alpha-Tocopherol (Compound)

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ID	237
Name	alpha-Tocopherol
Synonyms	Vitamin E; (+)-alpha-Tocopherol; D-alpha-Tocopherol
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000237 (alpha-Tocopherol) 3D Structure for EE000237 (alpha-Tocopherol) 14985 -OEChem-02282312453D 81 82 0 1 0 0 0 0 0999 V2000 0.7439 -1.3977 -0.1232 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3183 1.4276 -1.3890 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7693 -2.3982 0.9123 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6874 -2.5672 1.3684 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6165 -1.9523 2.1151 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6525 -2.5615 0.1814 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1405 -2.6928 -0.4929 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0989 -2.7639 0.6462 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0429 -1.6226 1.6984 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1332 -1.3155 -1.1902 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2487 -3.7271 0.3089 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0372 -0.7796 0.4579 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4179 -0.1428 -0.2451 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9105 -0.7238 -0.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4293 1.2220 -0.9482 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6441 2.4603 -0.0469 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8732 -3.8345 -1.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6255 2.5062 1.1114 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1850 -0.0589 0.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9230 0.0704 -1.5212 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1483 2.5701 0.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0658 0.7930 -1.8615 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5670 3.7209 -0.9179 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1977 0.7256 -1.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1393 2.5588 1.8561 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3455 2.5408 1.4458 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4159 -0.1114 0.9522 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7053 0.1538 -2.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0817 1.6448 -3.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2834 2.4710 2.6512 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6667 3.7844 0.6131 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8061 -3.4779 1.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9685 -1.7257 2.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6224 -2.7160 2.9017 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1755 -1.0446 2.5506 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3833 -3.3490 -0.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5813 -1.6035 -0.3401 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1319 -2.8536 -0.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3472 -2.0402 1.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1764 -3.7475 1.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6077 -2.5429 1.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5216 -1.0968 2.5322 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9064 -1.3241 -1.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1865 -1.1488 -1.7167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2003 -4.5402 1.0408 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6638 -4.0136 -0.5705 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2816 -3.6587 -0.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6454 -0.1245 0.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3791 -0.2983 0.2588 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4951 1.3333 -1.5134 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2274 1.2066 -1.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6488 2.4037 0.3905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9586 -3.6754 -2.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6984 -3.9064 -2.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7988 -4.7981 -0.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8456 3.3902 1.7250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7818 1.6500 1.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9107 1.7245 0.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9978 3.4798 0.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3771 3.7245 -1.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6722 4.6223 -0.3052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6221 3.7871 -1.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3301 3.4275 2.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3357 1.6725 2.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5235 1.6547 0.8268 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6503 -1.1416 1.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3076 0.2617 0.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2736 0.4922 1.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4229 1.1985 -2.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1785 -0.3167 -1.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8863 -0.3435 -3.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9701 2.6994 -2.8179 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0179 1.5140 -3.6457 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2994 1.4000 -3.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1648 3.3469 3.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3292 2.4224 2.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0758 1.5776 3.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3942 4.7036 1.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1454 3.7706 -0.3488 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7384 3.8311 0.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1056 2.1425 -2.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 14 1 0 0 0 0 2 24 1 0 0 0 0 2 81 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 3 11 1 0 0 0 0 4 6 1 0 0 0 0 4 32 1 0 0 0 0 4 33 1 0 0 0 0 5 9 1 0 0 0 0 5 34 1 0 0 0 0 5 35 1 0 0 0 0 6 8 1 0 0 0 0 6 36 1 0 0 0 0 6 37 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 0 0 0 0 7 38 1 0 0 0 0 8 39 1 0 0 0 0 8 40 1 0 0 0 0 9 12 1 0 0 0 0 9 41 1 0 0 0 0 9 42 1 0 0 0 0 10 13 1 0 0 0 0 10 43 1 0 0 0 0 10 44 1 0 0 0 0 11 45 1 0 0 0 0 11 46 1 0 0 0 0 11 47 1 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 13 15 1 0 0 0 0 13 48 1 0 0 0 0 13 49 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 15 50 1 0 0 0 0 15 51 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 16 52 1 0 0 0 0 17 53 1 0 0 0 0 17 54 1 0 0 0 0 17 55 1 0 0 0 0 18 21 1 0 0 0 0 18 56 1 0 0 0 0 18 57 1 0 0 0 0 19 24 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 58 1 0 0 0 0 21 59 1 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 23 60 1 0 0 0 0 23 61 1 0 0 0 0 23 62 1 0 0 0 0 25 26 1 0 0 0 0 25 63 1 0 0 0 0 25 64 1 0 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 26 65 1 0 0 0 0 27 66 1 0 0 0 0 27 67 1 0 0 0 0 27 68 1 0 0 0 0 28 69 1 0 0 0 0 28 70 1 0 0 0 0 28 71 1 0 0 0 0 29 72 1 0 0 0 0 29 73 1 0 0 0 0 29 74 1 0 0 0 0 30 75 1 0 0 0 0 30 76 1 0 0 0 0 30 77 1 0 0 0 0 31 78 1 0 0 0 0 31 79 1 0 0 0 0 31 80 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 14985 > <PUBCHEM_CONFORMER_RMSD> 1.6 > <PUBCHEM_CONFORMER_DIVERSEORDER> 6 68 33 52 75 7 1 60 26 5 4 72 78 25 36 18 49 8 63 47 20 2 43 76 24 35 67 32 14 9 61 56 37 73 57 53 15 31 71 27 59 55 13 28 3 41 77 22 23 11 66 69 34 50 12 39 46 54 19 64 38 30 10 65 62 40 45 70 44 74 21 42 17 16 58 29 51 48 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 14 1 -0.36 12 -0.14 14 0.08 19 -0.14 2 -0.53 20 -0.14 22 -0.14 24 0.08 27 0.14 28 0.14 29 0.14 3 0.28 81 0.45 9 0.14 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 12.8 > <PUBCHEM_PHARMACOPHORE_FEATURES> 7 1 1 acceptor 1 17 hydrophobe 1 2 donor 1 23 hydrophobe 3 26 30 31 hydrophobe 6 1 3 5 9 12 14 rings 6 12 14 19 20 22 24 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 31 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 3 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 9 > <PUBCHEM_CONFORMER_ID> 00003A8900000006 > <PUBCHEM_MMFF94_ENERGY> 75.1299 > <PUBCHEM_FEATURE_SELFOVERLAP> 35.549 > <PUBCHEM_SHAPE_FINGERPRINT> 10673678 19 17758674448447900813 10815517 723 17975687286866316242 12156800 1 18337654417311407328 12788726 201 18337678624047910191 131258 38 18120627216427356642 13617811 41 18187918475062387509 14931854 50 18340198610282962461 14932702 115 18272643511644135289 15297060 5 18129381505672795299 15420108 30 17327454727822297138 161222 10 17984728652285261813 17138139 8 18337954605233460812 17818456 19 18268421330874349266 19319366 153 18188211988510142747 20511986 3 18114455674249732893 20715895 44 17468186744490211621 20764821 26 18338234989605269065 21033650 10 18265639699863579286 21860390 5 17553195910712719282 24941158 1 15213842849100826553 3052486 1 18410847772369006144 3493558 16 18125157135203041458 4066623 53 18053087700240172981 463206 1 18337954476474652217 469060 322 17898886618998833489 5171179 24 17985822863859714769 > <PUBCHEM_SHAPE_MULTIPOLES> 626.23 10.47 5.41 2.44 2.17 0.27 -0.6 -2.3 -3.57 6.14 1.31 -2.05 -1.05 -2.09 > <PUBCHEM_SHAPE_SELFOVERLAP> 1256.404 > <PUBCHEM_SHAPE_VOLUME> 371.9 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	The most important compound with vitamin E activity.
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin E compounds > Tocopherols
CAS number	59-02-9
PubChem ID	14985
ChEBI ID	18145
FooDB ID	FDB000565
HMDB ID	HMDB0001893

Chemical data

MolDBi data

IUPAC Name	(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional IUPAC Name	VitaE
Formula	C29H50O2
InChI	InChI=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
InChI Key	GVJHHUAWPYXKBD-IEOSBIPESA-N
Molecular weight	430.7061
Exact mass	430.381080844
SMILES	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Prenol lipids
Sub Class	Quinone and hydroquinone lipids
Direct Parent	Tocopherols
Alternative Parents	Diterpenoids 1-benzopyrans Alkyl aryl ethers Benzenoids Oxacyclic compounds Hydrocarbon derivatives

Publications with alpha-Tocopherol

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of alpha-Tocopherol in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of alpha-Tocopherol with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of alpha-Tocopherol with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of alpha-Tocopherol exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of alpha-Tocopherol exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication