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Lipoic acid

HCID 6112
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
1200-22-2
표준 SMILES
O=C(O)CCCC[C@@H]1CCSS1
InChIKey
AGBQKNBQESQNJD-SSDOTTSWSA-N
분자식
C8H14O2S2
평균 분자량
206.3 g/mol
단동위원소 질량
206.04352169

개요

(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.

이름 및 식별자

우선 이름
Lipoic acid
IUPAC
5-[(3R)-dithiolan-3-yl]pentanoic acid
영어명
(R)-Lipoic acid
분자식
C8H14O2S2
분자량
206.33

이름 및 동의어

lipoic acid(R)-lipoic acid(R)-5-(1,2-Dithiolan-3-yl)pentanoic acid(R)-alpha-Lipoic acidD-Thioctic acid(R)-(+)-1,2-Dithiolane-3-pentanoic acidR-(+)-Thioctic acid(+)-alpha-Lipoic acid1,2-Dithiolane-3-pentanoic acid, (3R)-R-alpha-Lipoic acidThioctic acid d-form5-[(3R)-dithiolan-3-yl]pentanoic acid
이름 더 보기
ipoic acidTiobe(R)-(+)-α
BerlitionThiogammaLipoecTiobec5-[(3R)-1,2-dithiolan-3-yl]pentanoic acidR-Lipoic acid(R)-(+)-lipoic acid(R)-1,2-Dithiolane-3-pentanoic acid

데이터베이스 식별자

CAS
1200-22-2、62-46-4
PubChem CID
6112
DTXSID
DTXSID20152651
ChEBI
CHEBI:30314
UNII
VLL71EBS9Z
Nikkaji
J9.331I

물성

구조 계산 물성보충 중

XLogP
1.7
극성 표면적
87.9 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
12
형식 전하
0
복잡도
150

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Thia fatty acids [FA0113]
SpringerMaterials PropertiesCrystal structure
SolubilityInsoluble
Melting Point60.5 °C
Physical DescriptionSolid

물리화학적 성질

녹는점
48 · 48-52 °C(lit.)
끓는 점
185 · 185-195 °C(Press: 0.5 Torr)
밀도
1.218 · 1.218±0.06 g/cm3(Predicted)
굴절률
114 ° · 114 ° (C=1, EtOH)
인화점
230 °F · >230 °F
저장 조건
-20 °C · -20°C
용해도
아세토니트릴(약간), 클로로포름(약간), DMSO 에 용해됨
물리적 상태
고체
산도 계수 (pKa)
5.4 · 5.4(at 25℃)
색상
밝은 노란색에서 노란색까지
Merck
14 · 14,9326
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
SMILES
OC(=O)CCCC[C@@H]1CCSS1 || OC(=O)CCCC[C@@H]1CCSS1
LogP
2.16 · 2.160 (est)

화학적 성질

Yellow Crystalline Solid

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

wgk
3
HS 번호
29349990
risk_code
22-36/38
safety_code
20-36-26-35
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

Pharmacodynamics · 1건

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 · 1건

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.

Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency

응용 분야

용도A fat-metabolism stimulator

일반 설명α-Lipoic acid is an antioxidant which is generally present in plants, animals and many other microorganisms.

상·하류 제품 정보

하류 제품

6,8-디설파닐옥타노익산

관련 반응

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