Octanoic acid, 6,8-dimercapto- supplier

Name
DIHYDROLIPOIC ACID
EINECS
CAS No. 462-20-4
Article Data63
CAS DataBase
Density 1.134 g/cm³
Solubility
Melting Point 60ºC
Formula C₈H₁₆O₂S₂
Boiling Point 360.8 °C at 760 mmHg
Molecular Weight 208.346
Flash Point 172 °C
Transport Information
Appearance light yellow liquid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms (?à)-Dihydro-a-lipoic acid;(?à)-Dihydrolipoic acid;6,8-Dihydrothioctic acid;6,8-Dimercaptooctanoic acid;6,8-Dithiooctanoic acid;DL-Dihydro-a-lipoic acid;Dihydrolipoic acid;Dihydrothioctic acid;Reduced lipoic acid;Reduced thioctic acid;Thiocticacid, dihydro-;dl-Dihydrolipoic acid;a-Lipoic acid, dihydro-;g-Lipoic acid;
PSA 114.90000
LogP 2.24970

Synthetic route

: 1077-28-7, 62-46-4
Thioctic acid

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
With sodium tetrahydroborate; sodium hydrogencarbonate In water at 20℃; for 3h;	100%
Stage #1: Thioctic acid With sodium hydrogencarbonate In water Stage #2: With sodium tetrahydroborate In water at 0 - 20℃; for 1.33333h; Stage #3: With hydrogenchloride In water at 0℃; pH=1;	100%
With sodium tetrahydroborate; sodium hydrogencarbonate at 0℃; for 3h;	99.5%

: 1200-22-2
(R)-1,2-dithiolane-3-pentanoic acid

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium borohydrid; sodium hydrogencarbonate In water	100%
With sodium tetrahydroborate; sodium hydrogencarbonate In water at 5 - 20℃; for 1.25h;	96.8 mg

: 101567-87-7
(+/-)-8-hydroxy-6-mercapto-octanoic acid

: 17356-08-0
thiourea

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
With hydrogen bromide anschliessend mit wss. Natronlauge;

: 82725-55-1
2-(2-Benzoyloxyethyl)cyclohexanone

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
(i) AcOOH, (ii) thiourea, aq. HI, (iii) aq. KOH; Multistep reaction;

: 27565-41-9
1,4-dithio-D,L-threitol

: 1077-28-7, 62-46-4
Thioctic acid

A: 462-20-4
dihydrolipoic acid

: 16096-98-3, 37031-12-2, 40227-25-6, 74185-01-6, 86023-22-5, 89825-28-5, 14193-38-5
trans-1,2-dithiane-4,5-diol

Conditions

Conditions	Yield
In water-d2 for 48h; Equilibrium constant; phosphate buffer (pD 7.0); also in CD3OD/D2O;

...Expand

: 131760-67-3
N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine

: 1077-28-7, 62-46-4
Thioctic acid

A: 462-20-4
dihydrolipoic acid

B: 131760-68-4
1,2-dimethyl-3,8-dioxo-1,2,5,6-diazadithiocane

Conditions

Conditions	Yield
With buffer (pH 7.0, 2 mM EDTA, 0.1 M phosphate) Equilibrium constant;

...Expand

: 60-24-2
2-hydroxyethanethiol

: 1077-28-7, 62-46-4
Thioctic acid

A: 462-20-4
dihydrolipoic acid

B: 1892-29-1
bis(2-hydroxyethyl) disulfide

Conditions

Conditions	Yield
In water-d2 for 48h; Equilibrium constant; phosphate buffer (pD 7.0); also in CD3OD/D2O;

...Expand

: 6,8-bis-carbamimidoylsulfanyl-octanoic acid; compound with GENERIC INORGANIC NEUTRAL COMPONENT

A: 462-20-4
dihydrolipoic acid

B: 1077-28-7, 62-46-4
Thioctic acid

C: 5,8-Dimercaptooctanoic acid

Conditions

Conditions	Yield
With potassium hydroxide; water for 3h; Hydrolysis; Rearrangement; Cyclization; Heating; Title compound not separated from byproducts;

...Expand

(+-)-6,8-bis-benzylsulfanyl-octanoic acid: (+-)-6,8-bis-benzylsulfanyl-octanoic acid

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
With phosphoric acid
With ammonia; sodium; toluene

(+-)-8-acetylsulfanyl-6-hydroxy-octanoic acid ethyl ester: (+-)-8-acetylsulfanyl-6-hydroxy-octanoic acid ethyl ester

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
With sodium hydroxide beim Erhitzen des Reaktionsprodukts mit Thioharnstoff und wss. Jodwasserstoffsaeure und anschliessend Erhitzen mit wss. Natronlauge;
With sodium hydroxide beim Erhitzen des Reaktionsprodukts mit Thioharnstoff und wss. Jodwasserstoffsaeure und anschliessend Erhitzen mit wss. Natronlauge;

: 17356-08-0
thiourea

(+-)-6,8-dihydroxy-octanoic acid methyl ester: (+-)-6,8-dihydroxy-octanoic acid methyl ester

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
With hydrogen iodide beim Erhitzen des Reaktiosgemisches mit wss. Kalilauge unter Stickstoff;

: 17356-08-0
thiourea

(+-)-8-acetoxy-6-hydroxy-octanoic acid lactone: (+-)-8-acetoxy-6-hydroxy-octanoic acid lactone

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
With hydrogen iodide beim Erhitzen des Reaktiosgemisches mit wss. Kalilauge unter Stickstoff;

: 156594-99-9
8-Ethoxy-6-formyloxyoctanoic acid

A: 462-20-4
dihydrolipoic acid

B (PhAsO)n: (PhAsO)n

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HBr; H2O / 20 h / 116 °C 2: KOH; H2O / 3 h / Heating View Scheme
Multi-step reaction with 3 steps 1: HBr; H2O / 20 h / 116 °C 2: KOH; H2O / 3 h / Heating 3: NaBH4; NaHCO3 / H2O / 0.5 h / 5 °C View Scheme
Multi-step reaction with 3 steps 1.1: HBr; H2O / 20 h / 116 °C 2.1: KOH; H2O / 3 h / Heating 2.2: FeCl3; air / H2O / 2.5 h / pH 8.8 - 11.5 3.1: NaBH4; NaHCO3 / H2O / 0.5 h / 5 °C View Scheme

: 6,8-bis-carbamimidoylsulfanyl-octanoic acid; compound with GENERIC INORGANIC NEUTRAL COMPONENT

A: 462-20-4
dihydrolipoic acid

B (PhAsO)n: (PhAsO)n

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH; H2O / 3 h / Heating 2: NaBH4; NaHCO3 / H2O / 0.5 h / 5 °C View Scheme
Multi-step reaction with 2 steps 1.1: KOH; H2O / 3 h / Heating 1.2: FeCl3; air / H2O / 2.5 h / pH 8.8 - 11.5 2.1: NaBH4; NaHCO3 / H2O / 0.5 h / 5 °C View Scheme

: 104665-85-2
(+/-)-3-acetylsulfanyl-octanedioic acid-8-ethyl ester-1-chloride

: 462-20-4
dihydrolipoic acid

Conditions

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

: 1077-28-7, 62-46-4
Thioctic acid

: 66612-29-1
6-[N-(4-Aminobutyl)-N-ethylamino]-2,3-dihydrophthalazine-1,4-dione

A: 462-20-4
dihydrolipoic acid

B: C14H20N2O4

Conditions

Conditions	Yield
With sodium hydroxide In ethanol

...Expand

: 1070-64-0
6,8-dichlorooctanoic acid ethyl ester

: 462-20-4
dihydrolipoic acid

Conditions

Conditions	Yield
Stage #1: 6,8-dichlorooctanoic acid ethyl ester With sodium sulfide; hydrogen sulfide In ethanol; water under 2625.26 Torr; for 3.41667h; Large scale; Stage #2: With sodium tetrahydroborate; water; sodium hydroxide In ethanol at 70℃; for 2.5h; Pressure; Temperature; Time; Reagent/catalyst; Large scale;

: 462-20-4
dihydrolipoic acid

: 135-02-4
ortho-anisaldehyde

: 5-(2-(2-methoxyphenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%
Stage #1: dihydrolipoic acid; ortho-anisaldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -25 - 20℃; Inert atmosphere;

: 462-20-4
dihydrolipoic acid

: 591-31-1
3-methoxy-benzaldehyde

: 5-(2-(3-methoxyphenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

: 462-20-4
dihydrolipoic acid

: 454-89-7
3-Trifluoromethylbenzaldehyde

: 5-(2-(3-(trifluoromethyl)phenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	99.4%
Stage #1: dihydrolipoic acid; 3-Trifluoromethylbenzaldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -25 - 20℃; Inert atmosphere;

: 462-20-4
dihydrolipoic acid

: 447-61-0
2-Trifluoromethylbenzaldehyde

: 5-(2-(2-(trifluoromethyl)phenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	99.4%

: 462-20-4
dihydrolipoic acid

: 552-89-6
2-nitro-benzaldehyde

: 5-(2-(2-nitrophenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	97.6%

: 67-56-1
methanol

: bismuth(III) chloride

: 462-20-4
dihydrolipoic acid

: 1600506-20-4
methyl 5-(2-chloro-1,3,2-dithiabisman-4-yl)pentanoate

Conditions

Conditions	Yield
at 20℃; for 2h; Inert atmosphere; Darkness;	96%

...Expand

: 462-20-4
dihydrolipoic acid

: 2926-29-6
Langlois reagent

: C9H15F3O2S2

Conditions

Conditions	Yield
With iodine pentoxide In dimethyl sulfoxide at 110℃; for 24h; chemoselective reaction;	94%

: 462-20-4
dihydrolipoic acid

: 587-04-2
3-Chlorobenzaldehyde

: 5-(2-(3-chlorophenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	93.8%

: 462-20-4
dihydrolipoic acid

: 89-98-5
2-chloro-benzaldehyde

: C15H19ClO2S2

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	93.1%
Stage #1: dihydrolipoic acid; 2-chloro-benzaldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -25 - 20℃; Inert atmosphere;

: 462-20-4
dihydrolipoic acid

: 67-64-1
acetone

: 2036-55-7
5-(2,2-dimethyl-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With yttrium(III) trifluoromethanesulfonate In acetonitrile	93%
With boron trifluoride diethyl etherate at 60℃;	75%
With boron trifluoride diethyl etherate at 60℃;	75%

: 462-20-4
dihydrolipoic acid

: 529-20-4
2-methylphenyl aldehyde

: 5-(2-(o-tolyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 45℃; for 12h; Inert atmosphere;	91%
Stage #1: dihydrolipoic acid; 2-methylphenyl aldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -25 - 20℃; Inert atmosphere;

: 462-20-4
dihydrolipoic acid

: 555-16-8
4-nitrobenzaldehdye

: 5-(2-(4-nitrophenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	90.9%

: 462-20-4
dihydrolipoic acid

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 1333319-11-1
trimethylsilyl 6-mercapto-8-(trimethylsilylthio)octanoate

Conditions

Conditions	Yield
With 1H-imidazole at 100℃; for 24h; Inert atmosphere;	90%

: 462-20-4
dihydrolipoic acid

: 1304-76-3
bismuth(III) oxide

: 1600506-19-1
8,6-bis[[4-(4-carboxybutyl)-1,3,2-dithiabisman-2-yl]thio]octanoic acid

Conditions

Conditions	Yield
In methanol at 20℃; for 48h; Darkness;	89%

: 462-20-4
dihydrolipoic acid

: 10025-91-9
antimony(III) chloride

: 1600506-15-7
5-(2-chloro-1,3,2-dithiastibinan-4-yl)pentanoic acid

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 5h;	86%

: 462-20-4
dihydrolipoic acid

: 99-61-6
3-nitro-benzaldehyde

: 5-(2-(3-nitrophenyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	83.9%

: 462-20-4
dihydrolipoic acid

: 104-88-1
4-chlorobenzaldehyde

: 5-(2-(benzo[d][1,3]dioxol-5-yl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 1h; Inert atmosphere;	83.1%

: 67-56-1
methanol

: bismuth (III) nitrate pentahydrate

: 462-20-4
dihydrolipoic acid

A: 46236-19-5
1,2-dithiolane-3-pentanoic acid methyl ester

B: 1600506-22-6
methyl 8,6-bis[[4-(5-methoxy-5-oxopentyl)-1,3,2-dithiabisman-2-yl]thio]octanoate

Conditions

Conditions	Yield
at 20℃; for 5h; Inert atmosphere; Darkness; Overall yield = 175 mg;	A 7 %Spectr. B 81%

...Expand

: 462-20-4
dihydrolipoic acid

: 620-23-5
m-tolyl aldehyde

: 5-(2-(m-tolyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	80.1%

: 462-20-4
dihydrolipoic acid

: 2-nitrophenyl-[76As]-arsonic acid

: 5-[2-(2-nitrophenyl)-1,3,2-dithi-[76As]-arsinan-4-yl]pentanoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water at 40℃; for 1h; Cyclization;	80%

: 462-20-4
dihydrolipoic acid

: (3-bromopropyl)phosphine

: 244007-29-2
6,8-bis-(3-phosphanyl-propylsulfanyl)-octanoic acid

Conditions

Conditions	Yield
Stage #1: dihydrolipoic acid With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Metallation; Stage #2: (3-bromopropyl)phosphine In tetrahydrofuran for 12h; Alkylation; Heating;	80%

: 462-20-4
dihydrolipoic acid

: 104-87-0
4-methyl-benzaldehyde

: 5-(2-(p-tolyl)-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	79%
Stage #1: dihydrolipoic acid; 4-methyl-benzaldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -25 - 20℃; Inert atmosphere;

: 462-20-4
dihydrolipoic acid

: 100-52-7
benzaldehyde

: 107275-54-7
5-(2-phenyl-1,3-dithian-4-yl)pentanoic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;	78%
With polyphosphoric acid trimethylsilyl ester In dichloromethane at 20℃; for 2h;	60%
With hydrogenchloride; zinc(II) chloride

: 67-56-1
methanol

: bismuth (III) nitrate pentahydrate

: 462-20-4
dihydrolipoic acid

: methyl 5-[2-(nitrooxy)-1,3,2-dithiabisman-4-yl]pentanoate

Conditions

Conditions	Yield
for 5h; Inert atmosphere; Darkness;	77%

...Expand

: 462-20-4
dihydrolipoic acid

: 587-85-9
diphenylmercury(II)

: Hg(C6H5Hg)2(SCH2CH2CH(S)(CH2)4C(O)OH)2*C4H8O

Conditions

Conditions	Yield
In tetrahydrofuran (N2), stirred at room temp. for 48 h; concd. (vac), ppt. washed (THF), dried briefly (vac.); elem. anal.;	76%

: 462-20-4
dihydrolipoic acid

: 76-83-5
trityl chloride

: 1161852-24-9
C46H44O2S2

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 3h;	76%

: 462-20-4
dihydrolipoic acid

: 1304-76-3
bismuth(III) oxide

: 1600506-17-9
5,5'-[oxybis(1,3,2-dithiabismane-2,4-diyl)]dipentanoic acid

Conditions

Conditions	Yield
In methanol at 20℃; for 48h; Darkness;	76%

: 67-56-1
methanol

: 462-20-4
dihydrolipoic acid

: methyl 5-[2-(nitrooxy)-1,3,2-dithiabisman-4-yl]pentanoate

A: 46236-19-5
1,2-dithiolane-3-pentanoic acid methyl ester

B: 1600506-22-6
methyl 8,6-bis[[4-(5-methoxy-5-oxopentyl)-1,3,2-dithiabisman-2-yl]thio]octanoate

Conditions

Conditions	Yield
at 20℃; for 24h; Darkness; Overall yield = 149 mg;	A 8 %Spectr. B 72%

...Expand

Octanoic acid, 6,8-dimercapto- Specification

This chemical is called Octanoic acid, 6,8-dimercapto-, and its systematic name is 6,8-disulfanyloctanoic acid. With the molecular formula of C₈H₁₆O₂S₂, its molecular weight is 208.34. The CAS registry number of this chemical is 462-20-4.

Other characteristics of the Octanoic acid, 6,8-dimercapto- can be summarised as followings: (1)ACD/LogP: 2.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.24; (4)ACD/BCF (pH 5.5): 3.252; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 46.926; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 9; (11)Polar Surface Area: 114.9 ?2; (12)Index of Refraction: 1.527; (13)Molar Refractivity: 56.428 cm³; (14)Molar Volume: 183.688 cm³; (15)Polarizability: 22.37×10^-24cm³; (16)Surface Tension: 44.087 dyne/cm; (17)Density: 1.134 g/cm³; (18)Flash Point: 172.027 °C; (19)Enthalpy of Vaporization: 66.631 kJ/mol; (20)Boiling Point: 360.834 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25°C.

Uses of this chemical: The Octanoic acid, 6,8-dimercapto- could react with benzaldehyde, and obtain the 5-(2-phenyl-[1,3]dithian-4-yl)-valeric acid. This reaction needs the reagent of polyphosphoric acid trimethylsilyl ester, and the solvent of CH₂Cl₂. The yield is 60%. In addition, this reaction should be taken for 2 hours at the temperature of 20 °C.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: C(CCC(=O)O)CC(CCS)S
2.InChI: InChI=1/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
3.InChIKey: IZFHEQBZOYJLPK-UHFFFAOYAP

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	100mg/kg (100mg/kg)		National Technical Information Service. Vol. AD277-689,

Product Name

DIHYDROLIPOIC ACID

Synthetic route

Octanoic acid, 6,8-dimercapto- Specification

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