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α-Lipoic acid

α-Lipoic acid structure

CAS No:
1200-22-2
Formula:
C8H14O2S2
Chemical Name:
α-Lipoic acid
Synonyms:
1,2-Dithiolane-3-pentanoic acid,(3R)-;1,2-Dithiolane-3-valeric acid,(+)-;1,2-Dithiolane-3-pentanoic acid,(R)-;(3R)-1,2-Dithiolane-3-pentanoic acid;d-Thioctic acid;(R)-(+)-α-Lipoic acid;α-(+)-Lipoic acid;α-Lipoic acid;Lipoic acid;(R)-α-Lipoic acid;(R)-Lipoic acid;R-(+)-Thioctic acid;Tiobec;Thiogamma;Byodinoral 300;Tiobec Retard;Lipoec;Berlition;Thioderm;alpha-Lipoic acid;Destior-R;Matris thioctic;(R)-(+)-1,2-Dithiolane-3-pentanoic acid;(R)-5-(1,2-Dithiolan-3-yl)pentanoicacid;Arlipoic acid;57828-26-9;2087491-16-3
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Lipoic acid ((R)-(+)-α-Lipoic acid) is an antioxidant, which is an essential cofactor of mitochondrial enzyme complexes. (R)-(+)-α-Lipoic acid is more effective than racemic Lipoic acid.

Solid

(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 prosthetic group, a nutraceutical and a cofactor. It is a lipoic acid, a member of dithiolanes, a heterocyclic fatty acid and a thia fatty acid. It derives from an octanoic acid. It is a conjugate acid of a (R)-lipoate. It is an enantiomer of a (S)-lipoic acid.|A vitamin-like antioxidant.|An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.

α-Lipoic acid Basic Attributes

Molecular Weight：

206.33

Exact Mass：

206.33

EC Number：

200-534-6

UNII：

VLL71EBS9Z

DSSTox ID：

DTXSID20152651

HScode：

2934999090

Characteristics

PSA：

87.9

XLogP3：

1.7

Appearance：

Solid

Density：

1.2±0.1 g/cm3

Melting Point：

46-48 °C

Boiling Point：

185-195 °C @ Press: 0.5 Torr

Flash Point：

173.0±19.3 °C

Refractive Index：

1.562

Water Solubility：

2.24e-01 g/L

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

Precautionary statement(s)：

P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 122 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug 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.

MeSH：

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

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.

MeSH Entry Terms：

Acid, alpha-Lipoic

α-Lipoic acid Use and Manufacturing

Use Classification：

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Thia fatty acids [FA0113]

Computed Properties

Molecular Weight:206.3
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:206.04352203
Monoisotopic Mass:206.04352203
Topological Polar Surface Area:87.9
Heavy Atom Count:12
Complexity:150
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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