Compound Summary
Compound Information
dl-Thioctic acid
Compound Name: | dl-Thioctic acid |
Compound CID: | 864 |
Synonyms: | dl-Thioctic acid thioctic acid alpha-Lipoic acid 1077-28-7 5-(1,2-Dithiolan-3-yl)pentanoic acid More... |
Iupac Name: | 5-(dithiolan-3-yl)pentanoic acid |
InChI: | 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 |
Canonical Smiles: | C1CSSC1CCCCC(=O)O |
Isomeric Smiles: | C1CSSC1CCCCC(=O)O |
Molecular Weight: | 206.3 |
Molecular Formula: | C8H14O2S2 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
dl-Thioctic acid
Molecular Weight: | 206.3 |
Molecular Formula: | C8H14O2S2 |
Hydrogen Bond Donor Count: | 1 |
Hydrogen Bond Acceptor Count: | 4 |
Rotatable Bond Count: | 5 |
Heavy Atom Count: | 12 |
Complexity: | 150 |
Synonyms
dl-Thioctic acid
| dl-Thioctic acid | dl-Thioctic acid |
|---|---|
dl-Thioctic acid |
thioctic acid |
alpha-Lipoic acid |
1077-28-7 |
5-(1,2-Dithiolan-3-yl)pentanoic acid |
lipoic acid |
DL-alpha-Lipoic acid |
1,2-dithiolane-3-pentanoic acid |
alpha Lipoic Acid |
Thioctacid |
62-46-4 |
Biletan |
6,8-Thioctic acid |
6-Thioctic acid |
Lipothion |
dl-Lipoic acid |
DL-6,8-Thioctic acid |
5-(dithiolan-3-yl)pentanoic acid |
Liposan |
Thioctsan |
Tioctacid |
Rac-lipoate |
6,8-Dithiooctanoic acid |
alpha-Liponsaeure |
DL-6-Thioctic acid |
Thioctic acid dl-form |
alpha-liponic acid |
1,2-Dithiolane-3-valeric acid |
Thioktsaeure |
Tioctidasi |
(RS)-Lipoic acid |
5-(1,2-Dithiolan-3-yl)valeric acid |
espa-lipon |
5-(Dithiolan-3-yl)valeric acid |
Acetate-replacing factor |
6,8-Thiotic acid |
Thioctansaeure |
6-Thiotic acid |
DL-1,2-Dithiolane 3-valeric acid |
(+-)-Lipoic acid |
Thioctsaeure |
liponic acid |
Thiooctic acid |
a-lipoic acid |
DL-.alpha.-Lipoic acid |
(+/-)-1,2-Dithiolane-3-pentanoic acid |
DL-1,2-Dithiolane-3-valeric acid |
lipoate |
MFCD00005474 |
NSC 90788 |
Lipoic acid, alpha |
NSC 628502 |
(RS)-thioctic acid |
(+-)-1,2-Dithiolane-3-pentanoic acid |
.alpha.-Liponic acid |
CHEBI:16494 |
Lip(S2) |
DL-1,2-Dithiolan-3-valeriansaeure |
(.+-.)-Lipoic acid |
1,2-DITHIOLANE-3-VALERIC ACID, (+-)- |
(RS)-.alpha.-Lipoic acid |
5-3-(1,2-dithiolanyl)pentanoic acid |
CHEMBL33864 |
(.+-.)-.alpha.-Lipoic acid |
NSC90788 |
NSC-90788 |
NCGC00016032-06 |
DSSTox_CID_5508 |
Protogen A |
(+/-)-alpha-Lipoic acid |
DSSTox_RID_77816 |
DSSTox_GSID_25508 |
Berlition |
Thiogamma |
(R)-(+)-alpha-Lipoic acid;R-(+)-Thioctic acid |
L-Thioctic acid |
Thioktsaeure German |
biomolipon |
duralipon |
Alipure |
AlphaLipogamma |
Thiotacid |
biomo lipon |
espa lipon |
Alpha Lipogamma |
Alpha-Lipogamma |
Pyruvate oxidation factor |
DL-Thiocticacid |
Pleomix Alpha |
Thioctacide T |
Verla Lipon |
AlphaLipon Stada |
.alpha.-Lipoic acid |
Alpha Lippon AL |
alpha-Liponsaeure German |
Alpha Lipon Stada |
Alpha-Lipon Stada |
5-(1,2)Dithiolan-3-yl-pentanoic acid |
5-1,2Dithiolan-3-yl-pentanoic acid |
Liponsaureratiopharm |
alpha-lipon 300 |
SMR000058198 |
CAS-1077-28-7 |
Liponsaure-ratiopharm |
(+-)-Thioctic acid |
alpha Liponsaure von ct |
Tioctidasi acetate replacing factor |
SR-01000737460 |
(RS)-alpha-Lipoic acid |
EINECS 200-534-6 |
EINECS 214-071-2 |
(+-)-alpha-lipoic acid |
BRN 0081853 |
BRN 0122410 |
Alpha Lipoic |
Alphalipoic-acid |
DL-1,2-Dithiolan-3-valeriansaeure German |
Thioctic acid INN:BAN:JAN |
HSDB 7818 |
alpha-lipoic-acid |
D,L-Lipoic acid |
Thiotomin (TN) |
DL-a-Lipoic acid |
D,L-Thioctic acid |
lipoic acid (LA) |
LIPOIC-ACID |
Thioctic acid (JAN) |
()-alpha-Lipoic acid |
Spectrum_001618 |
5-(1,2-dithiolan-3-yl)-pentanoate |
Thioctic acid, dl-form |
R-(+)-alpaLipoic acid |
1,2-Dithiolane-3-pentanoic acid, (+-)- |
Spectrum2_001605 |
Spectrum3_001188 |
Spectrum4_000217 |
Spectrum5_001298 |
(S)-(-)-Thiocticacid |
(+/-)-a-Lipoic acid |
cid_864 |
(.+-.)-Thioctic acid |
Lipoic acid, alpha NF |
ACMC-209ug2 |
bmse000542 |
Epitope ID:150922 |
(+/-)-?-Lipoic acid |
(.+/-.)-Lipoic acid |
ACMC-1BU44 |
SCHEMBL51065 |
BSPBio_002835 |
DL-Thioctic acid (oxidized) |
KBioGR_000853 |
KBioSS_002098 |
5-19-07-00237 (Beilstein Handbook Reference) |
MLS000069736 |
MLS001332379 |
MLS001332380 |
MLS002153365 |
DivK1c_000912 |
SPECTRUM1503941 |
(R)-(+)- a-Lipoic acid |
SPBio_001609 |
DTXSID7025508 |
BDBM10515 |
HMS502N14 |
KBio1_000912 |
KBio2_002098 |
KBio2_004666 |
KBio2_007234 |
KBio3_002335 |
NINDS_000912 |
thioctic acid (alpha-lipoic acid) |
HMS1922M22 |
HMS3649H08 |
HMS3885I16 |
Pharmakon1600-01503941 |
ACT14091 |
ALBB-030318 |
BCP13221 |
BCP14048 |
BCP18944 |
HY-N0492 |
Tox21_110285 |
Tox21_201808 |
Tox21_303092 |
AC7875 |
BBL013878 |
CCG-39063 |
dl-1,2-Dithiolane-3-pentanoic acid |
NSC628502 |
NSC758651 |
s3996 |
SBB003484 |
STK801969 |
()-1,2-Dithiolane-3-pentanoic acid |
AKOS000121582 |
AKOS016339634 |
Tox21_110285_1 |
AB09328 |
AM84329 |
CS-4370 |
EBD2203019 |
KS-1322 |
LS40210 |
MCULE-1034910084 |
NSC-628502 |
NSC-758651 |
SB49517 |
IDI1_000912 |
DL-THIOCTIC ACID (OXIDIZED) 25G |
NCGC00016032-02 |
NCGC00016032-03 |
NCGC00016032-04 |
NCGC00016032-05 |
NCGC00016032-07 |
NCGC00016032-08 |
NCGC00016032-09 |
NCGC00016032-11 |
NCGC00016032-14 |
NCGC00090872-01 |
NCGC00090872-02 |
NCGC00090872-03 |
NCGC00090872-04 |
NCGC00090872-05 |
NCGC00256970-01 |
NCGC00259357-01 |
(+/-)-alpha-Lipoic acid, >=98.0% |
AC-22673 |
BP-31070 |
NCI60_042014 |
O217 |
R)-(+)-|A-Lipoic acid OOEthyAoEthAEa |
ST073359 |
SY010902 |
(R)-(+)-(c) paragraph sign-Lipoic acid |
SBI-0051871.P002 |
5-(1,2-Dithiolan-3-yl)pentanoic acid # |
AB0010770 |
DB-050522 |
( inverted exclamation markA)-a-Lipoic acid |
1,2-Dithiolane-3-pentanoic acid, (+/-)- |
1,2-Dithiolane-3-valeric acid, (.+-.)- |
FT-0622068 |
FT-0625429 |
FT-0670812 |
FT-0670813 |
L0058 |
1,2-Dithiolane-3-pentanoic acid, (.+-.)- |
1,2-Dithiolane-3-valeric acid, (.+/-.)- |
1,2-Dithiolane-3-pentanoic acid, (.+/-.)- |
3049-EP2316827A1 |
C00725 |
D00086 |
J10446 |
AB00052393_09 |
(+/-)?-?1,2-?Dithiolane-?3-?Pentanoic Acid |
A801751 |
Q312229 |
1,2-Dithiolane-3-pentanoic acid, (+-)- (9CI) |
J-002007 |
J-520421 |
SR-01000737460-2 |
SR-01000737460-6 |
F2191-0208 |
Thioctic acid, European Pharmacopoeia (EP) Reference Standard |
(+/-)-alpha-Lipoic acid, BioReagent, cell culture tested, >=99% |
(+/-)-alpha-Lipoic acid, synthetic, >=99% (titration), powder |
Alpha Lipoic Acid, United States Pharmacopeia (USP) Reference Standard |
(R)-(+)-1,2-Dithiolane-3-pentanoic acid; R-(+)-Thioctic acid; R-(+)-alpha-Lipoic acid |
AfAEA centa notA inverted exclamation markAfasAA|AfAEAdaggeratrade mark?-Lipoic Acid |
Thioctic acid containing impurity B, European Pharmacopoeia (EP) Reference Standard |
Thioctic acid for system suitability, European Pharmacopoeia (EP) Reference Standard |
Thioctic Acid;1,2-Dithiolane-3-pentanoic acid;5-(1,2-Dithiolan-3-yl)valeric acid |
Experimental Data
dl-Thioctic acid
| Species | Dosage | Unit | CG Lifespan(AVG/MED days) | TG Lifespan(AVG/MED days) | Lifespan Change(AVG/MED%) | CG Lifespan(MAX days) | TG Lifespan(MAX days) | Lifespan Change(MAX%) | Significant | Strain | Gender | PubMed | Active Label |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Rattus norvegicus | 1.5 | g/kg | NS | 18486188 | Inactive | ||||||||
| Caenorhabditis elegans | 1 | mM | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 100 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50 | umol/L | -3.88 | Unclear | N2 | 33683565 | |||||||
| Caenorhabditis elegans | 500 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 5 | mM | -29.28 | Unclear | N2 | 33683565 | |||||||
| Caenorhabditis elegans | 200 | umol/L | 6.76 | Unclear | N2 | 33683565 | |||||||
| Caenorhabditis elegans | 47 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 10 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 100 | umol/L | 9.63 | Unclear | N2 | 33683565 | |||||||
| Caenorhabditis elegans | 233 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Drosophila melanogaster | 0.5 | mM | 36 | 40 | 0.11 | S | w1118 | FEMALES | 32648369 | Active | |||
| Drosophila melanogaster | 0.5 | mM | 43 | 48 | 0.12 | S | Canton-S | FEMALES | 32648369 | Active | |||
| Drosophila melanogaster | 0.5 | mM | 36 | 46 | 0.28 | S | Canton-S | FEMALES | 32648369 | Active | |||
| Caenorhabditis elegans | 1 | mM | 15 | 17 | 0.13 | S | N2 | 18755260 | Active | ||||
| Caenorhabditis elegans | 200 | umol/L | 14 | 14 | 0 | NS | N2 | 18755260 | Inactive | ||||
| Caenorhabditis elegans | 1 | mM | 15 | 17 | 0.13 | NS | N2 | 18755260 | Inactive | ||||
| Caenorhabditis elegans | 5 | mM | 14 | 11 | -0.21 | S | N2 | 18755260 | Inactive | ||||
| Caenorhabditis elegans | 100 | umol/L | 15 | 16 | 0.07 | NS | N2 | 18755260 | Inactive | ||||
| Caenorhabditis elegans | 1 | mM | 14 | 16 | 0.14 | S | N2 | 18755260 | Active | ||||
| Caenorhabditis elegans | 25 | umol/L | 24.2 | 14.3 | S | N2 | 33683565 | Active | |||||
| Caenorhabditis elegans | 1 | mM | 11 | 16 | 0.45 | S | N2 | 18755260 | Active | ||||
| Caenorhabditis elegans | 50 | umol/L | 15 | 16 | 0.07 | NS | N2 | 18755260 | Inactive | ||||
| Caenorhabditis elegans | 1 | mM | 14 | 18 | 0.29 | S | N2 | 18755260 | Active |
Experimental Data Visualization
dl-Thioctic acid
Statistics Data
dl-Thioctic acid
| Species | Lifespan Change(AVG/MED%) | Lifespan Change(MAX%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | 24.2 | 14.3 | 2 | 21 |
| Drosophila melanogaster | 0.28 | 1 | 3 | |
| Rattus norvegicus | 1 | 1 |
Statistics Data Visualization
dl-Thioctic acid
