119365-69-4

Basic information

• Product Name: (R)-6,8-Dimercaptooctanoic acid
• Synonyms: R-(+)-Dihydrolipoic acid;(R)-6,8-Dimercaptooctanoic acid
• CAS NO: 119365-69-4
• Molecular Formula: C₈H₁₆O₂S₂
• Molecular Weight: 208.34144
• Mol File: 119365-69-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 361°C
• Flash Point: 172°C
• Appearance: /
• Density: 1.134
• PKA: 4.74±0.10(Predicted)
• CAS DataBase Reference: (R)-6,8-Dimercaptooctanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-6,8-Dimercaptooctanoic acid(119365-69-4)
• EPA Substance Registry System: (R)-6,8-Dimercaptooctanoic acid(119365-69-4)

Safety Data

• Hazardous Substances Data: 119365-69-4(Hazardous Substances Data)

Usage

General Description

(R)-6,8-Dimercaptooctanoic acid, also known as DMSA, is a chelating agent commonly used in the treatment of heavy metal poisoning. It works by binding with heavy metals such as lead, mercury, and arsenic in the body, and helping to remove them from the system through urine excretion. DMSA has been found to be particularly effective in treating lead poisoning in children, and is also used as a treatment for mercury poisoning in adults. Additionally, DMSA has been studied for its potential antioxidant and anti-inflammatory properties, and has shown promise in the treatment of certain neurological disorders such as autism and Parkinson's disease. Overall, DMSA is an important therapeutic agent in the management of heavy metal toxicity and related conditions.

Synthetic route

(R)-1,2-dithiolane-3-pentanoic acid (1200-22-2) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 1h;	100%
With 1,4-dihydronicotinamide adenine dinucleotide; porcine heart dihydrolipoamide dehydrogenase at 35℃; Enzyme kinetics;
With sodium borohydrid In water; toluene

Thioctic acid (1077-28-7, 62-46-4) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
With sodium borate; sodium hydrogencarbonate

(R)-8-hydroxy-6-mercapto-octanoic acid (101567-87-7) + thiourea (17356-08-0) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
With hydrogen bromide anschliessend mit wss. Natronlauge;

(R)-6,8-Bis-acetylsulfanyl-octanoic acid ethyl ester → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
With phosphate buffer pH 7.0; wheatgerm lipase

Methyl (6R)-6,8-diacetyldihydrolipoate (240414-07-7) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
With potassium hydroxide; water at 20℃; for 6h; Hydrolysis;

methyl adipoyl chloride (35444-44-1) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: pyridine / CH2Cl2 / 4 h / 20 °C 2: CH2Cl2 / 3 h / 60 °C 3: yeast; EtOH; NaCl / H2O / 37 °C / pH 6.0 / Microbiological reaction 4: 72 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 5: Et3N / CH2Cl2 / 1 h / 0 °C 6: dimethylformamide; cyclohexane / 4 h / 50 °C 7: H2O; KOH / 6 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1: Ca(OH)2 / CH2Cl2 / 2 h / Heating 2: NH3; H2O / CH2Cl2 / 3 h / 25 °C / pH 9 3: H2 / Ru2Cl4[(S)-BINAP]2*Et3N / methanol / 12 h / 80 °C / 22.5 Torr 4: 82 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 5: Et3N / CH2Cl2 / 1 h / 0 °C 6: dimethylformamide; cyclohexane / 4 h / 50 °C 7: H2O; KOH / 6 h / 20 °C View Scheme

(6S)-(-)-methyl 6,8-dihydroxyoctanoate (116349-04-3) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 1 h / 0 °C 2: dimethylformamide; cyclohexane / 4 h / 50 °C 3: H2O; KOH / 6 h / 20 °C View Scheme

(6S)-(+)-methyl 6,8-bis(methylsulfonyloxy)octanoate (116349-05-4) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide; cyclohexane / 4 h / 50 °C 2: H2O; KOH / 6 h / 20 °C View Scheme
Stage #1: (6S)-(+)-methyl 6,8-bis(methylsulfonyloxy)octanoate With sodium sulfide; sulfur In methanol Stage #2: With sodium hydroxide; sodium tetrahydroborate In methanol; water Stage #3: With methanol; sulfuric acid; water pH=4;

3-oxo-1,8-octanoic acid dimethyl ester (87342-98-1) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: H2 / Ru2Cl4[(S)-BINAP]2*Et3N / methanol / 12 h / 80 °C / 22.5 Torr 2: 82 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 3: Et3N / CH2Cl2 / 1 h / 0 °C 4: dimethylformamide; cyclohexane / 4 h / 50 °C 5: H2O; KOH / 6 h / 20 °C View Scheme

(3S)-3-hydroxyoctanedioic acid dimethyl ester (142886-33-7) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 2: Et3N / CH2Cl2 / 1 h / 0 °C 3: dimethylformamide; cyclohexane / 4 h / 50 °C 4: H2O; KOH / 6 h / 20 °C View Scheme

1-O-Isobutyl 8-O-methyl 3-oxooctanedioate (142886-30-4) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: yeast; EtOH; NaCl / H2O / 37 °C / pH 6.0 / Microbiological reaction 2: 72 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 3: Et3N / CH2Cl2 / 1 h / 0 °C 4: dimethylformamide; cyclohexane / 4 h / 50 °C 5: H2O; KOH / 6 h / 20 °C View Scheme

1-O-Isobutyl 8-O-methyl (3S)-3-hydroxyoctanedioate (142886-36-0) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 72 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 2: Et3N / CH2Cl2 / 1 h / 0 °C 3: dimethylformamide; cyclohexane / 4 h / 50 °C 4: H2O; KOH / 6 h / 20 °C View Scheme

2-[1-Hydroxy-eth-(E)-ylidene]-3-oxo-octanedioic acid dimethyl ester → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: NH3; H2O / CH2Cl2 / 3 h / 25 °C / pH 9 2: H2 / Ru2Cl4[(S)-BINAP]2*Et3N / methanol / 12 h / 80 °C / 22.5 Torr 3: 82 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 4: Et3N / CH2Cl2 / 1 h / 0 °C 5: dimethylformamide; cyclohexane / 4 h / 50 °C 6: H2O; KOH / 6 h / 20 °C View Scheme

6-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-6-hydroxy-hexanoic acid methyl ester (212693-39-5) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: CH2Cl2 / 3 h / 60 °C 2: yeast; EtOH; NaCl / H2O / 37 °C / pH 6.0 / Microbiological reaction 3: 72 percent / NaBH4 / tetrahydrofuran / 3 h / Heating 4: Et3N / CH2Cl2 / 1 h / 0 °C 5: dimethylformamide; cyclohexane / 4 h / 50 °C 6: H2O; KOH / 6 h / 20 °C View Scheme

(E)-(S)-6,8-Bis-acetylsulfanyl-oct-4-enoic acid ethyl ester → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2, (PPh3)3RhCl 2: phosphate buffer pH 7.0, wheatgerm lipase View Scheme

(R)-3-acetylsulfanyl-octanedioic acid-8-ethyl ester (102954-14-3) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride 2: sodium borate; dioxane / beim Erwaermen des Reaktionsprodukts mit wss.-methanol. Natronlauge und wenig Zink-Pulver 3: aqueous hydrobromic acid / anschliessend mit wss. Natronlauge View Scheme

(R)-3-acetylsulfanyl-octanedioic acid-8-ethyl ester-1-chloride (104665-85-2) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borate; dioxane / beim Erwaermen des Reaktionsprodukts mit wss.-methanol. Natronlauge und wenig Zink-Pulver 2: aqueous hydrobromic acid / anschliessend mit wss. Natronlauge View Scheme

(S)-lipoic acid (62-46-4, 1077-27-6, 1077-28-7, 1200-22-2, 52578-51-5) → (R)-6,8-dimercaptooctanoic acid (119365-69-4)

Conditions	Yield
With sodium borohydrid In water; toluene

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + 5-hydroxynaphtho-1,4-quinone (481-39-0) → 5-(2',3'-dihydrospiro[1,3-dithiane-2,3'-[5]hydroxy[1,4]naphthoquinon-4-yl])pentanoic acid (1233347-82-4)

Conditions	Yield
Stage #1: (R)-6,8-dimercaptooctanoic acid; 5-hydroxynaphtho-1,4-quinone With triethylamine In ethanol for 0.166667h; Stage #2: With trifluoroacetic acid In ethanol	44%

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + [1,4]naphthoquinone (130-15-4) → 5-(2H-3,4-dihydro-6,11-dioxonaphtho[2,3-b][1,4]dithiepin-2-yl)pentanoic acid (1233347-83-5)

Conditions	Yield
Stage #1: (R)-6,8-dimercaptooctanoic acid; [1,4]naphthoquinone With triethylamine In ethanol for 0.166667h; Stage #2: With trifluoroacetic acid In ethanol	44%

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + 5,8-Dihydroxy-1,4-naphthoquinone (475-38-7) → 5-(2H-3,4-dihydro-7,10-dihydroxy-6,11-dioxonaphtho[2,3-b][1,4]dithiepin-2-yl)pentanoic acid (1233347-84-6)

Conditions	Yield
Stage #1: (R)-6,8-dimercaptooctanoic acid; 5,8-Dihydroxy-1,4-naphthoquinone With triethylamine In ethanol for 0.166667h; Stage #2: With trifluoroacetic acid In ethanol	25%

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + menadione (58-27-5) → 5-(2',3'-dihydrospiro[1,3-dithiane-2,3'-[2]methyl[1,4]naphthoquinon-4-yl])pentanoic acid + C30H28O6S2 (1233347-87-9)

Conditions	Yield
With triethylamine In ethanol for 2h;	A 20% B 16%

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + bis-(4-dimethylamino-phenyl)-carbodiimide (738-65-8) → N-((R)-6,8-dimercapto-octanoyl)-N,N'-bis-(4-dimethylamino-phenyl)-urea

Conditions	Yield
With diethyl ether

(R)-6,8-dimercaptooctanoic acid (119365-69-4) → (R)-1,2-dithiolane-3-pentanoic acid (1200-22-2)

Conditions	Yield
With iron(III) chloride; potassium carbonate
With chloroform; iodine; potassium iodide
With mushroom tyrosinase

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + lithium- → (R)-6-acetylsulfanyl-8-mercapto-octanoic acid (91007-40-8)

Conditions	Yield
With enzyme-substance from escherichia coli

(R)-6,8-dimercaptooctanoic acid (119365-69-4) → (R)-6-acetylsulfanyl-8-mercapto-octanoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: enzyme-substance from escherichia coli 2: benzene View Scheme

(R)-6,8-dimercaptooctanoic acid (119365-69-4) → N-((R)-6-acetylsulfanyl-8-mercapto-octanoyl)-N,N'-bis-(4-dimethylamino-phenyl)-urea

Conditions	Yield
Multi-step reaction with 2 steps 1: enzyme-substance from escherichia coli 2: diethyl ether; petroleum ether View Scheme

(R)-6,8-dimercaptooctanoic acid (119365-69-4) → N-((R)-8-acetylsulfanyl-6-mercapto-octanoyl)-N,N'-bis-(4-dimethylamino-phenyl)-urea

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: pyridine View Scheme

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + 5-hydroxynaphtho-1,4-quinone (481-39-0) → 5-(2H-3,4-dihydro-7-hydroxy-6,11-dioxonaphtho[3,2-b][1,4]dithiepin-2-yl)pentanoic acid (1233347-80-2) + 5-(2H-3,4-dihydro-7-hydroxy-6,11-dioxonaphtho[2,3-b][1,4]dithiepin-4-yl)pentanoic acid (1233347-81-3)

Conditions	Yield
With triethylamine In ethanol for 0.166667h;

(R)-6,8-dimercaptooctanoic acid (119365-69-4) + juglone acetate (5196-28-1) → 5-(7-acetoxy-2H-3,4-dihydro-6,11-dioxonaphtho[3,2-b][1,4]dithiepin-2-yl)pentanoic acid (1233347-85-7) + 5-(7-acetoxy-2H-3,4-dihydro-6,11-dioxonaphtho[2,3-b][1,4]dithiepin-4-yl)pentanoic acid (1233347-86-8)

Conditions	Yield
With triethylamine In ethanol for 0.166667h;

Upstream product

• 462-20-4 dihydrolipoic acid 
• 71399-42-3 trans-2-(D-Arabino-1',2',3',4'-tetrahydroxybutyl)-1,3-dithianyl-4-valeric acid 
• 41443-60-1 (+)-6,8-dichloro-octanoic acid 
• 71399-42-3 cis-2-(D-Arabino-1',2',3',4'-tetrahydroxybutyl)-1,3-dithianyl-4-valeric acid 
• 62-46-4 (S)-lipoic acid 
• 104665-85-2 (R)-3-acetylsulfanyl-octanedioic acid-8-ethyl ester-1-chloride 
• 102954-14-3 (R)-3-acetylsulfanyl-octanedioic acid-8-ethyl ester 
• 212693-39-5 6-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-6-hydroxy-hexanoic acid methyl ester 
• 142886-36-0 1-O-Isobutyl 8-O-methyl (3S)-3-hydroxyoctanedioate 
• 142886-30-4 1-O-Isobutyl 8-O-methyl 3-oxooctanedioate 
• 142886-33-7 (3S)-3-hydroxyoctanedioic acid dimethyl ester 
• 87342-98-1 3-oxo-1,8-octanoic acid dimethyl ester 
• 116349-05-4 (6S)-(+)-methyl 6,8-bis(methylsulfonyloxy)octanoate 
• 116349-04-3 (6S)-(-)-methyl 6,8-dihydroxyoctanoate 

Downstream Products

• 62-46-4 (+)-Lipoic acid 
• 62-46-4 (-)-Lipoic acid 
• 1200-22-2 (R)-1,2-dithiolane-3-pentanoic acid 

Relevant articles and documents

Reaction of dihydrolipoic acid with juglone and related naphthoquinones: unmasking of a spirocyclic 1,3-dithiane intermediate en route to naphtho[1,4]dithiepines

The reaction of dihydrolipoic acid (DHLA) with 5-hydroxy-1,4-naphthoquinone (juglone) gives rise to the novel naphtho[1,4]dithiepine derivatives through ring expansion of an unstable spirocyclic 1,3-dithiane intermediate, which was isolated and completely characterized. Reported herein is also the characterization of novel reaction products of DHLA with other naphthoquinones and the extension of the study to the spirocyclic adduct formed by reaction with a representative 2-substituted naphthoquinone.

Physicochemical Profiling of α-Lipoic Acid and Related Compounds

Lipoic acid, the biomolecule of vital importance following glycolysis, shows diversity in its thiol/disulfide equilibria and also in its eight different protonation forms of the reduced molecule. In this paper, lipoic acid, lipoamide, and their dihydro derivatives were studied to quantify their solubility, acid–base, and lipophilicity properties at a submolecular level. The acid–base properties are characterized in terms of six macroscopic, 12 microscopic protonation constants, and three interactivity parameters. The species-specific basicities, the pH-dependent distribution of the microspecies, and lipophilicity parameters are interpreted by various intramolecular effects, and contribute to understanding the antioxidant, chelate-forming, and enzyme cofactor behavior of the molecules observed.

Circularly polarized luminescence in chiral silver nanoclusters

Silver nanoclusters (NCs) capped with enantiomeric bidentate ligands exhibited mirror image circularly polarized luminescence (CPL) spectra with an anisotropy factor of 0.2%. Chirality in the ligand staples is most likely responsible for the induction of optical activity in the emissive state.