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1077-28-7 molecular structure
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5-(1,2-dithiolan-3-yl)pentanoic acid

ChemBase ID: 70549
Molecular Formular: C8H14O2S2
Molecular Mass: 206.32556
Monoisotopic Mass: 206.04352169
SMILES and InChIs

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

Cite this record

CBID:70549 http://www.chembase.cn/molecule-70549.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Donor LogD (pH = 5.5) 1.0948822 
LogD (pH = 7.4) -0.6761287  Log P 2.1137793 
Molar Refractivity 54.3714 cm3 Polarizability 21.431002 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true  Acid pKa 4.523468 
H Acceptors

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dimethyl Sulfoxide expand Show data source
ethanol: soluble50 mg/mL expand Show data source
Methanol expand Show data source
Apperance
Light-Yellow Solid expand Show data source
yellow powder expand Show data source
Melting Point
59-61°C expand Show data source
59-63°C expand Show data source
60-61°C expand Show data source
60-62 °C expand Show data source
Boiling Point
160-165°C expand Show data source
160-165°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
2-8°C expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
JP1192000 expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
22-36/37/38 expand Show data source
Safety Statements
26-36/37 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H301-H315-H319-H335 expand Show data source
H302 expand Show data source
GHS Precautionary statements
P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... ACHE(43), BCHE(590)rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413) expand Show data source
Purity
≥98.0% expand Show data source
≥98.0% (HPLC) expand Show data source
≥99% expand Show data source
≥99% (titration) expand Show data source
95+% expand Show data source
98% expand Show data source
98-99% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
cell culture tested expand Show data source
Ignition Residue
≤0.1% expand Show data source
Description
Oxidized form expand Show data source
Biological Source
synthetic expand Show data source
Loss on Drying
≤0.1% loss on drying, 20 °C (HV) expand Show data source
Empirical Formula (Hill Notation)
C8H14O2S2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02101138 external link
Purity: 98-99%
A hydrogen transferrin cofactor.
MP Biomedicals - 02194751 external link
Cell Culture Reagent
Purity: 98-99%
Sigma Aldrich - T1395 external link
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 external link
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 external link
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 external link
A fat-metabolism stimulator.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Plotzker, R., et al.: Am. J. Med. Sci., 283, 79 (1982)
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PATENTS

PATENTS

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INTERNET

INTERNET

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