(R,R,R)-alpha-tocopherol (CHEBI:18145)

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CHEBI:18145 - (R,R,R)-α-tocopherol

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ChEBI Name	(R,R,R)-α-tocopherol

ChEBI ID	CHEBI:18145

ChEBI ASCII Name	(R,R,R)-alpha-tocopherol

Definition	An α-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of α-tocopherol, it is found particularly in sunflower and olive oils.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:46509, CHEBI:10336, CHEBI:12343

Supplier Information	ChemicalBook:CB41119639, eMolecules:982283, ZINC000000119675

Download	Molfile XML SDF

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M END): 20 ms

reading 81 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

81 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Wikipedia	License
α-Tocopherol (alpha-tocopherol) is a type of vitamin E. Its E number is "E307". Vitamin E exists in eight different forms, four tocopherols and four tocotrienols. All feature a chromane 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. It is found most in the membrane's non-raft domains, associated with omega-3 and 6 fatty acids, to partially prevent oxidation. The most prevalent form, α-tocopherol, is involved in molecular, cellular, biochemical processes closely related to overall lipoprotein and lipid homeostasis. Compared to the others, α-tocopherol is preferentially absorbed and accumulated in humans. Vitamin E 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." One of these disease conditions is the α-tocopherol role in the use by malaria parasites to protect themselves from the highly oxidative environment in erythrocytes. A second of these disease conditions is the α-tocopherol antioxidant properties' role cardiovascular heart disease. In preventing LDL (low-density lipoprotein) oxidation, it is able to decrease chances of atherosclerosis and arterial build-up.
Read full article at Wikipedia

Formula

C29H50O2

Net Charge

Average Mass

430.70610

Monoisotopic Mass

430.38108

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

InChIKey

GVJHHUAWPYXKBD-IEOSBIPESA-N

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2c(C)c(O)c(C)c(C)c2O1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	From MetaboLights See: MetaboLights Study
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI
Homo sapiens (NCBI:txid9606)	Found in faeces (UBERON:0001988). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in saliva (UBERON:0001836). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in breast milk (ENVO:02000031). See: PubMed

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. (via tocol ) (via vitamin E ) food antioxidant An antioxidant that used as a food additives to help guard against food deterioration. (via alpha-tocopherol )

Biological Role(s):	EC 2.7.11.13 (protein kinase C) inhibitor An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13). immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. antiviral agent A substance that destroys or inhibits replication of viruses. micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via alpha-tocopherol ) algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. food antioxidant An antioxidant that used as a food additives to help guard against food deterioration. (via alpha-tocopherol ) fat-soluble vitamin (role) Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess. (via vitamin E )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. antiatherogenic agent A cardiovascular drug that prevents atherogenesis, the accumulation of lipid-containing plaques on the innermost layers of the arteries. Compare with antiatherosclerotic agent. anticoagulant An agent that prevents blood clotting. immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. food antioxidant An antioxidant that used as a food additives to help guard against food deterioration. (via alpha-tocopherol )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(R,R,R)-α-tocopherol (CHEBI:18145) has role algal metabolite (CHEBI:84735) (R,R,R)-α-tocopherol (CHEBI:18145) has role antiatherogenic agent (CHEBI:50855) (R,R,R)-α-tocopherol (CHEBI:18145) has role anticoagulant (CHEBI:50249) (R,R,R)-α-tocopherol (CHEBI:18145) has role antioxidant (CHEBI:22586) (R,R,R)-α-tocopherol (CHEBI:18145) has role antiviral agent (CHEBI:22587) (R,R,R)-α-tocopherol (CHEBI:18145) has role EC 2.7.11.13 (protein kinase C) inhibitor (CHEBI:37700) (R,R,R)-α-tocopherol (CHEBI:18145) has role immunomodulator (CHEBI:50846) (R,R,R)-α-tocopherol (CHEBI:18145) has role micronutrient (CHEBI:27027) (R,R,R)-α-tocopherol (CHEBI:18145) has role nutraceutical (CHEBI:50733) (R,R,R)-α-tocopherol (CHEBI:18145) has role plant metabolite (CHEBI:76924) (R,R,R)-α-tocopherol (CHEBI:18145) is a α-tocopherol (CHEBI:22470) (R,R,R)-α-tocopherol (CHEBI:18145) is enantiomer of (S,S,S)-α-tocopherol (CHEBI:46430)

Incoming	α-tocopheryloxyacetic acid (CHEBI:194185) has functional parent (R,R,R)-α-tocopherol (CHEBI:18145) 13-hydroxy-α-tocopherol (CHEBI:84962) has functional parent (R,R,R)-α-tocopherol (CHEBI:18145) (S,S,S)-α-tocopherol (CHEBI:46430) is enantiomer of (R,R,R)-α-tocopherol (CHEBI:18145)

IUPAC Name

(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol

Synonyms	Sources
(+)-α-tocopherol	UniProt
(+)-alpha-tocopherol	ChemIDplus
(+)-α-tocopherol	ChemIDplus
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol	IUPAC
(2R)-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]CHROMAN-6-OL	PDBeChem
(2R,4'R,8'R)-alpha-tocopherol	ChemIDplus
(2R,4'R,8'R)-α-tocopherol	ChemIDplus
(all-R)-α-tocopherol	ChemIDplus
(R,R,R)-α-tocopherol	ChemIDplus
5,7,8-trimethyltocol	ChemIDplus
alpha-Tocopherol	KEGG COMPOUND
d-α-tocopherol	ChemIDplus
RRR-α-tocopherol	ChEBI
Vitamin E	KEGG COMPOUND

Manual Xrefs	Databases
14265	ChemSpider
4280	DrugCentral
Alpha-Tocopherol	Wikipedia
ALPHA-TOCOPHEROL	MetaCyc
C00007366	KNApSAcK
C02477	KEGG COMPOUND
DB00163	DrugBank
FDB000565	FooDB
HMDB0001893	HMDB
LMPR02020001	LIPID MAPS
VIV	PDBeChem
View more database links

Registry Numbers	Types	Sources
5300493	Beilstein Registry Number	Beilstein
59-02-9	CAS Registry Number	KEGG COMPOUND
59-02-9	CAS Registry Number	NIST Chemistry WebBook
59-02-9	CAS Registry Number	ChemIDplus
94012	Reaxys Registry Number	Reaxys

Citations	Types	Sources
11427352	PubMed citation	Europe PMC
12899840	PubMed citation	Europe PMC
14657365	PubMed citation	Europe PMC
16512933	PubMed citation	Europe PMC
17031012	PubMed citation	Europe PMC
17310859	PubMed citation	Europe PMC
19389964	PubMed citation	Europe PMC
19663978	PubMed citation	Europe PMC
20209471	PubMed citation	Europe PMC
21591326	PubMed citation	Europe PMC
23599266	PubMed citation	Europe PMC
28694484	PubMed citation	Europe PMC
31013594	PubMed citation	Europe PMC
33197771	PubMed citation	Europe PMC

Last Modified

03 January 2023

CHEBI:18145 - (R,R,R)-α-tocopherol

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