Thioctic Acid
Title: Thioctic Acid
CAS Registry Number: 62-46-4
CAS Name: 1,2-Dithiolane-3-pentanoic acid
Additional Names: 1,2-dithiolane-3-valeric acid; 6,8-thioctic acid; a-lipoic acid; 5-(1,2-dithiolan-3-yl)valeric acid; 5-[3-(1,2-dithiolanyl)]pentanoic acid; d-[3-(1,2-dithiacyclopentyl)]pentanoic acid; protogen A; acetate replacing factor; pyruvate oxidation factor
Trademarks: Biletan (Gador); Thioctacid (Viatris); Thioctan (Katwijk); Tioctan (Fujisawa)
Molecular Formula: C8H14O2S2
Molecular Weight: 206.33
Percent Composition: C 46.57%, H 6.84%, O 15.51%, S 31.08%
Literature References: Growth factor for many bacteria and protozoa; prosthetic group, coenzyme, or substrate in plants, microorganisms, and animal tissues. Isoln of naturally occurring d-form: L. J. Reed et al., Science 114, 93 (1951); eidem, J. Am. Chem. Soc. 75, 1267 (1953); Patterson et al., ibid. 76, 1823 (1954). Syntheses of dl-form: Bullock et al., ibid. 74, 1868, 3455 (1952); Hornberger et al., ibid. 2382; Reed, US 2980716 and US 3049549 (1961, 1962 to Res. Corp.); Lewis, Raphael, J. Chem. Soc. 1962, 4263; Ose et al., US 3223712 (1965 to Yamanouchi); J. Tsuji et al., J. Org. Chem. 43, 3606 (1978). Biosynthesis via linoleic acid: J. P. Carreau Methods Enzymol. 62, 152-158 (1974). Enantioselective synthesis of d-form: P. C. Bulmanpage et al., Chem. Commun. 1986, 1408. Clinical study in treatment of Wilson's disease: S. F. Gomes da Costa, Arzneim.-Forsch. 20, 1210 (1970). Use in treatment of mushroom poisoning: R. Plotzker et al., Am. J. Med. Sci. 283, 79 (1982); J. P. Hanrahan, M. A. Gordon, J. Am. Med. Assoc. 251, 1057 (1984). Reviews: Wagner, Folkers, Vitamins and Coenzymes (Interscience, New York, 1964) pp 244-263; Schmidt et al., Angew. Chem. Int. Ed. 4, 846 (1965); Schmidt et al., Adv. Enzymol. Relat. Areas Mol. Biol. 32, 423 (1969).
 
Derivative Type: Sodium salt
CAS Registry Number: 2319-84-8
Molecular Formula: C8H13NaO2S2
Molecular Weight: 228.31
Percent Composition: C 42.09%, H 5.74%, Na 10.07%, O 14.02%, S 28.09%
Properties: White powder, sol in water. pH of aq solns about 7.4.
 
Derivative Type: d-Form
CAS Registry Number: 1200-22-2
Properties: Crystals by vacuum sublimation (at 85-90° and 25 microns). mp 46-48° (microblock). [a]D23 +104° (c = 0.88 in benzene). uv max (methanol): 333 nm (e 150). pKa 5.4. Practically insol in water. Sol in fat solvents.
Melting point: mp 46-48° (microblock)
pKa: pKa 5.4
Optical Rotation: [a]D23 +104° (c = 0.88 in benzene)
Absorption maximum: uv max (methanol): 333 nm (e 150)
 
Derivative Type: dl-Form
CAS Registry Number: 1077-28-7
Properties: Yellow needles from cyclohexane, mp 60-61°. bp 160-165°. uv spectrum: Calvin, Fed. Proc. 13, 703 (1954). Practically insol in water. Sol in fat solvents. Forms a water-soluble sodium salt.
Melting point: mp 60-61°
Boiling point: bp 160-165°
 
Derivative Type: l-Form
CAS Registry Number: 1077-27-6
Properties: Crystals from cyclohexane, mp 45-47.5° (microblock). [a]D23 -113° (c = 1.88 in benzene). uv max (methanol): 330 nm (e 140).
Melting point: mp 45-47.5° (microblock)
Optical Rotation: [a]D23 -113° (c = 1.88 in benzene)
Absorption maximum: uv max (methanol): 330 nm (e 140)
 
Derivative Type: Ethylenediamine
Trademarks: Tioctidasi (ISI)
 
Therap-Cat: Treatment of liver disease; antidote to poisonous mushrooms (Amanita species).
Keywords: Hepatoprotectant.

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