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462-20-4

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462-20-4 Usage

Uses

γ-Lipoic Acid, is a metabolite of α-Lipoic Acid (L468730), which is a over-the-counter nutritional supplements, that has been used as antioxidant. It is also fat-metabolism stimulator, and thus used a "weight loss" and "energy" supplement.

Definition

ChEBI: A thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.

Check Digit Verification of cas no

The CAS Registry Mumber 462-20-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 2 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 462-20:
(5*4)+(4*6)+(3*2)+(2*2)+(1*0)=54
54 % 10 = 4
So 462-20-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)

462-20-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (D4586)  Dihydrolipoic Acid  >97.0%(GC)(T)

  • 462-20-4

  • 200mg

  • 880.00CNY

  • Detail
  • TCI America

  • (D4586)  Dihydrolipoic Acid  >97.0%(GC)(T)

  • 462-20-4

  • 1g

  • 2,750.00CNY

  • Detail
  • Sigma-Aldrich

  • (T8260)  Lipoicacid,reduced  analytical standard

  • 462-20-4

  • T8260-25MG

  • 400.14CNY

  • Detail
  • Sigma-Aldrich

  • (T8260)  Lipoicacid,reduced  analytical standard

  • 462-20-4

  • T8260-100MG

  • 1,010.88CNY

  • Detail
  • Sigma-Aldrich

  • (T8260)  Lipoicacid,reduced  analytical standard

  • 462-20-4

  • T8260-1G

  • 5,544.63CNY

  • Detail

462-20-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name dihydrolipoic acid

1.2 Other means of identification

Product number -
Other names Gamma-Lipoic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:462-20-4 SDS

462-20-4Synthetic route

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

Thioctic acid

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
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%
(R)-1,2-dithiolane-3-pentanoic acid
1200-22-2

(R)-1,2-dithiolane-3-pentanoic acid

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid; sodium hydrogencarbonate In water100%
With sodium tetrahydroborate; sodium hydrogencarbonate In water at 5 - 20℃; for 1.25h;96.8 mg
(+/-)-8-hydroxy-6-mercapto-octanoic acid
101567-87-7

(+/-)-8-hydroxy-6-mercapto-octanoic acid

thiourea
17356-08-0

thiourea

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
With hydrogen bromide anschliessend mit wss. Natronlauge;
2-(2-Benzoyloxyethyl)cyclohexanone
82725-55-1

2-(2-Benzoyloxyethyl)cyclohexanone

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
(i) AcOOH, (ii) thiourea, aq. HI, (iii) aq. KOH; Multistep reaction;
1,4-dithio-D,L-threitol
27565-41-9

1,4-dithio-D,L-threitol

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

Thioctic acid

A

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
In water-d2 for 48h; Equilibrium constant; phosphate buffer (pD 7.0); also in CD3OD/D2O;
N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine
131760-67-3

N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine

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

Thioctic acid

A

dihydrolipoic acid
462-20-4

dihydrolipoic acid

B

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

1,2-dimethyl-3,8-dioxo-1,2,5,6-diazadithiocane

Conditions
ConditionsYield
With buffer (pH 7.0, 2 mM EDTA, 0.1 M phosphate) Equilibrium constant;
2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

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

Thioctic acid

A

dihydrolipoic acid
462-20-4

dihydrolipoic acid

B

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

bis(2-hydroxyethyl) disulfide

Conditions
ConditionsYield
In water-d2 for 48h; Equilibrium constant; phosphate buffer (pD 7.0); also in CD3OD/D2O;
6,8-bis-carbamimidoylsulfanyl-octanoic acid; compound with GENERIC INORGANIC NEUTRAL COMPONENT

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

A

dihydrolipoic acid
462-20-4

dihydrolipoic acid

B

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

Thioctic acid

C

5,8-Dimercaptooctanoic acid

5,8-Dimercaptooctanoic acid

Conditions
ConditionsYield
With potassium hydroxide; water for 3h; Hydrolysis; Rearrangement; Cyclization; Heating; Title compound not separated from byproducts;
(+-)-6,8-bis-benzylsulfanyl-octanoic acid

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

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
With phosphoric acid
With ammonia; sodium; toluene
(+-)-8-acetylsulfanyl-6-hydroxy-octanoic acid ethyl ester

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

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
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;
thiourea
17356-08-0

thiourea

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

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

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
With hydrogen iodide beim Erhitzen des Reaktiosgemisches mit wss. Kalilauge unter Stickstoff;
thiourea
17356-08-0

thiourea

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

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

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
With hydrogen iodide beim Erhitzen des Reaktiosgemisches mit wss. Kalilauge unter Stickstoff;
8-Ethoxy-6-formyloxyoctanoic acid
156594-99-9

8-Ethoxy-6-formyloxyoctanoic acid

A

dihydrolipoic acid
462-20-4

dihydrolipoic acid

B

(PhAsO)n

(PhAsO)n

Conditions
ConditionsYield
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

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

A

dihydrolipoic acid
462-20-4

dihydrolipoic acid

B

(PhAsO)n

(PhAsO)n

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

(+/-)-3-acetylsulfanyl-octanedioic acid-8-ethyl ester-1-chloride

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
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
Thioctic acid
1077-28-7, 62-46-4

Thioctic acid

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

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

A

dihydrolipoic acid
462-20-4

dihydrolipoic acid

B

C14H20N2O4

C14H20N2O4

Conditions
ConditionsYield
With sodium hydroxide In ethanol
6,8-dichlorooctanoic acid ethyl ester
1070-64-0

6,8-dichlorooctanoic acid ethyl ester

dihydrolipoic acid
462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
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;
dihydrolipoic acid
462-20-4

dihydrolipoic acid

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

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

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

Conditions
ConditionsYield
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;
dihydrolipoic acid
462-20-4

dihydrolipoic acid

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;100%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

3-Trifluoromethylbenzaldehyde
454-89-7

3-Trifluoromethylbenzaldehyde

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

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

Conditions
ConditionsYield
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;
dihydrolipoic acid
462-20-4

dihydrolipoic acid

2-Trifluoromethylbenzaldehyde
447-61-0

2-Trifluoromethylbenzaldehyde

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;99.4%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;97.6%
methanol
67-56-1

methanol

bismuth(III) chloride

bismuth(III) chloride

dihydrolipoic acid
462-20-4

dihydrolipoic acid

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

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

Conditions
ConditionsYield
at 20℃; for 2h; Inert atmosphere; Darkness;96%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

Langlois reagent
2926-29-6

Langlois reagent

C9H15F3O2S2

C9H15F3O2S2

Conditions
ConditionsYield
With iodine pentoxide In dimethyl sulfoxide at 110℃; for 24h; chemoselective reaction;94%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;93.8%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

C15H19ClO2S2

C15H19ClO2S2

Conditions
ConditionsYield
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;
dihydrolipoic acid
462-20-4

dihydrolipoic acid

acetone
67-64-1

acetone

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

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

Conditions
ConditionsYield
With yttrium(III) trifluoromethanesulfonate In acetonitrile93%
With boron trifluoride diethyl etherate at 60℃;75%
With boron trifluoride diethyl etherate at 60℃;75%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

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

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

Conditions
ConditionsYield
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;
dihydrolipoic acid
462-20-4

dihydrolipoic acid

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;90.9%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

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

1,1,1,3,3,3-hexamethyl-disilazane

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

trimethylsilyl 6-mercapto-8-(trimethylsilylthio)octanoate

Conditions
ConditionsYield
With 1H-imidazole at 100℃; for 24h; Inert atmosphere;90%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

bismuth(III) oxide
1304-76-3

bismuth(III) oxide

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

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

Conditions
ConditionsYield
In methanol at 20℃; for 48h; Darkness;89%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

antimony(III) chloride
10025-91-9

antimony(III) chloride

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

5-(2-chloro-1,3,2-dithiastibinan-4-yl)pentanoic acid

Conditions
ConditionsYield
In acetonitrile at 20℃; for 5h;86%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;83.9%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 1h; Inert atmosphere;83.1%
methanol
67-56-1

methanol

bismuth (III) nitrate pentahydrate

bismuth (III) nitrate pentahydrate

dihydrolipoic acid
462-20-4

dihydrolipoic acid

A

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

1,2-dithiolane-3-pentanoic acid methyl ester

B

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

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

Conditions
ConditionsYield
at 20℃; for 5h; Inert atmosphere; Darkness; Overall yield = 175 mg;A 7 %Spectr.
B 81%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere;80.1%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

2-nitrophenyl-[76As]-arsonic acid

2-nitrophenyl-[76As]-arsonic acid

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

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

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; water at 40℃; for 1h; Cyclization;80%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

(3-bromopropyl)phosphine

(3-bromopropyl)phosphine

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

6,8-bis-(3-phosphanyl-propylsulfanyl)-octanoic acid

Conditions
ConditionsYield
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%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

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

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

Conditions
ConditionsYield
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;
dihydrolipoic acid
462-20-4

dihydrolipoic acid

benzaldehyde
100-52-7

benzaldehyde

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

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

Conditions
ConditionsYield
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
methanol
67-56-1

methanol

bismuth (III) nitrate pentahydrate

bismuth (III) nitrate pentahydrate

dihydrolipoic acid
462-20-4

dihydrolipoic acid

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

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

Conditions
ConditionsYield
for 5h; Inert atmosphere; Darkness;77%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

diphenylmercury(II)
587-85-9

diphenylmercury(II)

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

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

Conditions
ConditionsYield
In tetrahydrofuran (N2), stirred at room temp. for 48 h; concd. (vac), ppt. washed (THF), dried briefly (vac.); elem. anal.;76%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

trityl chloride
76-83-5

trityl chloride

C46H44O2S2
1161852-24-9

C46H44O2S2

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 3h;76%
dihydrolipoic acid
462-20-4

dihydrolipoic acid

bismuth(III) oxide
1304-76-3

bismuth(III) oxide

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

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

Conditions
ConditionsYield
In methanol at 20℃; for 48h; Darkness;76%
methanol
67-56-1

methanol

dihydrolipoic acid
462-20-4

dihydrolipoic acid

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

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

A

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

1,2-dithiolane-3-pentanoic acid methyl ester

B

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

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

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

462-20-4Relevant articles and documents

Design and development of the first peptide-chelating bisphosphane bioconjugate from a novel functionalized phosphorus(III) hydride synthon

Gali, Hariprasad,Karra, Srinivasa R.,Reddy, V. Sreenivasa,Katti, Kattesh V.

, p. 2020 - 2023 (1999)

Remarkable oxidative stability is shown by the carboxylate- functionalized primary bisphosphane 1. Compound 1 can be used in conjugation reactions with biomolecules for functionalization through the COOH group without prior protection of PH2 groups. A novel water-soluble bisphosphane was obtained by reaction of the PH2 groups of 1 with formaldehyde under mild conditions.

Metal ion induced fluorescence resonance energy transfer between crown ether functionalized quantum dots and rhodamine B: Selectivity of K+ ion

Lee, Hsin-Lung,Dhenadhayalan, Namasivayam,Lin, King-Chuen

, p. 4926 - 4933 (2015)

We report a ratiometric fluorescent metal ion sensor based on the mechanism of fluorescence resonance energy transfer (FRET) between synthesized 15-crown-5-ether capped CdSe/ZnS quantum dots (QDCE) and 15-crown-5-ether attached rhodamine B (RBCE) in pH 8.3 buffer solution. Fluorescence titration with different metal ions in pH 8.3 buffer solution of the QDCE-RBCE conjugate showed a decrease and an increase in the fluorescence intensity for QDCE and RBCE moieties respectively due to FRET from QDCE to RBCE. This sensor system shows excellent selectivity towards K+ ions resulting in increasing efficiency of FRET. Energy transfer efficiency depends on the affinity between metal ions and crown ether functionalized with QDCE/RBCE. The detailed analysis of FRET was explored. This water soluble ratiometric sensor system can act as a good FRET probe for sensing applications especially in biological systems.

Design and characterization of α-lipoic acyl shikonin ester twin drugs as tubulin and PDK1 dual inhibitors

Lin, Hong-Yan,Han, Hong-Wei,Sun, Wen-Xue,Yang, Yu-Shun,Tang, Cheng-Yi,Lu, Gui-Hua,Qi, Jin-Liang,Wang, Xiao-Ming,Yang, Yong-Hua

, p. 137 - 150 (2018)

Shikonin exhibits powerful anticancer activities for various cancer cells, but its poor solubility and strong toxicity hinder its development as clinical anticancer agent. We previously confirmed that shikonin and its derivatives can disturb mitosis through targeting tubulin. In this study, α-lipoic acid, the naturally-occurring co-factor of pyruvate dehydrogenase (PDH), was introduced into shikonin to design the twin drugs against both mitosis (tubulin) and glycolysis (PDK). 18 kinds of α-lipoic acid shikonin ester derivatives were achieved through three rounds of screening process performed by computer assistant drug design method, being designated as the outstanding compounds. Among them, 1c displayed the most potent cytotoxicity towards cervical cancer cells (HeLa) with an IC50 value of 3.14 ± 0.58 μM and inhibited xenotransplanted tumor growth in a dose-dependent manner. Further pharmacologic study demonstrated that 1c can cause cell cycle arrest in G2/M phase as tubulin polymerization inhibitor. Moreover, it also showed good PDK1 inhibitory activity, promoting PDH activity and forced HeLa cells to process more aerobic metabolism to undergo cell apoptosis. We reported here the first dual inhibitors of tubulin and PDK1 based on shikonin. It may form a basis for shikonin optimization through twin drug design framework for the discovery of new and potent shikonin derivatives in the study of targeted cancer therapy.

Facile synthesis of water-soluble fluorescent silver nanoclusters and HgII sensing

Adhikari, Bimalendu,Banerjee, Arindam

, p. 4364 - 4371 (2010)

A single step facile synthesis of highly emissive, water-soluble, fluorescent Ag nanoclusters has been reported using a small molecule, dihydrolipoic acid. These clusters were characterized using ultraviolet/visible (UV/vis) spectroscopy, photoluminescence spectroscopy, Fourier transform infrared spectroscopy (FT-IR), high-resolution transmission electron microscopy (HR-TEM), dynamic light scattering (DLS), and X-ray diffraction (XRD) studies. Mass spectrometric analysis shows the presence of a few atoms in nanoclusters containing only Ag4 and Ag5. The reported fluorescent Ag nanoclusters show excellent optical properties, including narrow emission profile, larger Stokes shift (more than 200 nm), and good photostability. Interestingly, these nanoclusters also exhibit semiconducting property. Moreover, as-prepared fluorescent Ag nanoclusters have been utilized as an indicator for selective and ultrasensitive detection of highly toxic Hg II ions in water, even at subnanomolar concentrations.

Highly chemiluminescent gold nanopopcorns functionalized by N-(aminobutyl)-N-(ethylisoluminol) with lipoic acid as a co-stabilizing reagent

Zhang, Hongli,Liu, Mengxiao,Huang, Guangming,Yu, Yuqi,Shen, Wen,Cui, Hua

, p. 970 - 977 (2013)

Herein we report a novel facile synthesis of Au nanopopcorns (AuNPCs) with high chemiluminescent yield by reducing (±)-α-lipoic acid (LA) and HAuCl4 with N-(aminobutyl)-N-(ethylisoluminol) (ABEI) in ethyl alcohol solution at room temperature through a seed growth method. The morphologies of AuNPCs could be changed by adjusting the mole ratios of ABEI, LA and HAuCl4. The characterization results demonstrated that ABEI and the reduction product of LA as stabilizers were coated on the surface of AuNPCs during the synthesis. The AuNPCs, functionalized with ABEI, could react with various oxidants (H2O2, KMnO4, NaClO, Fe(CN)63- and AgNO3) to produce chemiluminescence (CL). The special morphology of AuNPCs maintains the large specific surface area, inherited from its shape and demonstrated excellent catalytic property when involved in CL reaction with H2O2. Thus the CL efficiency of AuNPCs was more than two orders of magnitude higher than that of ABEI functionalized gold nanoparticles in our previous work. The AuNPCs are capable of direct conjugation with protein and DNA while maintaining their luminescent properties, thus they could be potentially useful as a bio-probe for immunoassays and DNA assays. The Royal Society of Chemistry 2013.

NOVEL LIPOIC ACID-HETEROCYCLE THIOACETAL COMPOUNDS AND USES OF THE SAME

-

Paragraph 0107-0110, (2021/05/04)

The present invention relates to a novel lipoic acid - heterocycle thioacetal compound which converts a lipoic acid having an unstable disulfide structure into a thioacetal, and to the use thereof. The present invention relates to a pharmaceutical composition comprising a lipoic acid - heterocyclic thioacetal compound for preventing or treating degenerative diseases and a health supplement food composition for preventing or alleviating a degenerative disease.

Preparation method of lipoic acid impurity A

-

, (2021/08/11)

The invention relates to a preparation method of a lipoic acid impurity A, and belongs to the field of compound synthesis. The invention aims to overcome the defects of complex operation and harsh reaction conditions in the prior art, and provides the preparation method of the lipoic acid impurity A. The preparation method is mild in condition and high in product purity. The preparation method comprises the following steps: (1) dissolving lipoic acid in a reaction solvent, adding an oxidant for reaction, and removing solids and the solvent after the reaction is completed to obtain a compound B; (2) respectively adding the compound B, sodium thiosulfate and a catalyst into water, then adding hydrochloric acid, carrying out hydrolysis ring-opening reaction, and filtering after the reaction is completed to obtain a compound C; and (3) respectively adding the compound C, sodium sulfide and formaldehyde into the reaction solvent for reaction, extracting after the reaction is completed, drying, and purifying to obtain a compound D lipoic acid impurity A. The method is mild in condition, and the prepared lipoic acid impurity A is high in purity.

PROCESS FOR THE PRODUCTION OF DIHYDROLIPOIC ACID

-

Paragraph 0058, (2019/09/20)

The present invention relates to a multi-step process for the production of dihydrolipoic acid, which can particularly be carried out as a one-pot reaction and without isolation of intermediates.

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