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

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

Product Name:
(R)-(+)-1,2-Dithiolane-3-pentanoic acid
Synonyms:
  • 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
  • 5-[(3R)-dithiolan-3-yl]pentanoic acid
  • 5-[(3R)-dithiolan-3-yl]valeric acid
  • (R)-(+)-1,2-Dithiola
  • (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
  • (R)-Thioctic Acid (R)-1,2-Dithiolane-3-valeric Acid
  • D-lipoic acid
  • (R)-(+)-1,2-Dithiolane-3-pentanoic acid 97%
CAS:
1200-22-2
MF:
C8H14O2S2
MW:
206.33
EINECS:
638-752-2
Product Categories:
  • API
  • Sulfur & Selenium Compounds
  • Chiral Reagents
  • Chiral Building Blocks
  • Heterocyclic Building Blocks
  • Others
  • FINE Chemical & INTERMEDIATES
  • Heterocycles
  • 1200-22-2
Mol File:
1200-22-2.mol
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(R)-(+)-1,2-Dithiolane-3-pentanoic acid Chemical Properties

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
optical activity
[α]20/D +104°, c = 1 in chloroform
Merck 
14,9326
LogP
2.160 (est)
CAS DataBase Reference
1200-22-2(CAS DataBase Reference)
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Safety Information

Risk Statements 
22-36/38
Safety Statements 
20-36-26-35
WGK Germany 
3
HS Code 
29349990

MSDS

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

Chemical Properties

Yellow Crystalline Solid

Uses

A fat-metabolism stimulator

Uses

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.

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.

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