Product Name

  • Name

    (R)-(+)-1,2-Dithiolane-3-pentanoic acid

  • EINECS 638-752-2
  • CAS No. 1200-22-2
  • Article Data52
  • CAS DataBase
  • Density 1.218 g/cm3
  • Solubility
  • Melting Point 48-52 °C(lit.)
  • Formula C8H14O2S2
  • Boiling Point 362.5 °C at 760 mmHg
  • Molecular Weight 206.33
  • Flash Point 173 °C
  • Transport Information
  • Appearance yellow crystalline solid
  • Safety 20-36-26-35
  • Risk Codes 22-36/38
  • Molecular Structure Molecular Structure of 1200-22-2 ((R)-(+)-1,2-Dithiolane-3-pentanoic acid)
  • Hazard Symbols
  • Synonyms 1,2-Dithiolane-3-pentanoicacid, (R)-;1,2-Dithiolane-3-valeric acid, (+)- (8CI);1,2-Dithiolane-3-pentanoicacid, (3R)-;(R)-Lipoic acid;(R)-a-Lipoic acid;Berlition;Byodinoral 300;Lipoec;Lipoic acid;R-(+)-Thioctic acid;Thioderm;Thiogamma;Tiobec;Tiobec Retard;d-Thioctic acid;a-(+)-Lipoic acid;a-Lipoic acid;
  • PSA 87.90000
  • LogP 2.78510

Synthetic route

(S)-6,8-dichlorooctanoic acid ethylester

(S)-6,8-dichlorooctanoic acid ethylester

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

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

Conditions
ConditionsYield
Stage #1: (S)-6,8-dichlorooctanoic acid ethylester With sodium sulfide; sulfur In water at 80℃; for 2h;
Stage #2: With water; sodium hydroxide at 80℃; for 8h; Temperature;		99.8%
With sodium sulfide; sulfur
Stage #1: (S)-6,8-dichlorooctanoic acid ethylester With sodium sulfide; sulfur In water at 82℃; for 4.5h;
Stage #2: With water; sodium hydroxide In toluene at 92℃; for 8h; pH=1; Solvent; Temperature;		n/a
(+)-isopropyl lipoate
97961-65-4

(+)-isopropyl lipoate

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

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

Conditions
ConditionsYield
With water; potassium carbonate In methanol at 22℃; for 40h;96%
(R)-6,8-dichloroctanoic acid
188412-21-7

(R)-6,8-dichloroctanoic acid

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

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

Conditions
ConditionsYield
With sodium sulfide; N-benzyl-N,N,N-triethylammonium chloride; sulfur In water at 85℃; Reagent/catalyst; Temperature;92.1%
C8H14O2S2*C7H9NO

C8H14O2S2*C7H9NO

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

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

Conditions
ConditionsYield
With citric acid In methanol; toluene at 35 - 40℃; for 3h; Temperature; Darkness; Industrial scale;83.1%
[ethyl (5R)-5-(1,2-dithiolan-3yl)pentanoate]
104726-74-1

[ethyl (5R)-5-(1,2-dithiolan-3yl)pentanoate]

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

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

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide In ethanol for 24h; Ambient temperature;75%
With potassium hydroxide In ethanol at 20℃; for 24h;75%
With potassium hydroxide In ethanol at 20℃; for 24h;75%
hydrolysis;
With sodium hydroxide
(+)-6,8-dichlorooctanoic acid

(+)-6,8-dichlorooctanoic acid

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

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

Conditions
ConditionsYield
Product distribution / selectivity;72%
(R)-5-[1,2-dithiolan-3-yl]pentanoic acid methyl ester
99427-00-6

(R)-5-[1,2-dithiolan-3-yl]pentanoic acid methyl ester

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

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

Conditions
ConditionsYield
With potassium hydroxide In methanol for 3h; Ambient temperature;70%
With potassium hydroxide; water for 24h;54%
Stage #1: (R)-5-[1,2-dithiolan-3-yl]pentanoic acid methyl ester With potassium hydroxide In methanol; water at 50℃; for 2h;
Stage #2: With phosphoric acid In methanol; water; toluene at 30℃;		45%
With potassium carbonate In methanol; water
Potassium; (S)-6,8-bis-methanesulfonyloxy-octanoate

Potassium; (S)-6,8-bis-methanesulfonyloxy-octanoate

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

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

Conditions
ConditionsYield
52%
C8H11N*C8H14O2S2

C8H11N*C8H14O2S2

A

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

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

B

(S)-lipoic acid
62-46-4, 1077-27-6, 1077-28-7, 1200-22-2, 52578-51-5

(S)-lipoic acid

Conditions
ConditionsYield
With sulfuric acid In acetone at 15 - 60℃; for 2h; Temperature; Solvent;A 47.5%
B n/a
C8H11N*C8H14O2S2

C8H11N*C8H14O2S2

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

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

Conditions
ConditionsYield
With sulfuric acid In acetone at 15 - 40℃; for 24h; Solvent;46%
(S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid
107554-84-7

(S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid

A

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

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

B

(S)-lipoic acid
62-46-4, 1077-27-6, 1077-28-7, 1200-22-2, 52578-51-5

(S)-lipoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfide; potassium hydroxide In water; N,N-dimethyl-formamide at 80℃; for 28h; Title compound not separated from byproducts;A n/a
B 45%
6,8-dichlorooctanoic acid ethyl ester
1070-64-0

6,8-dichlorooctanoic acid ethyl ester

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

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

Conditions
ConditionsYield
With ammonium hydrogen sulfite; sodium sulfide nonahydrate; sulfur In propan-1-ol; water; isopropyl alcohol at 70℃; for 3.5h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Darkness;30.6%
Thioctic acid
1077-28-7, 62-46-4

Thioctic acid

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

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

Conditions
ConditionsYield
With cinchonidine salt
(R)-6,8-dimercaptooctanoic acid
119365-69-4

(R)-6,8-dimercaptooctanoic acid

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

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

Conditions
ConditionsYield
With iron(III) chloride; potassium carbonate
With chloroform; iodine; potassium iodide
With mushroom tyrosinase
(S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid
107554-84-7

(S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid

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

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

Conditions
ConditionsYield
With sodium sulfide; potassium hydroxide; sulfur 1.) 5 min, 2.) DMF, 80 deg C, 24h; Yield given. Multistep reaction;
(7R,10S)-7-Isopropyl-10-methyl-1,5-dithia-spiro[5.5]undecane
114529-48-5

(7R,10S)-7-Isopropyl-10-methyl-1,5-dithia-spiro[5.5]undecane

A

l-menthone
3391-87-5

l-menthone

B

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

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

Conditions
ConditionsYield
Multistep reaction;
(3S)-6-bromo-1,3-isopropylidendioxyhexane
139685-60-2

(3S)-6-bromo-1,3-isopropylidendioxyhexane

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

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

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

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

A

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

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

B

(S)-lipoic acid
62-46-4, 1077-27-6, 1077-28-7, 1200-22-2, 52578-51-5

(S)-lipoic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol Yield given. Title compound not separated from byproducts;
sodium-salt of/the/ (+)-6,8-dichloro-octanoic acid

sodium-salt of/the/ (+)-6,8-dichloro-octanoic acid

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

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

Conditions
ConditionsYield
With ethanol; sodium disulfide
(6S)-(-)-methyl 6,8-dihydroxyoctanoate
116349-04-3

(6S)-(-)-methyl 6,8-dihydroxyoctanoate

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / CH2Cl2
2: Na2S; sulphur / dimethylformamide / 24 h / 90 °C
3: K2CO3 / methanol; H2O
View Scheme
Multi-step reaction with 4 steps
1: Et3N / CH2Cl2 / 1 h / 0 °C
2: dimethylformamide; cyclohexane / 4 h / 50 °C
3: H2O; KOH / 6 h / 20 °C
4: FeCl3; air; NaOH / H2O / 3 h / pH 9
View Scheme
Multi-step reaction with 3 steps
1: 92 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C
2: 83 percent / Na2S*9H2O, sulfur / dimethylformamide / 2.42 h / 80 °C
3: 70 percent / aq. KOH / methanol / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 98 percent / Et3N
2: 1.) sodium sulphide nonahydrate, sulphur / 1.) DMF, 80 deg C, 1 h, 2.)DMF, 80 deg C, 67 h, then RT, 17 h
3: 54 percent / 0.1M KOH, H2O / 24 h
View Scheme
(S)-6,8-diphenylmethoxyoctanoic acid
116315-78-7

(S)-6,8-diphenylmethoxyoctanoic acid

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

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.75 g / diethyl ether
2: 87 percent / H2 / Pd/C / ethanol / 5 h / 2585.81 Torr
3: Et3N / CH2Cl2
4: Na2S; sulphur / dimethylformamide / 24 h / 90 °C
5: K2CO3 / methanol; H2O
View Scheme
Multi-step reaction with 5 steps
1: 3percent HCl
2: 95 percent / H2 / 5percent palladium on charcoal / methanol / 1551.4 Torr
3: 98 percent / Et3N
4: 1.) sodium sulphide nonahydrate, sulphur / 1.) DMF, 80 deg C, 1 h, 2.)DMF, 80 deg C, 67 h, then RT, 17 h
5: 54 percent / 0.1M KOH, H2O / 24 h
View Scheme
(6S)-(+)-methyl 6,8-bis(methylsulfonyloxy)octanoate
116349-05-4

(6S)-(+)-methyl 6,8-bis(methylsulfonyloxy)octanoate

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Na2S; sulphur / dimethylformamide / 24 h / 90 °C
2: K2CO3 / methanol; H2O
View Scheme
Multi-step reaction with 3 steps
1: dimethylformamide; cyclohexane / 4 h / 50 °C
2: H2O; KOH / 6 h / 20 °C
3: FeCl3; air; NaOH / H2O / 3 h / pH 9
View Scheme
Multi-step reaction with 2 steps
1: 83 percent / Na2S*9H2O, sulfur / dimethylformamide / 2.42 h / 80 °C
2: 70 percent / aq. KOH / methanol / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 1.) sodium sulphide nonahydrate, sulphur / 1.) DMF, 80 deg C, 1 h, 2.)DMF, 80 deg C, 67 h, then RT, 17 h
2: 54 percent / 0.1M KOH, H2O / 24 h
View Scheme
(S)-1-phenylmethoxyoct-7-en-3-ol
116315-75-4

(S)-1-phenylmethoxyoct-7-en-3-ol

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

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

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 85 percent / TBAI; NaH / dimethylformamide / 2 h / 20 °C
2.1: BH3*DMS / tetrahydrofuran / 2 h / 20 °C
2.2: 88 percent / aq. NaOEt; H2O2 / tetrahydrofuran / 2 h / 20 °C
3.1: aq. NaCl2O; NaOCl; TEMPO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.7
4.1: 1.75 g / diethyl ether
5.1: 87 percent / H2 / Pd/C / ethanol / 5 h / 2585.81 Torr
6.1: Et3N / CH2Cl2
7.1: Na2S; sulphur / dimethylformamide / 24 h / 90 °C
8.1: K2CO3 / methanol; H2O
View Scheme
Multi-step reaction with 8 steps
1: 95 percent
2: 89 percent / diisopentylborane / tetrahydrofuran / 0 °C
3: pyridinium dichromate / dimethylformamide / 0 deg C, then RT, 24 h
4: 3percent HCl
5: 95 percent / H2 / 5percent palladium on charcoal / methanol / 1551.4 Torr
6: 98 percent / Et3N
7: 1.) sodium sulphide nonahydrate, sulphur / 1.) DMF, 80 deg C, 1 h, 2.)DMF, 80 deg C, 67 h, then RT, 17 h
8: 54 percent / 0.1M KOH, H2O / 24 h
View Scheme
(S)-6,8-diphenylmethoxyoct-1-ene
116315-76-5

(S)-6,8-diphenylmethoxyoct-1-ene

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

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: BH3*DMS / tetrahydrofuran / 2 h / 20 °C
1.2: 88 percent / aq. NaOEt; H2O2 / tetrahydrofuran / 2 h / 20 °C
2.1: aq. NaCl2O; NaOCl; TEMPO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.7
3.1: 1.75 g / diethyl ether
4.1: 87 percent / H2 / Pd/C / ethanol / 5 h / 2585.81 Torr
5.1: Et3N / CH2Cl2
6.1: Na2S; sulphur / dimethylformamide / 24 h / 90 °C
7.1: K2CO3 / methanol; H2O
View Scheme
Multi-step reaction with 7 steps
1: 89 percent / diisopentylborane / tetrahydrofuran / 0 °C
2: pyridinium dichromate / dimethylformamide / 0 deg C, then RT, 24 h
3: 3percent HCl
4: 95 percent / H2 / 5percent palladium on charcoal / methanol / 1551.4 Torr
5: 98 percent / Et3N
6: 1.) sodium sulphide nonahydrate, sulphur / 1.) DMF, 80 deg C, 1 h, 2.)DMF, 80 deg C, 67 h, then RT, 17 h
7: 54 percent / 0.1M KOH, H2O / 24 h
View Scheme
(S)-6,8-diphenylmethoxyoctan-1-ol
116315-77-6

(S)-6,8-diphenylmethoxyoctan-1-ol

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

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aq. NaCl2O; NaOCl; TEMPO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.7
2: 1.75 g / diethyl ether
3: 87 percent / H2 / Pd/C / ethanol / 5 h / 2585.81 Torr
4: Et3N / CH2Cl2
5: Na2S; sulphur / dimethylformamide / 24 h / 90 °C
6: K2CO3 / methanol; H2O
View Scheme
Multi-step reaction with 6 steps
1: pyridinium dichromate / dimethylformamide / 0 deg C, then RT, 24 h
2: 3percent HCl
3: 95 percent / H2 / 5percent palladium on charcoal / methanol / 1551.4 Torr
4: 98 percent / Et3N
5: 1.) sodium sulphide nonahydrate, sulphur / 1.) DMF, 80 deg C, 1 h, 2.)DMF, 80 deg C, 67 h, then RT, 17 h
6: 54 percent / 0.1M KOH, H2O / 24 h
View Scheme
(S)-methyl 6,8-diphenylmethoxyoctanoate
116315-79-8

(S)-methyl 6,8-diphenylmethoxyoctanoate

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 87 percent / H2 / Pd/C / ethanol / 5 h / 2585.81 Torr
2: Et3N / CH2Cl2
3: Na2S; sulphur / dimethylformamide / 24 h / 90 °C
4: K2CO3 / methanol; H2O
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / H2 / 5percent palladium on charcoal / methanol / 1551.4 Torr
2: 98 percent / Et3N
3: 1.) sodium sulphide nonahydrate, sulphur / 1.) DMF, 80 deg C, 1 h, 2.)DMF, 80 deg C, 67 h, then RT, 17 h
4: 54 percent / 0.1M KOH, H2O / 24 h
View Scheme
ethyl (S)-6,8-dihydroxy octanoate
104726-72-9

ethyl (S)-6,8-dihydroxy octanoate

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / Et3N / CH2Cl2 / 4 h / 0 °C
2: 72 percent / Na2S; S / dimethylformamide / 24 h / 90 °C
3: 75 percent / KOH / ethanol / 24 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: Et3N / CH2Cl2 / 4 h / 0 °C
2: 70 percent / sodium sulfide nonahydrate, sulfur / dimethylformamide / 24 h / 90 °C
3: 75 percent / 1.) 0.1M potassium hydroxide, 2.) 5M HCl / ethanol / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
2: Na2S - S / dimethylformamide / 90 °C
3: hydrolysis
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 4 h / 0 °C
2: sodiumsulfide nonahydrate; sulfur / N,N-dimethyl-formamide / 24 h / 85 - 90 °C
3: potassium hydroxide / ethanol / 24 h / 20 °C
View Scheme
(S)-Ethyl 6,8-Bis(methylsulphonyloxy)octanoate
104726-73-0

(S)-Ethyl 6,8-Bis(methylsulphonyloxy)octanoate

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / Na2S; S / dimethylformamide / 24 h / 90 °C
2: 75 percent / KOH / ethanol / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 70 percent / sodium sulfide nonahydrate, sulfur / dimethylformamide / 24 h / 90 °C
2: 75 percent / 1.) 0.1M potassium hydroxide, 2.) 5M HCl / ethanol / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: Na2S - S / dimethylformamide / 90 °C
2: hydrolysis
View Scheme
Multi-step reaction with 2 steps
1: sodiumsulfide nonahydrate; sulfur / N,N-dimethyl-formamide / 24 h / 85 - 90 °C
2: potassium hydroxide / ethanol / 24 h / 20 °C
View Scheme
(R)-1,2-dithiolane-3-pentanoic acid
1200-22-2

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

(R)-6,8-dimercaptooctanoic acid
119365-69-4

(R)-6,8-dimercaptooctanoic acid

Conditions
ConditionsYield
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
dimethylbiguanide
657-24-9

dimethylbiguanide

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

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

N,N-dimethylimidodicarbonimidic diamide R-(+)-lipoate
959986-37-9

N,N-dimethylimidodicarbonimidic diamide R-(+)-lipoate

Conditions
ConditionsYield
In methanol for 2h; Product distribution / selectivity;100%
In acetonitrile for 0.166667h; Product distribution / selectivity;95%
In acetone for 0.166667 - 0.5h; Product distribution / selectivity;95%
In methanol; acetone for 0.333333h; Product distribution / selectivity;
pyridoxamine
85-87-0

pyridoxamine

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

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

(3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methanaminium (R)-5-( 1,2-dithiolan-3-yl)pentanoate

(3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methanaminium (R)-5-( 1,2-dithiolan-3-yl)pentanoate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h;100%
In ethanol at 20 - 50℃; for 0.5h;68%
(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
Duloxetine
116539-58-3, 116539-59-4, 116539-60-7, 116817-13-1

Duloxetine

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

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

(S)-N-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-aminium (R)-5-(1,2-dithiolan-3-yl)pentanoate

(S)-N-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-aminium (R)-5-(1,2-dithiolan-3-yl)pentanoate

Conditions
ConditionsYield
In tetrahydrofuran for 2h;100%
tropicamide
1508-75-4

tropicamide

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

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

(R)-5-(1,2-dithiolan-3-yl)pentanoic acid N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide

(R)-5-(1,2-dithiolan-3-yl)pentanoic acid N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;100%
tetrahydrozoline
84-22-0

tetrahydrozoline

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

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

(R)-5-(1,2-dithiolan-3-yl)pentanoate 2-(1,2,3,4-tetrahydronaphthalen-1-yl)-4,5-dihydro-1H-imidazol-1-ium

(R)-5-(1,2-dithiolan-3-yl)pentanoate 2-(1,2,3,4-tetrahydronaphthalen-1-yl)-4,5-dihydro-1H-imidazol-1-ium

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;100%
2-amino-2-hydroxymethyl-1,3-propanediol
77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

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

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

R-lipoic acid tromethamine salt

R-lipoic acid tromethamine salt

Conditions
ConditionsYield
With ethyl acetate at 40℃; for 4h;99.64%
(R)-1,2-dithiolane-3-pentanoic acid
1200-22-2

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

magnesium R-(+)-α-lipoate

magnesium R-(+)-α-lipoate

Conditions
ConditionsYield
With dihydro-(+)-lipoic acid; magnesium methanolate In isopropyl alcohol at 15 - 20℃; for 0.35h; Product distribution / selectivity;98.7%
With magnesium hydroxide In ethanol85%
With magnesium methanolate In methanol; isopropyl alcohol Inert atmosphere;
bethanechol chloride
590-63-6

bethanechol chloride

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

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

2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium (R)-5-(1,2-dithiolan-3-yl)pentanoate

2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium (R)-5-(1,2-dithiolan-3-yl)pentanoate

Conditions
ConditionsYield
Stage #1: bethanechol chloride With sodium hydrogencarbonate In methanol at 20℃; for 0.0833333h;
Stage #2: (R)-1,2-dithiolane-3-pentanoic acid In methanol at 20℃; for 16h;		97.6%
3β-hydroxyoleanane-12-en-28-oic acid(6-bromohexyl) ester
1161826-45-4

3β-hydroxyoleanane-12-en-28-oic acid(6-bromohexyl) ester

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

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

[((5-((R)-1,2-dithiolan-3-yl)pentanoyl)oxy)hexyl]-3β-hydroxyolean-12-en-28-oate

[((5-((R)-1,2-dithiolan-3-yl)pentanoyl)oxy)hexyl]-3β-hydroxyolean-12-en-28-oate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;96%
(R)-1,2-dithiolane-3-pentanoic acid
1200-22-2

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

sodium lipoic acid

sodium lipoic acid

Conditions
ConditionsYield
With sodium ethanolate In ethanol95%
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

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

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

R-(+)-LA dimethylethanolamine salt
919507-94-1

R-(+)-LA dimethylethanolamine salt

Conditions
ConditionsYield
In ethanol95%
methanol
67-56-1

methanol

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

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

(R)-5-[1,2-dithiolan-3-yl]pentanoic acid methyl ester
99427-00-6

(R)-5-[1,2-dithiolan-3-yl]pentanoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid at 78.3℃; for 1h; Dean-Stark;95%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 5h;
With thionyl chloride at 0 - 20℃; for 1h;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Cooling with ice;
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

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

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

(R)-perfluorophenyl 5-(1,2-dithiolan-3-yl)pentanoate

(R)-perfluorophenyl 5-(1,2-dithiolan-3-yl)pentanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 19h;95%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide In dichloromethane at 20℃;94%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 0 - 20℃;
Taurine

Taurine

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

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

N-[(R)-1,2-dithiolane-3-pentanoyl]taurine
874111-37-2

N-[(R)-1,2-dithiolane-3-pentanoyl]taurine

Conditions
ConditionsYield
Stage #1: (R)-1,2-dithiolane-3-pentanoic acid With di(succinimido) carbonate; N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 2h; Darkness;
Stage #2: Taurine With water; N-ethyl-N,N-diisopropylamine In acetone		95%
choline bromide
1927-06-6

choline bromide

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

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

R-lipoic acid choline ester bromide

R-lipoic acid choline ester bromide

Conditions
ConditionsYield
With 2,6-dimethylpyridine; 1,1'-carbonyldiimidazole In 1,2-dichloro-ethane at 20℃; for 24h; Cooling with ice; Green chemistry;95%
With 2,6-dimethylpyridine; 1,1'-carbonyldiimidazole In chloroform at 20℃; for 24h; Solvent; Reagent/catalyst; Temperature;85%
(2S,4R)-1-(6-aminohexanoyl)-4-hydroxy-2-(4,4′-dimethoxytrityloxymethyl)pyrrolidine
851912-61-3

(2S,4R)-1-(6-aminohexanoyl)-4-hydroxy-2-(4,4′-dimethoxytrityloxymethyl)pyrrolidine

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

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

(2S,4R)-4-hydroxy-2-(4,4'-dimethoxytrityloxymethyl)-1-(6-(N-(5-((R)-1,2-dithiolan-3-yl)pentanoylamino)hexanoyl))pyrrolidine

(2S,4R)-4-hydroxy-2-(4,4'-dimethoxytrityloxymethyl)-1-(6-(N-(5-((R)-1,2-dithiolan-3-yl)pentanoylamino)hexanoyl))pyrrolidine

Conditions
ConditionsYield
Stage #1: (R)-1,2-dithiolane-3-pentanoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.166667h;
Stage #2: (2S,4R)-1-(6-aminohexanoyl)-4-hydroxy-2-(4,4′-dimethoxytrityloxymethyl)pyrrolidine In N,N-dimethyl-formamide at 25℃; for 1h;		95%
piperazine
110-85-0

piperazine

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

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

piperazine di-(R)-α-lipoate

piperazine di-(R)-α-lipoate

Conditions
ConditionsYield
In acetone at 20℃; for 4h; Product distribution / selectivity; Reflux;94.5%
In acetone at 0 - 15℃; for 3h;92.3%
In acetone at 0 - 15℃; for 3h;92.3%
In acetone at 0 - 15℃; for 3h;92.3%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

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

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

2,5-dioxopyrrolidin-1-yl 5-(1,2-dithiolan-3-yl)pentanoate
1115175-97-7

2,5-dioxopyrrolidin-1-yl 5-(1,2-dithiolan-3-yl)pentanoate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;94%
With dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 4 - 20℃; for 5h;75.8%
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 16h;66%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere;
bromohexyl-3β-hydroxy-urs-12-en-28-oate
1383539-92-1

bromohexyl-3β-hydroxy-urs-12-en-28-oate

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

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

[((5-((R)-1,2-dithiolan-3-yl)pentanoyl)oxy)hexyl]-3β-hydroxyurs-12-en-28-oate

[((5-((R)-1,2-dithiolan-3-yl)pentanoyl)oxy)hexyl]-3β-hydroxyurs-12-en-28-oate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Solvent; Reagent/catalyst;94%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;94%
3β-hydroxyoleanane-12-en-28-oicacid(4-bromobutyl) ester

3β-hydroxyoleanane-12-en-28-oicacid(4-bromobutyl) ester

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

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

[((5-((R)-1,2-dithiolan-3-yl)pentanoyl)oxy)butyl]-3β-hydroxyolean-12-en-28-oate

[((5-((R)-1,2-dithiolan-3-yl)pentanoyl)oxy)butyl]-3β-hydroxyolean-12-en-28-oate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;94%
2,2,2-tris(hydroxymethyl)ethylamine
7332-39-0

2,2,2-tris(hydroxymethyl)ethylamine

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

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

trometamol (R)-α-lipoate

trometamol (R)-α-lipoate

Conditions
ConditionsYield
In ethanol at 0 - 60℃; Product distribution / selectivity;93.1%
choline chloride
67-48-1

choline chloride

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

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

R-lipoic acid choline ester chloride

R-lipoic acid choline ester chloride

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene at 35℃; for 18h; Cooling with ice; Green chemistry;93%
With dmap; dicyclohexyl-carbodiimide In chloroform at 35℃; for 18h; Solvent; Reagent/catalyst; Temperature;89%
(E)-15,19-dimethyl-3,6,9,12-tetraoxaicosa-14,18-dien-1-ol

(E)-15,19-dimethyl-3,6,9,12-tetraoxaicosa-14,18-dien-1-ol

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

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

C26H46O6S2

C26H46O6S2

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 30℃; for 10h;92.1%
(R)-1,2-dithiolane-3-pentanoic acid
1200-22-2

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

2-chloro-ethanol
107-07-3

2-chloro-ethanol

(R)-lipoic acid 2-chloroethyl ester

(R)-lipoic acid 2-chloroethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 35℃; for 18h; Cooling with ice;92%
L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

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

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

R(+)-lipoic acid L-lysine salt

R(+)-lipoic acid L-lysine salt

Conditions
ConditionsYield
Stage #1: (R)-1,2-dithiolane-3-pentanoic acid With sodium ethanolate In ethanol at 20℃;
Stage #2: L-Lysine hydrochloride In acetone at 55 - 60℃; for 2h; Concentration; Temperature;		92%

R-(+)-alpha-Lipoic acid Chemical Properties

IUPAC Name: 5-[(3R)-Dithiolan-3-yl]pentanoic acid 
Following is the structure of R-(+)-alpha-Lipoic acid (CAS NO.1200-22-2):
                         
Empirical Formula: C8H14O2S2
Molecular Weight: 206.3256
Index of Refraction: 1.562
Molar Refractivity: 54.94 cm3
Molar Volume: 169.3 cm3
Density: 1.218 g/cm3
Flash Point: 173 °C
Melting point 46-49 °C 
Surface Tension: 52.7 dyne/cm
Appearance: Yellow Crystalline Solid
Enthalpy of Vaporization: 66.83 kJ/mol
Boiling Point: 362.5 °C at 760 mmHg
Vapour Pressure of R-(+)-alpha-Lipoic acid (CAS NO.1200-22-2): 3.07E-06 mmHg at 25 °C
Product Categoriesof R-(+)-alpha-Lipoic acid (CAS NO.1200-22-2): FINE Chemical & INTERMEDIATES; Chiral Reagents; Heterocycles; Sulfur & Selenium Compounds; Chiral Building Blocks; Heterocyclic Building Blocks; Others
Canonical SMILES: C1CSSC1CCCCC(=O)O
Isomeric SMILES: C1CSS[C@@H]1CCCCC(=O)O
InChI: 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

R-(+)-alpha-Lipoic acid Uses

 R-(+)-alpha-Lipoic acid (CAS NO.1200-22-2) can be used as a fat-metabolism stimulator .

R-(+)-alpha-Lipoic acid Specification

 R-(+)-alpha-Lipoic acid , its cas register number 1200-22-2. It also can be called R-(+)-alpha-Lipoic acid ; and (R)-(+)-1,2-Dithiolane-3-pentanoic acid .

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