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.
EC number 200-412-2
{{safesubst:#invoke:collapsible list|main}}
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.
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

|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

This error is harmless. The message shows only in Preview, it will not show after Save.

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