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HomeProduct name list(R)-(+)-1,2-Dithiolane-3-pentanoic acid

(R)-(+)-1,2-Dithiolane-3-pentanoic acid

Synonym(s):(R)-(+)-1,2-Dithiolane-3-pentanoic acid;(R)-6,8-Dithiooctanoic acid;(R)-6,8-Thioctic acid

  • CAS NO.:1200-22-2
  • Empirical Formula: C8H14O2S2
  • Molecular Weight: 206.33
  • MDL number: MFCD01631142
  • EINECS: 638-752-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 08:26:49
(R)-(+)-1,2-Dithiolane-3-pentanoic acid Structural

What is (R)-(+)-1,2-Dithiolane-3-pentanoic acid?

Chemical properties

Yellow Crystalline Solid

The Uses of (R)-(+)-1,2-Dithiolane-3-pentanoic acid

A fat-metabolism stimulator

The Uses of (R)-(+)-1,2-Dithiolane-3-pentanoic acid

α-Lipoic acid has been used as a reference standard for the analysis of α-lipoic acid in human plasma by high performance liquid chromatography coupled to electron capture detector (HPLC-ECD), in various food matrices and dietary supplements by HPLC combined with coulometric electrode array detector (CEAD) as well as electrospray ionization mass spectrometer (ESI-MS).
It may be used as a reference standard for the determination of α-lipoic acid in human urine by isocratic reversed-phase HPLC and in α-lipoic acid capsules by HPLC with chemiluminescence detection.

Indications

For nutritional supplementation, also for treating dietary shortage or imbalance.

Background

A vitamin-like antioxidant.

What are the applications of Application

(+)-α-Lipoic acid is An antioxidant

Definition

ChEBI: (R)-lipoic acid is the (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties. It has a role as a prosthetic group, a nutraceutical and a cofactor. It is a lipoic acid, a member of dithiolanes, a heterocyclic fatty acid and a thia fatty acid. It is functionally related to an octanoic acid. It is a conjugate acid of a (R)-lipoate. It is an enantiomer of a (S)-lipoic acid.

General Description

α-Lipoic acid is an antioxidant which is generally present in plants, animals and many other microorganisms.

Biochem/physiol Actions

(R)-(+)-α-Lipoic acid was shown to significantly increase pyruvate oxidation while abrogating fatty acid oxidation in rat hepatocytes. These effects make R-(+)-α-Lipoic acid a promising treatment option for the treatment of Type II diabetes. It is a biological antioxidant with prooxidant activities, its therapeutic potential is widely investigated, e.g. in the treatment for Alzheimer′s disease.

Pharmacokinetics

Lipoic acid (or α-lipoic acid) is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Neither DMSA nor MSM can cross the blood-brain barrier, which is why both lipoic acid and DMSA are used. It is hypothesized that this treatment-along with carnitine, dimethylglycine (DMG), Vitamin B6, folic acid, and magnesium—could be used to treat autism and amalgam poisoning. In this hypothesis, the reason why autism is difficult to treat is that mercury is attached to the brain cells and most medicines and vitamin supplements do not penetrate the blood-brain barrier. However, α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.

Metabolism

Not Available

Properties of (R)-(+)-1,2-Dithiolane-3-pentanoic acid

Melting point: 48-52 °C(lit.)
Boiling point: 185-195 °C(Press: 0.5 Torr)
alpha  D23 +104° (c = 0.88 in benzene)
Density  1.218±0.06 g/cm3(Predicted)
refractive index  114 ° (C=1, EtOH)
Flash point: >230 °F
storage temp.  -20°C
solubility  Acetonitrile (Slightly), Chloroform (Slightly), DMSO
form  Solid
pka 5.4(at 25℃)
color  Light Yellow to Yellow Low-Melting
optical activity [α]20/D +104°, c = 1 in chloroform
Merck  14,9326
CAS DataBase Reference 1200-22-2(CAS DataBase Reference)

Safety information for (R)-(+)-1,2-Dithiolane-3-pentanoic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P501:Dispose of contents/container to..…

Computed Descriptors for (R)-(+)-1,2-Dithiolane-3-pentanoic acid

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