.DELTA.-TOCOPHEROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H46O2
Molecular Weight	402.6529
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=CC(O)=C2

InChI

InChIKey=GZIFEOYASATJEH-VHFRWLAGSA-N

InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21372040 | https://www.ncbi.nlm.nih.gov/pubmed/27008503

δ-Tocopherol (δ-T) is a chiral organic molecule belonging to the group of tocopherol, that vary in their degree of methylation of the phenol moiety of the chromanol ring. It was revealed, that δ-Tocopherol had a more potent anticancer activity in solid tumors compared to the other tocopherols, δ-T possessed antileukemic activity of in acute myeloid leukemia (AML). δ-T induced tumor cell death through peroxisome proliferator-activated receptor γ (PPAR-γ) induction, cyclin-D1 inhibition, and modulation of redox balance. In addition, on animal models was found, that δ-tocopherol was more active than α- or γ-tocopherol in inhibiting lung tumor growth, possibly through trapping reactive oxygen and nitrogen species and inducing apoptosis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
reactive oxygen 1 Target ID: reactive oxygen Sources: https://www.ncbi.nlm.nih.gov/pubmed/21372040	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lung cancer 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21372040	Primary		Preclinical	Unknown Approved Use Unknown
Acute myeloid leukemia 136 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27008503	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
δ-tocopherol is more active than α - or γ -tocopherol in inhibiting lung tumorigenesis in vivo.	2011 Mar	21372040
Dietary, supplement, and adipose tissue tocopherol levels in relation to prostate cancer aggressiveness among African and European Americans: The North Carolina-Louisiana Prostate Cancer Project (PCaP).	2015 Sep	26053590
Reduction in Cell Viability and in Homeobox Protein Levels Following in Vitro Exposure to δ-tocopherol in Acute Myeloid Leukemia.	2016	27008503

Patents

Sample Use Guides

In Vivo Use Guide

xenograft model mice: diets supplemented with δ-tocopherol at 0.17% and 0.3%) for 49 days

Route of Administration: Oral

In Vitro Use Guide

Effects of δ-T (δ-Tocopherol) on Acute Myeloid Leukemia (AML) cells. Jurkat, TOM-1, K-562, KG-1, THP-1, and UMCL01-101 cell lines were incubated with increasing concentrations of δ-T (0-200 µM) for 72 hours. Cell viability was quantified using a tetrazolium dye reduction assay. Apoptotic induction and cell cycle arrest explained the efficacy of δ-T against KG-1 cells. The mechanism of cell growth inhibition of δ-T was through downregulation of cyclin-D1 and a set of homeobox proteins (HOXA9, PBX1, and Cdx2) that have a well-documented role in the pathobiology of AML.

Name

Type

Language

.DELTA.-TOCOPHEROL

Common Name

English

DELTA-TOCOPHEROL (CONSTITUENT OF LYCOPENE AND TOMATO EXTRACT CONTAINING LYCOPENE) [DSC]

Common Name

English

DELTA-TOCOPHEROL, D-

Common Name

English

RRR-.DELTA.-TOCOPHEROL

Common Name

English

DELTA-TOCOPHEROL

Common Name

English

8-METHYLTOCOL

Common Name

English

RRR-.ALPHA.-TOCOPHEROL IMPURITY A [EP IMPURITY]

Common Name

English

.DELTA.-TOCOPHEROL [MI]

Common Name

English

J5.309K

Code

English

Delta-tocopherol [WHO-DD]

Common Name

English

(2R)-3,4-DIHYDRO-2,8-DIMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-OL

Systematic Name

English

Classification Tree Code System Code

DSLD

3108 (Number of products:50)