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

• ChemBase编号: 51
• 分子式: C8H14O2S2
• 平均质量: 206.32556
• 单一同位素质量: 206.04352169
• SMILES: S1SCC[C@H]1CCCCC(=O)O
• Canonical SMILES: OC(=O)CCCC[C@H]1SSCC1
• InChI: InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
• InChIKey: AGBQKNBQESQNJD-SSDOTTSWSA-N

名称和登记号

名称

• IUPAC标准名: 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
• IUPAC传统名: lipoic acid
• 商标名: Heparlipon; Biletan; Thioctsan
• 别名: (R)-6,8-二硫辛酸; (R)-6,8-硫辛酸; (R)-(+)-1,2-二硫戊环基-3-戊酸; (R)-(+)-1,2-二硫戊环基-3-戊酸; (R)-(+)-α-硫辛酸; (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid; (R)-6,8-Dithiooctanoic acid; (R)-6,8-Thioctic acid; (R)-(+)-1,2-Dithiolane-3-pentanoic acid; (R)-(+)-1,2-Dithiolane-3-pentanoic acid; (R)-(+)-α-Lipoic acid; DL-6,8-DITHIOOCTANOIC ACID; α-Lipoic acid (alpha lipoic acid); 6,8-Dithiooctanoic acid; Lipoate; Thioctic acid; alpha-Lipoic acid; 1,2-Dithiolane-3R-pentanoic acid; Lipoic Acid

登记号

• CAS号: 1077-28-7; 62-46-4; 1200-22-2
• MDL号: MFCD01631142
• PubChem SID: 24881001; 160963514
• PubChem CID: 6112
• CHEBI ID: 30314
• ATC码: A16AX01
• CHEMBL: 134342
• Chemspider ID: 5886
• DrugBank ID: DB00166
• KEGG ID: C16241
• 医学主题词(MeSH): Lipoic+acid
• 维基百科标题: Lipoic_acid

理论计算性质

JChem

• Acid pKa: 4.523468
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.0948822
• LogD (pH = 7.4): -0.6761287
• Log P: 2.1137793
• 摩尔折射率: 54.3714 cm^3
• 极化性: 21.431002 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.75
• LOG S: -2.96
• 溶解度: 2.24e-01 g/l

分子性质

理化性质

• 溶解度: Insoluble; Soluble as sodium salt in water; Soluble in ethanol
• 外观: Yellow needle-like crystals
• 熔点: 48-52 °C(lit.)
• 闪点: >110 °C; >230 °F
• 比旋光度: [α]/D +115±5°, c = 1% in ethanol; [α]20/D +104°, c = 1 in chloroform
• 疏水性(logP): 2.1

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C; 2-8°C

药理学性质

• 生物利用度: 30% (oral)

产品相关信息

• 纯度: ≥98.0% (HPLC); 95+%; 97%
• 级别: analytical standard
• 光学纯度: enantiomeric excess: ≥98.0% (HPLC)
• 有效期: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C8H14O2S2
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 05214667

MP Biomedicals Rare Chemical collection

DrugBank - DB00166

• Drug Groups: approved; nutraceutical
• Description: A vitamin-like antioxidant. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• References: Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [Pubmed] ; REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 07039

Analysis Note
identity confirmed by LC-MS
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. 1

Sigma Aldrich - 579602

包装
1 g in glass bottle

参考文献

• Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. Pubmed
• REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. Pubmed