基本情報
- 標準SMILES
O=C(O)CCCC[C@@H]1CCSS1- InChIKey
AGBQKNBQESQNJD-SSDOTTSWSA-N- 分子式
- C8H14O2S2
- 平均分子量
- 206.3 g/mol
- 単同位体質量
- 206.04352169
概要
(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 cofactor, a prosthetic group and a nutraceutical. 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.
名称と識別子
- 優先名称
- Lipoic acid
- IUPAC
- 5-[(3R)-dithiolan-3-yl]pentanoic acid
名称と別名
名称をさらに表示
データベース識別子
- CAS
1200-22-2、62-46-4- PubChem CID
- 6112
- DTXSID
DTXSID20152651- ChEBI
CHEBI:30314- UNII
- VLL71EBS9Z
- Nikkaji
- J9.331I
物性
構造計算による物性
- XLogP
- 1.7
- 極性表面積
- 87.9 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 4
- 回転可能結合数
- 5
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 150
実験および物理化学的性質
化学と産業
薬理情報
Pharmacodynamics
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. Since DMSA cannot cross the blood-brain barrier, both lipoic acid and DMSA tend to be used together. 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.
Mechanism of Action
Lipoic Acid is generally involved in oxidative decarboxylations of keto acids and is presented as a growth factor for some organisms. Lipoic acid exists as two enantiomers, the R-enantiomer and the S-enantiomer. Normally only the R-enantiomer of an amino acid is biologically active, but for lipoic acid the S-enantiomer assists in the reduction of the R-enantiomer when a racemic mixture is given. Some recent studies have suggested that the S-enantiomer in fact has an inhibiting effect on the R-enantiomer, reducing its biological activity substantially and actually adding to oxidative stress rather than reducing it. Furthermore, the S-enantiomer has been found to reduce the expression of GLUT-4s in cells, responsible for glucose uptake, and hence reduce insulin sensitivity.
関連反応
関連ノート
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