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Revision as of 05:36, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,294 edits Saving copy of the {{chembox}} taken from revid 470088758 of page Alpha-Tocopherol for the Chem/Drugbox validation project (updated: '').  Latest revision as of 02:06, 12 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,951 edits dark mode fix 
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{{lowercase title}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{Chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443660118 | verifiedrevid = 477319727
|Name = α-Tocopherol | Name = α-Tocopherol
|Reference = <ref>''Merck Index'', 11th Edition, '''9931'''.</ref> | Reference = <ref>''Merck Index'', 11th Edition, '''9931'''.</ref>
|ImageFile=Tocopherol, alpha-.svg | ImageFile = Tocopherol, alpha-.svg
| ImageClass = skin-invert-image
|ImageSize=200px | ImageSize = 300px
|Name=&alpha;-Tocopherol
| ImageFile1 = Vitamin-E-from-xtal-3D-bs-17.png
⚫ |IUPACName=(2''R)-2,5,7,8-Tetramethyl-2--6-chromanol
| ImageClass1 = bg-transparent
⚫ |OtherNames=
| ImageSize1 = 300px
| ImageFile2 = Sample of alpha-tocopherol.jpg
| ImageSize2 = 300px
⚫ | PIN = (2''R'')-2,5,7,8-Tetramethyl-2--3,4-dihydro-2''H''-1-benzopyran-6-ol
⚫ | OtherNames =
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14265 | ChemSpiderID = 14265
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
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| UNII = N9PR3490H9 | UNII = N9PR3490H9
| InChIKey = GVJHHUAWPYXKBD-IEOSBIPEBS | InChIKey = GVJHHUAWPYXKBD-IEOSBIPEBS
| SMILES1 = Cc1c(c2c(c(c1O)C)CC(O2)(C)CCC(C)CCC(C)CCCC(C)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1 | StdInChI = 1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
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| StdInChIKey = GVJHHUAWPYXKBD-IEOSBIPESA-N | StdInChIKey = GVJHHUAWPYXKBD-IEOSBIPESA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=59-02-9 | CASNo = 59-02-9
| PubChem = 14985 | PubChem = 14985
| EINECS = 200-412-2 | EINECS = 200-412-2
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00163 | DrugBank = DB00163
| SMILES = Oc2c(c(c1O(CCc1c2C)(C)CCC(C)CCC(C)CCCC(C)C)C)C | SMILES = Cc1c(O)c(C)c(CC(CCC(CCC(CCCC(C)C)C)C)(C)O2)c2c1C
| InChI = 1/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1 | InChI = 1/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
⚫ }}
|Section2={{Chembox Properties
⚫ | Formula = C<sub>29</sub>H<sub>50</sub>O<sub>2</sub>
⚫ | MolarMass = 430.71 g/mol
| Appearance = yellow-brown viscous liquid
⚫ | Density = 0.950 g/cm<sup>3</sup>
| MeltingPtC = 2.5 to 3.5
| BoilingPtC = 200 to 220
| BoilingPt_notes = at 0.1 mmHg
⚫ | Solubility = insoluble
| SolubleOther = soluble in alcohol, ], ], oils
⚫ }}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = A11 | ATCCode_prefix = A11
| ATCCode_suffix = HA03 | ATCCode_suffix = HA03
}} }}
|Section2={{Chembox Properties |Section7={{Chembox Hazards
| NFPA-H = 1
⚫ | Formula=C<sub>29</sub>H<sub>50</sub>O<sub>2</sub>
| NFPA-F = 1
⚫ | MolarMass=430.71 g/mol
| NFPA-R = 0
| Appearance=
| MainHazards =
⚫ | Density=0.950 g/cm³
| FlashPt =
| MeltingPt=2.5–3.5&nbsp;°C
| AutoignitionPt =
| BoilingPt=200–220&nbsp;°C at 0.1 mmHg
}}
⚫ | Solubility=
⚫ }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
⚫ }}
}} }}

'''α-Tocopherol''' (''alpha''-tocopherol) is a type of ]. Its ] is "E307". Vitamin E exists in eight different forms, four ]s and four ]s. All feature a ] ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain, along with an aromatic ring is situated near the carbonyls in the fatty acyl chains of the phospholipid bilayer, allows for penetration into biological membranes.<ref>{{cite journal |last1=Burton |first1=G. W. |last2=Ingold |first2=K. U. |title=Vitamin E: application of the principles of physical organic chemistry to the exploration of its structure and function |journal=Accounts of Chemical Research |date=1 June 1986 |volume=19 |issue=7 |pages=194–201 |doi=10.1021/ar00127a001}}</ref> It is found most in the membrane's non-raft domains, associated with omega-3 and 6 fatty acids, to partially prevent oxidation.<ref>{{cite journal |last1=Atkinson |first1=Jeffrey |last2=Harroun |first2=Thad |last3=Wassall |first3=Stephen R. |last4=Stillwell |first4=William |last5=Katsaras |first5=John |title=The location and behavior of α‐tocopherol in membranes |journal=Molecular Nutrition & Food Research |date=May 2010 |volume=54 |issue=5 |pages=641–651 |doi=10.1002/mnfr.200900439}}</ref> The most prevalent form, α-tocopherol, is involved in molecular, cellular, biochemical processes closely related to overall ] and ] ]. Compared to the others, α-tocopherol is preferentially absorbed and accumulated in humans.

] is found in a variety of tissues, being lipid-soluble, and taken up by the body in a wide variety of ways. Ongoing research is believed to be "critical for manipulation of vitamin E homeostasis in a variety of oxidative stress-related disease conditions in humans."<ref>{{cite journal | vauthors = Rigotti A | title = Absorption, transport, and tissue delivery of vitamin E | journal = Molecular Aspects of Medicine | volume = 28 | issue = 5–6 | pages = 423–36 | year = 2007 | pmid = 17320165 | doi = 10.1016/j.mam.2007.01.002 }}</ref> One of these disease conditions is the α-tocopherol role in the use by ] parasites to protect themselves from the highly oxidative environment in ].<ref>{{cite journal | vauthors = Shichiri M, Ishida N, Hagihara Y, Yoshida Y, Kume A, Suzuki H | title = Probucol induces the generation of lipid peroxidation products in erythrocytes and plasma of male cynomolgus macaques | journal = Journal of Clinical Biochemistry and Nutrition | volume = 64 | issue = 2 | pages = 129–142| year = 2019 | pmid = 30936625 |pmc = 6436040 | doi = 10.3164/jcbn.18-7}}</ref> A second of these disease conditions is the α-tocopherol antioxidant properties' role cardiovascular heart disease. In preventing LDL (low-density ]) oxidation, it is able to decrease chances of atherosclerosis and arterial build-up.<ref>{{cite journal |last1=Singh |first1=U. |last2=Devaraj |first2=S. |last3=Jialal |first3=I. |title=VITAMIN E, OXIDATIVE STRESS, AND INFLAMMATION |journal=Annual Review of Nutrition |date=21 August 2005 |volume=25 |issue=1 |pages=151–174 |doi=10.1146/annurev.nutr.24.012003.132446}}</ref>

== Synthesis ==
To synthesize the ⍺-diastereomer selectively, tocol acetate is transformed to the naturally occurring, kinetically favored α-Tocopherol after being catalyzed by the lipase enzyme. This reaction occurs under biological conditions, commonly in the digestive system.<ref>{{cite journal |last1=Mizuguchi |first1=Eisaku |last2=Takemoto |first2=Masumi |last3=Achiwa |first3=Kazuo |title=An enzyme-catalyzed synthesis of natural α-tocopherol |journal=Tetrahedron: Asymmetry |date=January 1993 |volume=4 |issue=9 |pages=1961–1964 |doi=10.1016/s0957-4166(00)82239-9}}</ref>

== Stereoisomers ==
α-Tocopherol has three ]s, so it is a ] molecule.<ref>{{cite journal | vauthors = Jensen SK, Lauridsen C | title = Alpha-tocopherol stereoisomers | journal = Vitamins and Hormones | volume = 76 | pages = 281–308 | year = 2007 | pmid = 17628178 | doi = 10.1016/S0083-6729(07)76010-7 | isbn = 9780123735928 }}</ref> The eight ] of α-tocopherol differ in the configuration of these stereocenters. ''RRR''-α-tocopherol is the natural one.<ref>{{cite journal | vauthors = Brigelius-Flohé R, Traber MG | title = Vitamin E: function and metabolism | journal = FASEB Journal | volume = 13 | issue = 10 | pages = 1145–55 | date = July 1999 | pmid = 10385606 | doi = 10.1096/fasebj.13.10.1145 | s2cid = 7031925 | url = http://www.fasebj.org/cgi/pmidlookup?view=long&pmid=10385606 | doi-access = free }}</ref> The older name of ''RRR''-α-tocopherol is ''d''-α-tocopherol, but this ''d/l'' naming should no longer be used, because whether ''l''-α-tocopherol should mean ''SSS'' enantiomer or the ''SRR'' diastereomer is not clear, from historical reasons. The ''SRR'' may be named 2-''epi''-α-tocopherol, the diastereomeric mixture of ''RRR''-α-tocopherol and 2-''epi''-α-tocopherol may be called 2-''ambo''-α-tocopherol (formerly named ''dl''-α-tocopherol). The mixture of all eight diastereomers is called ''all''-''rac''-α-tocopherol.<ref name="IUPAC1">, from https://www.degruyter.com/document/doi/10.1351/pac198254081507/pdf</ref> The α-Tocopherol is the most active diastereomer biologically, while being maintained at a high level in plasma and tissues of many different animal species.<ref>{{cite journal |last1=Jensen |first1=Søren K. |last2=Nørgaard |first2=Jan V. |last3=Lauridsen |first3=Charlotte |title=Bioavailability of α-tocopherol stereoisomers in rats depends on dietary doses of all-rac - or RRR-α-tocopheryl acetate |journal=British Journal of Nutrition |date=March 2006 |volume=95 |issue=3 |pages=477–487 |doi=10.1079/bjn20051667 |url=https://www.cambridge.org/core/journals/british-journal-of-nutrition/article/bioavailability-of-tocopherol-stereoisomers-in-rats-depends-on-dietary-doses-of-allrac-or-rrrtocopheryl-acetate/921CFDBA1B7B2923CD5937F2069BE1BA |access-date=31 October 2024}}</ref>

One IU of tocopherol is defined as {{frac|2|3}} milligram of ''RRR''-α-tocopherol (formerly named ''d''-α-tocopherol). 1 IU is also defined as 0.9&nbsp;mg of an equal mix of the eight stereoisomers, which is a ], ]. This mix of stereoisomers is often called ''dl''-α-tocopheryl acetate.<ref>{{cite web|archive-url=https://web.archive.org/web/20120219164132/http://www.nal.usda.gov/fnic/foodcomp/Data/SR20/SR20_doc.pdf |archive-date=2012-02-19 |url=https://www.ars.usda.gov/ARSUserFiles/80400525/Data/SR20/SR20_doc.pdf |title=Composition of Foods Raw, Processed, Prepared USDA National Nutrient Database for Standard Reference, Release 20 |publisher=] |date=February 2008 |url-status=dead }}</ref> Starting with May 2016, the IU unit is made obsolete, such that 1&nbsp;mg of "Vitamin E" is 1&nbsp;mg of d-alpha-tocopherol or 2&nbsp;mg of dl-alpha-tocopherol.<ref name=NIH-Calc>{{cite web |title=Unit Conversions |url=https://dietarysupplementdatabase.usda.nih.gov/Conversions.php |publisher=] |access-date=2018-11-21}}</ref>

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== References ==
{{Reflist}}

{{Vitamin}}

{{DEFAULTSORT:Tocopherol, Alpha-}}
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