(R)-dihydrolipoic acid

Base Information

• Chemical Name: (R)-dihydrolipoic acid
• CAS No.: 119365-69-4
• Molecular Formula: C8H16 O2 S2
• Molecular Weight: 208.346
• European Community (EC) Number: 663-883-7
• UNII: 00K1YL9Q69
• DSSTox Substance ID: DTXSID60963521
• Nikkaji Number: J67.184C
• Wikidata: Q27895533
• Metabolomics Workbench ID: 52411
• ChEMBL ID: CHEMBL1235647
• Mol file: 119365-69-4.mol

Synonyms:(R)-dihydrolipoic acid;119365-69-4;Dihydrolipoic acid, R;(R)-6,8-DIMERCAPTOOCTANOIC ACID;Octanoic acid, 6,8-dimercapto-, (6R)-;(6R)-6,8-dimercaptooctanoic acid;Dihydrolipoic acid, (R)-;Dihydrothioctic acid, (R)-;RDHLA;(+)-6,8-Dithiooctanoic acid;(R)-DHLA;(6R)-DHLA;UNII-00K1YL9Q69;(R)-Dihydro-alpha-lipoic acid;(R)-6,8-Dihydrothioctic acid;(R)-6,8-Dimercaptooctanoicacid;CHEBI:45230;(6R)-6,8-dihydrothioctic acid;00K1YL9Q69;(6R)-6,8-disulfanyloctanoic acid;r-dihydrolipoic acid;C8H16O2S2;(R)-dihydrothioctic acid;SCHEMBL867951;CHEMBL1235647;DTXSID60963521;IZFHEQBZOYJLPK-SSDOTTSWSA-N;AKOS015914494;R-DIHYDROLIPOIC ACID [WHO-DD];(6R)-6,8-bis(sulfanyl)octanoic acid;DB03760;(R)-DIHYDRO-.ALPHA.-LIPOIC ACID;C02147;Q27895533

Chemical Property of (R)-dihydrolipoic acid

Chemical Property:

• Boiling Point: 361 ºC
• PKA: 4.74±0.10(Predicted)
• Flash Point: 172 ºC
• PSA: 114.90000
• Density: 1.134
• LogP: 2.24970
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 208.05917210
• Heavy Atom Count: 12
• Complexity: 128

Purity/Quality:

98% ^*data from raw suppliers

(R)-6,8-DimercaptooctanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(=O)O)CC(CCS)S
• Isomeric SMILES: C(CCC(=O)O)C[C@H](CCS)S

Technology Process of (R)-dihydrolipoic acid

There total 24 articles about (R)-dihydrolipoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

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

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

DOI:10.1002/cbdv.201500272

Reference yield:

(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)

Guidance literature:

With sodium borohydrid; In water; toluene;

Reference yield:

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

Guidance literature:

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

With pyridine; potassium hydroxide; sodium tetrahydroborate; ethanol; yeast; water; triethylamine; sodium chloride; In tetrahydrofuran; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; 1: Acylation / 2: Ring cleavage / 3: Reduction / 4: Reduction / 5: Mesylation / 6: Substitution / 7: Hydrolysis;

DOI:10.1515/znb-1999-0514

upstream raw materials:

Thioctic acid

(R)-8-hydroxy-6-mercapto-octanoic acid

thiourea

Methyl (6R)-6,8-diacetyldihydrolipoate

Downstream raw materials:

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

(+)-Lipoic acid

(-)-Lipoic acid

Refernces

• 1、 Nambu, Yoko,Endo, Takeshi. "STEREOSELECTIVE REDUCTION OF RACEMIC N-HYDROXYAMINO ACIDS BY OPTICALLY ACTIVE THIOLS-IRON(II)". . p. 999 - 1002. Retrieved 1985.
• 2、 -. "METHOD FOR PRODUCING DIHYDROLIPOIC ACID AND SALT THEREOF". Paragraph 0017; 0074. . Retrieved 2018/08/09.
• 3、 -. "Shikonin thioctic ester derivatives as well as synthetic method and application thereof". Paragraph 0020. . Retrieved 2017/11/30.