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Merck

62320

(±)-α-Lipoic acid

≥98.0% (HPLC), solid

Synonim(y):

(±)-1,2-Dithiolane-3-pentanoic acid, 6,8-Dithiooctanoic acid, DL-α-Lipoic acid, DL-6,8-Thioctic acid, Lip(S2)

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5 G

408,00 zł

25 G

1260,00 zł

408,00 zł

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Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):
C8H14O2S2
Numer CAS:
1077-28-7
Masa cząsteczkowa:
206.33
UNSPSC Code:
12352100
PubChem Substance ID:
57651855
NACRES:
NA.21
EC Number:
214-071-2
MDL number:
MFCD00005474
Beilstein/REAXYS Number:
81853

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Nazwa produktu

(±)-α-Lipoic acid, ≥98.0%

SMILES string

[OC(=O)CCCCC1CCSS1]
OC(=O)CCCCC1CCSS1

InChI

[1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)]
1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

InChI key

[AGBQKNBQESQNJD-UHFFFAOYSA-N]
AGBQKNBQESQNJD-UHFFFAOYSA-N

assay

≥98.0% (HPLC)
≥98.0%

form

solid

ign. residue

≤0.1%

loss

≤0.2% loss on drying

bp

>286 °C/1.013 hPa

mp

60-62 °C

solubility

water: 0.87 g/L at 22 °C

density

1.4 g/cm3 at 23 °C

functional group

carboxylic acid
disulfide

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... ACHE(43), BCHE(590)
rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413)

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Application

(±)-α-Lipoic acid has been used:

  • In in vitro lipoylation studies and in the pyruvate dehydrogenase complex (PDC)-pyruvate dehydrogenase kinase (PDHK) functional assay.[1]
  • To investigate its antioxidative effect on developing cerebellum of rats exposed to arsenic during postnatal period.[2]

Biochem/physiol Actions

(±)-α-Lipoic acid exhibits direct free radical scavenging property[3] and reduces the increased oxidative stress.[4] In addition, it might also exhibit prooxidant activity.[3] α-Lipoic acid functions as an important prosthetic group in α-keto acid dehydrogenase complexes of the mitochondria.[5] It acts as a potential therapeutic for diabetic patients with distal symmetric polyneuropathy (DSP).[4] α-Lipoic acid is also used in the treatment of energy-impaired and redox unbalanced diseases.[5]
Antioxidant and coenzyme needed for the activity of enzyme complexes such as pyruvate dehydrogenase and glycine decarboxylase.
Antioxidant and coenzyme needed for the activity of enzyme complexes such as those of pyruvate dehydrogenase and glycine decarboxylase. Exogenous thioctic acid is reduced intracellularly by two or more enzymes. The reduced form then influences a number of cell processes by direct radical scavenging, recycling of other antioxidants, increasing glutathione synthesis, and modulating transcription factor activity particularly that of NF-κB. Decreases the phagocytosis of myelin by macrophages.

General description

α-lipoic acid (ALA, thioctic acid) is a natural organosulfur compound produced in plants, animals and humans. It is a powerful antioxidant and plays a role in the forming nucleic acids, building blocks of DNA.[6]

This product is a racemic mixture.
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Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Klasa składowania

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Wybierz jedną z najnowszych wersji:

Certyfikaty analizy (CoA)

Lot/Batch Number
WXBF7281V
WXBF6450V
WXBF5862V
WXBF5783V
WXBF5133V

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

Insights on the Use of ?-Lipoic Acid for Therapeutic Purposes
Salehi B., et. al.
Biomolecules, 9(8), 356-356 (2019)
M. Koike et al.
Antibiotics, Vitamins and Hormones, 112-112 (1977)
Component co-expression and purification of recombinant human pyruvate dehydrogenase complex from baculovirus infected SF9 cells
Jiang Y, et al.
Protein Expression and Purification, 97, 9-16 (2014)
Ameliorative role of antioxidant supplementation on sodium-arsenite induced adverse effects on the developing rat cerebellum
Kaushal P, et al.
Journal of Ayurveda and integrative medicine (2019)
Catherine Grogan et al.
Sensors (Basel, Switzerland), 20(3) (2020-02-12)
The high sensitivity of silicon microcantilever sensors has expanded their use in areas ranging from gas sensing to bio-medical applications. Photochromic molecules also represent promising candidates for a large variety of sensing applications. In this work, the operating principles of
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Produkty

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Questions

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  1. 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

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  2. 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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