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T3634

(+)-α-Tocopherol

from vegetable oil, Type V, ~1000 IU/g

Synonym(s):

2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol, 5,7,8-Trimethyltocol, D-α-Tocopherol, Vitamin E

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About This Item

Empirical Formula (Hill Notation):
C29H50O2
CAS Number:
Molecular Weight:
430.71
NACRES:
NA.79
PubChem Substance ID:
eCl@ss:
34058016
UNSPSC Code:
12352205
EC Number:
200-412-2
MDL number:
Beilstein/REAXYS Number:
4712525
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biological source

vegetable oil

Quality Level

type

Type V

form

viscous liquid

specific activity

~1000 IU/g

color

clear yellow to red

refractive index

n20/D 1.505 (lit.)

bp

200-220 °C/0.1 mmHg (lit.)

density

0.95 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

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

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

General description

This product is miscible with chloroform or ethanol. It is practically insoluble in water but it is miscible with ether, acetone, and vegetable oils. It is unstable to alkaline conditions.
α-Tocopherol is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase. It is the major form of Vitamin E in human plasma. It is present in sunflower seed oil.

Application

(+)-α-Tocopherol has been used:
  • as a food supplement for juvenile cobia fish
  • to evaluate its protective effect on bisphenol A induced oxidative stress in rats
  • to test its chemopreventive efficacy in estrogen-mediated mammary cancer rats

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 anti-oxidants 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.
α-Tocopherol is essential for the photosynthesis in Synechocystis sp. strain PCC 6803. Supplementation with α-Tocopherol decreases lipid peroxidation and platelet aggregation. It inhibits protein kinase C and may play key role in gene regulation.

Packaging

Packaged under argon in a sealed ampule.

Analysis Note

Approx. 670 mg D-α-tocopherol per gram. The non-α content is typically between 5-35 mg/g

Other Notes

Mixed constitutional (α, β, γ, δ) isomers.

Disclaimer

Subject to air oxidation.

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1 of 1

This Item
V-020T153947783
biological source

vegetable oil

biological source

-

biological source

vegetable oil

biological source

-

form

viscous liquid

form

liquid

form

liquid (≥0.88M based on potency, density and molecular wt.)

form

liquid

storage temp.

−20°C

storage temp.

−70°C

storage temp.

2-8°C

storage temp.

-10 to -25°C

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

100

bp

200-220 °C/0.1 mmHg (lit.)

bp

-

bp

200-220 °C/0.1 mmHg (lit.)

bp

-

density

0.95 g/mL at 25 °C (lit.)

density

0.950 g/mL at 20 °C (lit.)

density

0.95 g/mL at 25 °C (lit.)

density

0.950 g/mL at 20 °C (lit.)


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Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)



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Influence of alpha-tocopherol and alpha-lipoic acid on bisphenol-A-induced oxidative damage in liver and ovarian tissue of rats
Avci B, et al.
Toxicology and Industrial Health, 32(8), 1381-1390 (2016)
Taro Sakamoto et al.
Journal of clinical biochemistry and nutrition, 66(2), 116-123 (2020-04-02)
Glutathione peroxidase 4 (GPx4) is a unique antioxidant enzyme that directly reduces the phospholipid hydroperoxides (PLOOH) generated in biomembranes using glutathione as the reductant. We have previously reported that the Caenorhabditis elegans gpx-quad mutant, which lacks all homologous genes of
Blood alpha-tocopherol, gamma-tocopherol levels and risk of prostate cancer: a meta-analysis of prospective studies
Cui R, et al.
Testing, 9(3), e93044-e93044 (2014)



Global Trade Item Number

SKUGTIN
T3634-10G04061837344763
T3634-100G04061837344756

Questions

1–4 of 4 Questions  
  1. Could you please clarify whether the entire 10g of the compound is α-Tocopherol, or does the 10g compound actually contain 6,7g (670 mg/g * 10g) of α-Tocopherol, considering the specified concentration?

    1 answer
    1. The product comprises approximately 670 mg D-α-tocopherol per gram, making the contents of the 10 gram package size approximately 6700 mg or 6.7 g D-α -Tocopherol.

      Helpful?

  2. Regarding Sigma product T3634: What are the plants used in the vegetable oil for this product?  Are any GMO? What is the country of origin of this product (Manufacture country)? Thank you.

    1 answer
    1. This material is derived from edible vegetable oils blended with soybean oil. The specific vegetable sources, other than soy, are not disclosed. This product is intended for research use only and not considered non-GMO. Historically, this material has been manufactured in the United States. As the country of origin may change, please refer to the lot specific Certificate of Orgin to confirm at the link below, under the ‘Certificate of Origin’ tab:
      https://www.sigmaaldrich.com/product/sigma/t3634Z#product-documentation

      Helpful?

  3. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  4. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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