5-(1,2-dithiolan-3-yl)pentanoic acid

• ChemBase ID: 70549
• Molecular Formular: C8H14O2S2
• Molecular Mass: 206.32556
• Monoisotopic Mass: 206.04352169
• SMILES: C(=O)(CCCCC1SSCC1)O
• Canonical SMILES: OC(=O)CCCCC1SSCC1
• InChI: InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
• InChIKey: AGBQKNBQESQNJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(1,2-dithiolan-3-yl)pentanoic acid
• IUPAC Traditional name: 6,8-thioctic acid; thioctic acid dl-form
• Synonyms: (±)-1,2-Dithiolane-3-pentanoic acid; 6,8-Dithiooctanoic acid; DL-α-Lipoic acid; DL-6,8-Thioctic acid; Lip(S2); (±)-α-Lipoic acid; 5-(1,2-Dithiolan-3-yl)pentanoic acid; α-Lipoic acid; DL-THIOCTIC ACID; (+/-)-1,2-Dithiolane-3-pentanoic Acid; (+/-)-1,2-Dithiolane-3-valeric Acid; (+/-)-Thioctic Acid; (RS)-α-Lipoic Acid; DL-Thioctic Acid; Liposan; Lipothion; NSC 628502; NSC 90788; Protogen A; Thioctsan; Tioctacid; rac α-Lipoic Acid; 1,2-Dithiolane-3-valeric acid; DL-6,8-Dithiooctanoic acid; DL-Thioctic acid; (±)-1,2-二硫戊环基-3-戊酸; 6,8-二巯基辛酸; DL-α-硫辛酸; DL-6,8-硫辛酸; (±)-α-硫辛酸; DL-硫辛酸

Database IDs

• CAS Number: 1077-28-7
• EC Number: 214-071-2
• MDL Number: MFCD00005474
• Beilstein Number: 81853
• Merck Index: 149326
• PubChem SID: 162036264; 24278746; 24882156; 24899963
• PubChem CID: 864

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 1.0948822
• LogD (pH = 7.4): -0.6761287
• Log P: 2.1137793
• Molar Refractivity: 54.3714 cm^3
• Polarizability: 21.431002 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• Acid pKa: 4.523468
• H Acceptors: 2

PROPERTIES

Physical Property

• Solubility: Chloroform; Dimethyl Sulfoxide; ethanol: soluble50 mg/mL; Methanol
• Apperance: Light-Yellow Solid; yellow powder
• Melting Point: 59-61°C; 59-63°C; 60-61°C; 60-62 °C
• Boiling Point: 160-165°C; 160-165°C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: JP1192000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 22-36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

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

Product Information

• Purity: ≥98.0%; ≥98.0% (HPLC); ≥99%; ≥99% (titration); 95+%; 98%; 98-99%
• Suitability: cell culture tested
• Ignition Residue: ≤0.1%
• Description: Oxidized form
• Biological Source: synthetic
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV)
• Empirical Formula (Hill Notation): C8H14O2S2

DETAILS

MP Biomedicals - 02101138

Purity: 98-99%
A hydrogen transferrin cofactor.

MP Biomedicals - 02194751

Cell Culture Reagent
Purity: 98-99%

Sigma Aldrich - T1395

Other Notes
氧化形式
Biochem/physiol Actions
维持酶复合物（例如丙酮酸脱氢酶和甘氨酸脱羧酶的复合物）活性所需的抗氧化剂和辅酶。通过两种或多种酶的作用在细胞内还原外源性硫辛酸。然后，该还原形式通过直接清除自由基、循环利用其他抗氧化剂、增加谷胱甘肽的合成以及调控转录因子（尤其是 NF-κB）的活性而影响许多细胞过程。减少巨噬细胞对髓磷脂的吞噬。

Sigma Aldrich - 62320

Other Notes
Review1
Packaging
5, 25 g in glass bottle
Biochem/physiol Actions
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.

Sigma Aldrich - T5625

包装
1, 5, 25, 50 g in poly bottle
500 mg in poly bottle
Biochem/physiol Actions
维持酶复合物（例如丙酮酸脱氢酶和甘氨酸脱羧酶的复合物）活性所需的抗氧化剂和辅酶。通过两种或多种酶的作用在细胞内还原外源性硫辛酸。然后，该还原形式通过直接清除自由基、循环利用其他抗氧化剂、增加谷胱甘肽的合成以及调控转录因子（尤其是 NF-κB）的活性而影响许多细胞过程。减少巨噬细胞对髓磷脂的吞噬。

Toronto Research Chemicals - L468750

A fat-metabolism stimulator.

REFERENCES

• Plotzker, R., et al.: Am. J. Med. Sci., 283, 79 (1982)