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Substance Name: Thioctic acid [INN:BAN:JAN]
RN: 1077-28-7
UNII: 73Y7P0K73Y
InChIKey: AGBQKNBQESQNJD-UHFFFAOYSA-N

Notes

  • An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase ( KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.
  • An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.

Molecular Formula

  • C8-H14-O2-S2

Molecular Weight

  • 206.329
 

Classification Codes

  • Antioxidants
  • Growth Substances
  • Micronutrients
  • Protective Agents
  • Vitamin B Complex
  • Vitamins
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Names and Synonyms

Name of Substance

  • alpha-Lipoic acid
  • Lipoic acid, alpha [NF]
  • Thioctic Acid
  • Thioctic acid [INN:BAN:JAN]

MeSH Heading

  • Thioctic Acid

Synonyms

  • (+-)-1,2-Dithiolane-3-pentanoic acid
  • (+-)-alpha-Lipoic acid
  • (+-)-Lipoic acid
  • (+-)-Thioctic acid
  • (RS)-alpha-Lipoic acid
  • (RS)-Lipoic acid
  • 1,2-Dithiolane-3-pentanoic acid
  • 1,2-Dithiolane-3-valeric acid
  • 5-(1,2-Dithiolan-3-yl)pentanoic acid
  • 5-(1,2-Dithiolan-3-yl)valeric acid
  • 5-19-07-00237 (Beilstein Handbook Reference)
  • 6,8-Dithiooctanoic acid
  • 6,8-Thioctic acid
  • 6-Thioctic acid
  • Acetate-replacing factor
  • Alipure
  • alpha-lipon 300
  • alpha-Liponic acid
  • alpha-Liponsaeure
  • alpha-Liponsaeure [German]
  • Biletan
  • BRN 0081853
  • BRN 0122410
  • DL-1,2-Dithiolan-3-valeriansaeure
  • DL-1,2-Dithiolan-3-valeriansaeure [German]
  • DL-1,2-Dithiolane 3-valeric acid
  • DL-1,2-Dithiolane-3-valeric acid
  • DL-6,8-Thioctic acid
  • DL-6-Thioctic acid
  • DL-alpha-Lipoic acid
  • dl-Lipoic acid
  • dl-Thioctic acid
  • EINECS 200-534-6
  • EINECS 214-071-2
  • Espa-lipon
  • HSDB 7818
  • Lipoic acid, alpha
  • Liposan
  • Lipothion
  • NSC 628502
  • NSC 90788
  • Protogen A
  • Pyruvate oxidation factor
  • Rac-lipoate
  • Thioctacid
  • Thioctic Acid
  • Thioctic acid dl-form
  • Thioctsan
  • Thioktsaeure
  • Thioktsaeure [German]
  • Thiotacid
  • Tioctacid
  • Tioctidasi
  • Tioctidasi acetate replacing factor
  • UNII-73Y7P0K73Y

Systematic Names

  • 1,2-Dithiolane-3-pentanoic acid, (+-)-
  • 1,2-Dithiolane-3-valeric acid, (+-)-
  • 5-(Dithiolan-3-yl)valeric acid

Registry Numbers

CAS Registry Number

  • 1077-28-7

FDA UNII

  • 73Y7P0K73Y

Other Registry Numbers

  • 27779-68-6
  • 62-46-4

System Generated Number

  • 0001077287

Structure Descriptors

InChI

1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

InChIKey

AGBQKNBQESQNJD-UHFFFAOYSA-N

Smiles

C1[C@@H](SSC1)CCCCC(O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 160mg/kg (160mg/kg)   Drugs in Japan Vol. 6, Pg. 454, 1982.
mouse LD50 intraperitoneal 235mg/kg (235mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 284, 1971.
mouse LD50 intravenous 197mg/kg (197mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 60, Pg. 278, 1964.
mouse LD50 oral 502mg/kg (502mg/kg)   Archives of Toxicology. Vol. 41, Pg. 79, 1978.
mouse LD50 subcutaneous 200mg/kg (200mg/kg)   Drugs in Japan Vol. 6, Pg. 454, 1982.
rat LD50 intraperitoneal 200mg/kg (200mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972.
rat LD50 intravenous 180mg/kg (180mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972.
rat LD50 oral 1130mg/kg (1130mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972.
rat LD50 subcutaneous 230mg/kg (230mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 60.5 deg C   EXP
Boiling Point 162.5 deg C   EXP
log P (octanol-water) 3.400 (none)   EST
Water Solubility 127 mg/L 25 EST
Vapor Pressure 3.75E-05 mm Hg 25 EST
Henry's Law Constant 1.64E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.52E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.