5_Comment= KEGG5_Ref= KEGG= KEGGOther= KEGG_Comment= KEGG_Ref= MeSHName= PubChem1= PubChem1_Comment= PubChem2= PubChem2_Comment= PubChem3= PubChem3_Comment= PubChem4= PubChem4_Comment= PubChem5= PubChem5_Comment= PubChem= PubChemOther= PubChem_Comment= RTECS= SMILES1= SMILES1_Comment= SMILES2= SMILES2_Comment= SMILES3= SMILES3_Comment= SMILES4= SMILES4_Comment= SMILES5= SMILES5_Comment= SMILESOther= SMILES= SMILES_Comment= StdInChI= StdInChIKey= StdInChIKey_Ref= StdInChI_Comment= StdInChI_Ref= UNII= UNII1= UNII1_Comment= UNII1_Ref= UNII2= UNII2_Comment= UNII2_Ref= UNII3= UNII3_Comment= UNII3_Ref= UNII4= UNII4_Comment= UNII4_Ref= UNII5= UNII5_Comment= UNII5_Ref= UNIIOther= UNII_Comment= UNII_Ref= UNNumber=

cat=Chemical articles with unknown parameter in Chembox preview=
@@@
This error is harmless. The message shows only in Preview, it will not show after Save.
|errNS=0}}
ChEBI
ChemSpider
EC number 200-412-2
{{safesubst:#invoke:collapsible list|main}}
UNII
colspan=2 style="background:#f8eaba; text-align:center;" Hazards{{#invoke:TemplatePar check template=Template:Chembox Hazards opt=

ExternalMSDS= ExternalSDS= GHSPictograms= GHSSignalWord= Hazards_data_page= HPhrases= PPhrases= EUClass= RPhrases= SPhrases= RSPhrases= MainHazards= IngestionHazard= InhalationHazard= EyeHazard= SkinHazard= NFPA-F= NFPA-H= NFPA-R= NFPA-S= NFPA_ref= FlashPt= FlashPtC= FlashPtF= FlashPtK= FlashPt_notes= FlashPt_ref= AutoignitionPt= AutoignitionPtC= AutoignitionPtF= AutoignitionPtK= AutoignitionPt_ref= AutoignitionPt_notes= ExploLimits= TLV= TLV-TWA= TLV-STEL= TLV-C= LD50= LDLo= LC50= LCLo= PEL= REL= IDLH= NIOSH_id= NIOSH_ref= NFPA-O

cat=Chemical articles with unknown parameter in Chembox preview=
@@@
This error is harmless. The message shows only in Preview, it will not show after Save.
|errNS=0}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what is: YesY/N?)
Infobox references
{{#invoke:TemplatePar

|check |template=Template:Chembox |all= |opt= IUPACNames= IUPACName= ImageAlt1= ImageAlt2= ImageAlt3= ImageAlt4= ImageAltL1= ImageAltL2= ImageAltL3= ImageAltL4= ImageAltR1= ImageAltR2= ImageAltR3= ImageAltR4= ImageAlt= ImageCaption1= ImageCaption2= ImageCaption3= ImageCaption4= ImageCaptionL1= ImageCaptionL2= ImageCaptionL3= ImageCaptionL4= ImageCaptionR1= ImageCaptionR2= ImageCaptionR3= ImageCaptionR4= ImageCaption= ImageFile1_Ref= ImageFile1= ImageFile2_Ref= ImageFile2= ImageFile3_Ref= ImageFile3= ImageFile4_Ref= ImageFile4= ImageFileL1_Ref= ImageFileL1= ImageFileL2_Ref= ImageFileL2= ImageFileL3_Ref= ImageFileL3= ImageFileL4_Ref= ImageFileL4= ImageFileR1_Ref= ImageFileR1= ImageFileR2_Ref= ImageFileR2= ImageFileR3_Ref= ImageFileR3= ImageFileR4_Ref= ImageFileR4= ImageFile_Ref= ImageFile= ImageName1= ImageName2= ImageName3= ImageName4= ImageNameL1= ImageNameL2= ImageNameL3= ImageNameL4= ImageNameR1= ImageNameR2= ImageNameR3= ImageNameR4= ImageName= ImageSize1= ImageSize2= ImageSize3= ImageSize4= ImageSizeL1= ImageSizeL2= ImageSizeL3= ImageSizeL4= ImageSizeR1= ImageSizeR2= ImageSizeR3= ImageSizeR4= ImageSize= Name= OtherNames= PIN= Reference= Section1= Section2= Section3= Section4= Section5= Section6= Section7= Section8= Section9= SystematicName= Verifiedfields= Watchedfields= verifiedrevid= Verifiedimages= general_note= show_infobox_ref= show_ss_note= style-left-column-width= style= width |cat=Chemical articles with unknown parameter in Chembox

|format=0|preview=
@@@
This error is harmless. The message shows only in Preview, it will not show after Save.
|errNS=0}}

α-Tocopherol is a type of tocopherol or vitamin E. It has E number "E307".

α-Tocopherol is a form of vitamin E that is preferentially absorbed and accumulated in humans.<ref>{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref> 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.

There are three stereocenters in alpha-tocopherol, so this is a chiral molecule.<ref>{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref> The eight stereoisomers of alpha-tocopherol differ in the arrangement of groups around these stereocenters. In the image of RRR-alpha-tocopherol, 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 diastereomers 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.<ref>{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref>

1 IU of tocopherol is defined as ⅔ 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) α-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 α-tocopherol".<ref>Composition of Foods Raw, Processed, Prepared USDA National Nutrient Database for Standard Reference, Release 20 USDA, February 2008</ref>


Alpha-Tocopherol sections
Intro  References  

PREVIOUS: IntroNEXT: References
<<>>