Basic information
- CAS
462-20-4- Standard SMILES
O=C(O)CCCCC(S)CCS- InChIKey
IZFHEQBZOYJLPK-UHFFFAOYSA-N- Molecular formula
- C8H16O2S2
- Average molar mass
- 208.3 g/mol
- Monoisotopic mass
- 208.05917175
Overview
Dihydrolipoic acid is a thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects. It has a role as an antioxidant, a neuroprotective agent and a human metabolite. It is functionally related to an octanoic acid. It is a conjugate acid of a dihydrolipoate.
Names & identifiers
- Preferred name
- Dihydrolipoic Acid
- IUPAC
- 6,8-bis(sulfanyl)octanoic acid
- English name
- Dihydrolipoic acid
- Molecular formula
- C8H16O2S2
- Molecular weight
- 208.34
Names & synonyms
Dihydrolipoic acid462-20-46,8-Dimercaptooctanoic acidDihydrothioctic acid6,8-disulfanyloctanoic acid6,8-Dihydrothioctic acid6,8-bis(sulfanyl)octanoic acidThioctic acid, dihydro-6,8-bis-sulfanyloctanoic acidOCTANOIC ACID, 6,8-DIMERCAPTO-7NV2KHU5JACHEBI:18047
Show more names
dihydrolipoateLIPOIC ACID, REDUCED6,8-DIMERCAPTO-OCTANOIC ACIDusafxr-12USAF XR-12Dihydroliponsurereducedlipoicaciddihydro-lipoicaci
DTXSID50861946RefChem:133863DTXCID70810794610-288-5675-983-8DihydrolipoicacidDHLAReduced lipoic acid
Database identifiers
- CAS
462-20-4- PubChem CID
- 421
- DTXSID
DTXSID50861946- ChEMBL
CHEMBL1235647- ChEBI
CHEBI:18047- UNII
- 7NV2KHU5JA
- EC Number
- 610-288-5
- Nikkaji
- J86.722E
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 39.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 128
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 62 °C · 62 °C
- Boiling point
- 161.5 °C · 161.5 °C(Press: 0.7 Torr)
- Density
- 1.132 g/cm3 · 1.132 g/cm3
- vapor pressure
- 0 Pa · 0Pa at 25℃
- refractive index
- 1.522 · 1.5220-1.5260
- storage temp.
- 2 C · +2C to +8C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- liquid
- pka
- 4.74 · 4.74±0.10(Predicted)
- color
- light yellow
- InChI
- InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
- InChIKey
- IZFHEQBZOYJLPK-UHFFFAOYSA-N
- SMILES
- C(O)(=O)CCCCC(S)CCS
- LogP
- 1.9 at · 1.9 at 20℃
- Surface tension
- 53.6 mN/m · 53.6mN/m at 1.02g/L and 21℃
- FDA UNII
- 7 NV2KHU5JA · 7NV2KHU5JA
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS09
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H317-H318-H411
- Precautionary statements
- 261 · P261-P273-P280-P301+P312-P302+P352-P305+P351+P338
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 525000 · RH0525000
- HS Code
- 2930.9 · 2930.90.4950
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2Skin Sens. 1
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 26-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11996
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- rtecs
- RH0525000
- hs_code
- 2930.90.4950
- risk_code
- 36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS09
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302-H315-H317-H318-H411
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2Skin Sens. 1
- Precautionary statements
- P261-P273-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Cellular LocationsExtracellular
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Applications
Usesγ-Lipoic Acid, is a metabolite of α-Lipoic Acid (L468730), which is a over-the-counter nutritional supplements, that has been used as antioxidant. It is also fat-metabolism stimulator, and thus used a "weight loss" and "energy" supplement.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
河南赢创生物科技有限公司16650615803 · [email protected]
北京科迈启医药科技有限公司15910349257 15910349257 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
南京望知星医药科技有限公司18569809817 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
希瓦生物科技（广州）有限公司13268215580 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
United Life Science020-82099279 18988941402 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
上海相辉医药科技有限公司13761987713; 13761987713 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
Moxin Chemicals+86-17320513646 +86-17320513646 · [email protected]
杭州云易国科生物科技有限公司18457506494 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
北京奥秘佳得医药科技有限公司+86-13522808617 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
深圳摩科生化科技有限公司18627923403 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
普善实业（陕西）有限公司029-81310890 18165209495 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
成都赛诺宁科技有限公司28-87999436 02887999436 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
广东翁江化学试剂有限公司0751-2886766 13927870850 · [email protected]
上海玻尔化学试剂有限公司19102157732 · [email protected]
深圳卓越生物医药科技有限公司0755-26050679 18318671572 · [email protected]
山东利腾生物科技有限公司15020019777 18663721413 · [email protected]
Standardpharm Co. Ltd.86-714-3992388 · [email protected]
艾吉析科技（上海）有限公司17721401538;17717235263 17721401538 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
启源（广东）医药化工有限公司18026564465 · [email protected]
四川普西奥标物科技有限公司13540909846 13882008651 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
成都叮当时代医药科技有限公司028-86040038 · [email protected]
Additional notes
DefinitionChEBI: A thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.
Related reactions
14 records
Compound notes
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