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Dihydrolipoic acid

Cat No.:V12123 Purity: ≥98%
Dihydrolipoic Acid (DHLA) is an extremely effective antioxidant that scavenges almost all oxygen-centered free radicals.
Dihydrolipoic acid
Dihydrolipoic acid Chemical Structure CAS No.: 462-20-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Dihydrolipoic Acid (DHLA) is an extremely effective antioxidant that scavenges almost all oxygen-centered free radicals. Dihydrolipoic Acid displays anti~inflammatory properties in a variety of diseases. Dihydrolipoic Acid exerts a preventive effect in rats with LPS-induced disease behavior through the ERK/Nrf2/HO-1/ROS/NLRP3 pathway. Dihydrolipoic Acid may be utilized in depression research.
Dihydrolipoic acid (DHLA, CAS# 462-20-4) is the reduced form of lipoic acid and a thio-fatty acid. It is a potent antioxidant that can directly destroy superoxide, hydroperoxy, and hydroxyl radicals. DHLA also exhibits neuroprotective and anti-tumor effects and is a human metabolite. It is known for its anti-inflammatory properties and its ability to scavenge almost all oxygen-centered free radicals.
Biological Activity I Assay Protocols (From Reference)
Targets
Dihydrolipoic acid acts as a general antioxidant, scavenging a variety of reactive oxygen species (ROS) including hydroxyl radicals, peroxynitrite, hydrogen peroxide, and hypochlorite. It targets oxidative stress pathways and can modulate cellular redox status. DHLA has been shown to exert its preventive effects in LPS-induced disease behavior in rats through the ERK/Nrf2/HO-1/ROS/NLRP3 pathway. It also functions as a neuroprotective agent.
ln Vitro
There is an antioxidant in dihydrolipoic acid. At a rate of around 3.3×105 M-1 s-1, DHLA may scavenge OH radicals and superoxide dilution. Dihydrolipoic acid is a highly effective antioxidant, which is crucial as O2-is a more selective alternation that is quite mild and may be utilized to differentiate between substrates' varying levels of antioxidant capacity [1].
In vitro, dihydrolipoic acid exhibits potent antioxidant activity, as demonstrated by its ability to inhibit LDL oxidation and scavenge DPPH radicals. It has been shown to raise ROS and NO levels and activate caspase-9 and caspase-3 in certain contexts. DHLA displays anti-inflammatory properties in various disease models. It is a potent antioxidant proven to directly scavenge superoxide anions, hydroperoxide radicals, and hydroxyl radicals.
ln Vivo
Treatment with dihydrolipoic acid (DHLA) can stop LPS-induced sickness behavioral episodes. In LPS-induced illness behavior events, dihydrolipoic acid decreased the expression of NLRP3, caspase-1, and IL-1β and raised the expression of ERK, Nrf2, and HO-1. However, it decreased the quantity of ROS formation. Alpha-lipoic acid (LA), which decreases oxidation and functions as a potent antioxidant, is converted to dihydrolipoic acid [2]. Treatment with dihydrolipoic acid can reverse illness behavior brought on by LPS [2].
In vivo, dihydrolipoic acid has been shown to exert preventive effects in LPS-induced disease behavior in rats through the ERK/Nrf2/HO-1/ROS/NLRP3 pathway. It has been used in research related to depression and exhibits neuroprotective and anti-tumor effects. Its antioxidant properties contribute to its protective effects in various animal models of disease.
Enzyme Assay
The antioxidant activity of dihydrolipoic acid can be assessed using cell-free assays such as the DPPH radical scavenging assay, the ABTS radical cation decolorization assay, and the ferric reducing antioxidant power (FRAP) assay. In these assays, the compound is incubated with the respective radicals or oxidants, and the decrease in absorbance is measured spectrophotometrically to determine the scavenging capacity or reducing power.
Cell Assay
The cellular antioxidant activity of dihydrolipoic acid can be evaluated using cell-based models of oxidative stress. Cells such as neurons or hepatocytes are pre-treated with DHLA and then exposed to an oxidative stressor like hydrogen peroxide or menadione. Cell viability, ROS levels, and markers of oxidative damage (e.g., lipid peroxidation, protein carbonylation) are measured. The protective effects of DHLA against oxidative stress-induced cell death are quantified.
Animal Protocol
Animal/Disease Models: Adult male SD (SD (Sprague-Dawley)) rat (body weight, 200-220 g) [2]
Doses: 15 mg/kg, 30 mg/kg , 60 mg/kg
Route of Administration: Daily intraperitoneal (ip) injection
Experimental Results: Treatment with 30 mg/kg and 60 mg/kg improved body weight gain compared with the LPS group.
In vivo studies of dihydrolipoic acid often involve animal models of disease where oxidative stress plays a role. For example, in LPS-induced disease behavior models, rats are treated with DHLA, and behavioral changes, as well as biochemical markers of inflammation and oxidative stress in the brain, are assessed. The compound is typically administered via oral gavage or intraperitoneal injection.
ADME/Pharmacokinetics
Dihydrolipoic acid has a molecular weight of 208.34 and a formula of C8H16O2S2. It is a thio-fatty acid that is the reduced form of lipoic acid. Its antioxidant properties are attributed to its two thiol groups, which can directly scavenge free radicals.
Toxicity/Toxicokinetics
Dihydrolipoic acid is generally considered safe and is a naturally occurring human metabolite. It has been used in research at concentrations ranging from 0.01 to 0.5 mM for antioxidant studies. At higher concentrations (50-100 µM), it exhibits various biological effects. Specific toxicity data in animal models are not detailed in the available literature, but its status as an endogenous compound suggests a favorable safety profile.
References

[1]. Lipoic acid and dihydrolipoic acid. A comprehensive theoretical study of their antioxidant activity supported by available experimental kinetic data. J Chem Inf Model. 2014 Jun 23;54(6):1642-52.

[2]. Dihydrolipoic acid protects against lipopolysaccharide-induced behavioral deficits and neuroinflammation via regulation of Nrf2/HO-1/NLRP3 signaling in rat. J Neuroinflammation. 2020 May 25;17(1):166.

Additional Infomation
Dihydrolipoic acid (DLA) is a thiocarboxylic acid, the reduced form of lipoic acid. It is a potent antioxidant, proven to directly scavenge superoxide anions, hydroperoxide radicals, and hydroxyl radicals; it also possesses neuroprotective and antitumor effects. It is a neuroprotective agent, an antioxidant, and a human metabolite. Its function is related to octanoic acid; it is the conjugate acid of dihydrolipoic acid ester. There are reports and data regarding the presence of DLA in the human body.
Dihydrolipoic acid is the reduced form of lipoic acid, a dietary supplement and cofactor for mitochondrial enzymes. It has been investigated for its potential therapeutic applications in conditions associated with oxidative stress, including neurodegenerative diseases, diabetes, and inflammation. It is not an approved drug but is widely used as a research tool and dietary supplement.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H16O2S2
Molecular Weight
208.34144
Exact Mass
208.059
CAS #
462-20-4
PubChem CID
421
Appearance
Colorless to light yellow liquid
Density
1.1±0.1 g/cm3
Boiling Point
360.8±32.0 °C at 760 mmHg
Melting Point
60ºC
Flash Point
172.0±25.1 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.527
LogP
2.07
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Heavy Atom Count
12
Complexity
128
Defined Atom Stereocenter Count
0
SMILES
C(CCC(=O)O)CC(CCS)S
InChi Key
IZFHEQBZOYJLPK-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
Chemical Name
6,8-bis(sulfanyl)octanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~479.98 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.83 mg/mL (3.98 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 0.83 mg/mL (3.98 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 0.83 mg/mL (3.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.7998 mL 23.9992 mL 47.9985 mL
5 mM 0.9600 mL 4.7998 mL 9.5997 mL
10 mM 0.4800 mL 2.3999 mL 4.7998 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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