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T1782

Sigma-Aldrich

(+)-γ-Tocopherol

≥96% (HPLC)

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Synonym(s):
gamma-Tocopherol, (R,R,R)-γ-Tocopherol, 7,8-Dimethyltocol
Empirical Formula (Hill Notation):
C28H48O2
CAS Number:
54-28-4
Molecular Weight:
416.68
Beilstein:
93072
EC Number:
200-201-5
MDL number:
MFCD00066529
UNSPSC Code:
12352211
eCl@ss:
34058016
PubChem Substance ID:
24899992
NACRES:
NA.79

Quality Level

200

Assay

≥96% (HPLC)

form

liquid

technique(s)

HPLC: suitable

color

dark brown
 colorless to dark yellow

storage temp.

2-8°C

SMILES string

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2cc(O)c(C)c(C)c2O1

InChI

1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1

InChI key

QUEDXNHFTDJVIY-DQCZWYHMSA-N

Gene Information

human ... HMGCR(3156)

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Application

(+)-γ-Tocopherol has been used:
  • as reference material for the quantification of γ-tocopherol in the oil sample using high performance liquid chromatography with diode array detector (HPLC/DAD)(192}
  • as a component of diet to feed vitamin-E-depleted rats to study its effects
  • as an additive in the feed to study its effects in reducing dietary induced oxidative stress in vivo and improving meat lipid stability in broilers

Biochem/physiol Actions

Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble antioxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. Various isofroms and analogues of tocopherol have opposing and differentiated regulatory activities in vivo.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Graded dietary levels of RRR-gamma-tocopherol induce a marked increase in the concentrations of alpha-and gamma-tocopherol in nervous tissues, heart, liver and muscle of vitamin-E-deficient rats
Clement M, et al.
Biochimica et biophysica acta. General subjects, 1334(2-3), 173-118 (1997)
Characterization of oil extracted from the kernel of the fruit of cumare?s palm (Astrocaryum chambira Barret)
Ramirez-Nino MA, et al.
Revista da Faculdade de Odontologia de Aracatuba, 71(1), 8415-8422 (2018)
Chandra K Singh et al.
Oncotarget, 5(11), 3651-3661 (2014-07-09)
Studies have shown that vitamin E and selenium possess antiproliferative effects against prostate cancer (PCa). However, results from the Selenium and Vitamin E Cancer Prevention Trial (SELECT) suggest that vitamin E (α-tocopheryl acetate; 400 mg) and/or selenium (L-selenomethionine; 200 μg)
The potency of alpha-and gamma-tocopherol, and their combination, in reducing dietary induced oxidative stress in vivo and improving meat lipid stability in broilers
Tomavzin U, et al.
Archiv fur Geflugelkunde, 77, 266-274 (2013)
Rebecca Gmoser et al.
Bioengineered, 11(1), 582-598 (2020-05-26)
By-products from the food sector with a high load of organic matter present both a waste-handling problem related to expenses and to the environment, yet also an opportunity. This study aims to increase the value of stale bread and brewers
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Protocols

HPLC Analysis of Fat Soluble Vitamins by Normal Phase Chromatography on Ascentis® Si

Separation of (±)-α-Tocopherol, analytical standard; Menadione (K3), analytical standard; (+)-γ-Tocopherol, analytical standard; Cholecalciferol (D3), analytical standard

HPLC Analysis of Vitamins, Fat Soluble (A and E), on SUPELCOSIL™ LC-18

Separation of δ-Tocopherol, analytical standard; Retinyl acetate; (+)-γ-Tocopherol; α-Tocopherol, ≥95.5%; Retinol; Vitamin A (acetate), meets USP testing specifications.

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