(6R)-6,8-disulfanyloctanoic acid

• ChemBase ID: 3410
• Molecular Formular: C8H16O2S2
• Molecular Mass: 208.34144
• Monoisotopic Mass: 208.05917175
• SMILES: C(=O)(O)CCCC[C@H](CCS)S
• Canonical SMILES: SCC[C@@H](CCCCC(=O)O)S
• InChI: InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)/t7-/m1/s1
• InChIKey: IZFHEQBZOYJLPK-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6,8-disulfanyloctanoic acid
• IUPAC Traditional name: (R)-dihydrolipoic acid
• Synonyms: Dihydrolipoic Acid; R-DHLA; (R)-Dihydro-α-lipoic acid; (R)-6,8-Dimercaptooctanoic acid; (R)-Dihydrolipoic acid; (R)-6,8-二巯基辛酸; (R)-二氢-α-硫辛酸; (R)-二氢硫辛酸

Database IDs

• CAS Number: 119365-69-4; 462-20-4
• MDL Number: MFCD10566606
• Beilstein Number: 1722776
• PubChem SID: 46508127; 160966850
• PubChem CID: 9834298

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.9104905
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 1.5143276
• LogD (pH = 7.4): -0.2517312
• Log P: 2.2028031
• Molar Refractivity: 55.9366 cm^3
• Polarizability: 22.09833 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.24
• LOG S: -3.3
• Solubility (Water): 1.03e-01 g/l

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -11±2°, c = 1 in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C8H16O2S2

DETAILS

DrugBank - DB03760

Drug information: experimental

Sigma Aldrich - 19772

Biochem/physiol Actions
R-DHLA regenerates the antioxidants vitamin C, thioredoxin and glutathione which in turn can recycle vitamin E.