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Octanoic acid, 6,8-dimercapto-

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Name

Octanoic acid, 6,8-dimercapto-

EINECS N/A
CAS No. 462-20-4 Density 1.134 g/cm3
PSA 114.90000 LogP 2.24970
Solubility N/A Melting Point 60ºC
Formula C8H16O2S2 Boiling Point 360.8 °C at 760 mmHg
Molecular Weight 208.346 Flash Point 172 °C
Transport Information N/A Appearance light yellow liquid
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 462-20-4 (DIHYDROLIPOIC ACID) Hazard Symbols IrritantXi
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;

Article Data 63

Octanoic acid, 6,8-dimercapto- Synthetic route

1077-28-7, 62-46-4

Thioctic 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%
1200-22-2

(R)-1,2-dithiolane-3-pentanoic 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
101567-87-7

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

17356-08-0

thiourea

462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
With hydrogen bromide anschliessend mit wss. Natronlauge;
82725-55-1

2-(2-Benzoyloxyethyl)cyclohexanone

462-20-4

dihydrolipoic acid

Conditions
ConditionsYield
(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

Conditions
ConditionsYield
In water-d2 for 48h; Equilibrium constant; phosphate buffer (pD 7.0); also in CD3OD/D2O;
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
ConditionsYield
With buffer (pH 7.0, 2 mM EDTA, 0.1 M phosphate) Equilibrium constant;
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
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

A

462-20-4

dihydrolipoic acid

B

1077-28-7, 62-46-4

Thioctic acid

C

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

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

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;

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,

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