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MedKoo Cat#: 330191 | Name: (R)-Dihydrolipoic acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

(R)-Dihydrolipoic acid is a R-isomer of Dihydrolipoic acid. Dihydrolipoic acid, also know as DHLA, is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups, and therefore is a dithiol. It is optically active, but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.

Chemical Structure

(R)-Dihydrolipoic acid
(R)-Dihydrolipoic acid
CAS#119365-69-4

Theoretical Analysis

MedKoo Cat#: 330191

Name: (R)-Dihydrolipoic acid

CAS#: 119365-69-4

Chemical Formula: C8H16O2S2

Exact Mass: 208.0592

Molecular Weight: 208.33

Elemental Analysis: C, 46.12; H, 7.74; O, 15.36; S, 30.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
(R)-Dihydrolipoic acid; Dihydrolipoic acid, R; (R)-DHLA; (6R)-DHLA;
IUPAC/Chemical Name
(6R)-6,8-Dimercaptooctanoic acid
InChi Key
IZFHEQBZOYJLPK-SSDOTTSWSA-N
InChi Code
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
SMILES Code
O=C(O)CCCC[C@@H](S)CCS
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 208.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Oláh Z, Vogg ATJ, Kremmer T, Szűcs Z, Varga Z, Dóczi R. Optimization of the reduction of (74)As(V) to (74)As(III) and of the labelling of dithiol dihydrolipoic acid. Appl Radiat Isot. 2019 Jul;149:75-82. doi: 10.1016/j.apradiso.2019.04.004. Epub 2019 Apr 15. PubMed PMID: 31029937. 2: Ren SH, Liu SG, Ling Y, Li NB, Luo HQ. Facile method for iodide ion detection via the fluorescence decrease of dihydrolipoic acid/beta-cyclodextrin protected Ag nanoclusters. Spectrochim Acta A Mol Biomol Spectrosc. 2019 Apr 5;212:199-205. doi: 10.1016/j.saa.2019.01.009. Epub 2019 Jan 4. PubMed PMID: 30639913. 3: Micillo R, Sirés-Campos J, García-Borrón JC, Panzella L, Napolitano A, Olivares C. Conjugation with Dihydrolipoic Acid Imparts Caffeic Acid Ester Potent Inhibitory Effect on Dopa Oxidase Activity of Human Tyrosinase. Int J Mol Sci. 2018 Jul 24;19(8). pii: E2156. doi: 10.3390/ijms19082156. PubMed PMID: 30042336; PubMed Central PMCID: PMC6121902. 4: Zhou K, Enkhjargal B, Xie Z, Sun C, Wu L, Malaguit J, Chen S, Tang J, Zhang J, Zhang JH. Dihydrolipoic Acid Inhibits Lysosomal Rupture and NLRP3 Through Lysosome-Associated Membrane Protein-1/Calcium/Calmodulin-Dependent Protein Kinase II/TAK1 Pathways After Subarachnoid Hemorrhage in Rat. Stroke. 2018 Jan;49(1):175-183. doi: 10.1161/STROKEAHA.117.018593. PubMed PMID: 29273596; PubMed Central PMCID: PMC5744882. 5: Wang B, Chen X, Wang Z, Xiong W, Xu T, Zhao X, Cao Y, Guo Y, Li L, Chen S, Huang S, Wang X, Fang M, Shen Z. Aldehyde dehydrogenase 1A1 increases NADH levels and promotes tumor growth via glutathione/dihydrolipoic acid-dependent NAD(+) reduction. Oncotarget. 2017 May 8;8(40):67043-67055. doi: 10.18632/oncotarget.17688. eCollection 2017 Sep 15. PubMed PMID: 28978015; PubMed Central PMCID: PMC5620155. 6: García-Cortés M, Fernández-Argüelles MT, Costa-Fernández JM, Sanz-Medel A. Sensitive prostate specific antigen quantification using dihydrolipoic acid surface-functionalized phosphorescent quantum dots. Anal Chim Acta. 2017 Sep 22;987:118-126. doi: 10.1016/j.aca.2017.08.003. Epub 2017 Aug 13. PubMed PMID: 28916035. 7: Regiart M, Fernández-Baldo MA, Villarroel-Rocha J, Messina GA, Bertolino FA, Sapag K, Timperman AT, Raba J. Microfluidic immunosensor based on mesoporous silica platform and CMK-3/poly-acrylamide-co-methacrylate of dihydrolipoic acid modified gold electrode for cancer biomarker detection. Anal Chim Acta. 2017 Apr 22;963:83-92. doi: 10.1016/j.aca.2017.01.029. Epub 2017 Jan 30. PubMed PMID: 28335979. 8: Bilska-Wilkosz A, Gorny M, Dudek M, Nowinski L, Bednarski M, Iciek M, Kowalczyk-Pachel D, Sokolowska-Jezewicz M, Filipek B, Wlodek L. INACTIVATION OF ALDEHYDE DEHYDROGENASE BY NITROGLYCERIN IN THE PRESENCE AND ABSENCE OF LIPOIC ACID AND DIHYDROLIPOIC ACID. IMPLICATIONS FOR THE PROBLEM OF DIFFERENTIAL EFFECTS OF LIPOIC ACID IN VITRO AND IN VIVO. Acta Pol Pharm. 2016 Nov;73(6):1531-1538. PubMed PMID: 29634107. 9: Zadehvakili B, McNeill SM, Fawcett JP, Giles GI. The design of redox active thiol peroxidase mimics: Dihydrolipoic acid recognition correlates with cytotoxicity and prooxidant action. Biochem Pharmacol. 2016 Mar 15;104:19-28. doi: 10.1016/j.bcp.2016.01.012. Epub 2016 Jan 19. PubMed PMID: 26801688. 10: Khan MI, Iqbal Z, Khan A. Simultaneous determination of the endogenous free α-lipoic acid and dihydrolipoic acid in human plasma and erythrocytes by RP-HPLC coupled with electrochemical detector. Methods Mol Biol. 2015;1208:345-60. doi: 10.1007/978-1-4939-1441-8_25. PubMed PMID: 25323519. 11: Castañeda-Arriaga R, Alvarez-Idaboy JR. Lipoic acid and dihydrolipoic acid. A comprehensive theoretical study of their antioxidant activity supported by available experimental kinetic data. J Chem Inf Model. 2014 Jun 23;54(6):1642-52. doi: 10.1021/ci500213p. Epub 2014 Jun 10. PubMed PMID: 24881907. 12: Wijayanti HB, Oh HE, Sharma R, Deeth HC. Reduction of aggregation of β-lactoglobulin during heating by dihydrolipoic acid. J Dairy Res. 2013 Nov;80(4):383-9. doi: 10.1017/S0022029913000332. Epub 2013 Jul 19. PubMed PMID: 23866304. 13: Liu J, Song E, Liu L, Ma X, Tian X, Dong H, Song Y. Polychlorinated biphenyl quinone metabolites lead to oxidative stress in HepG2 cells and the protective role of dihydrolipoic acid. Toxicol In Vitro. 2012 Sep;26(6):841-8. doi: 10.1016/j.tiv.2012.04.028. Epub 2012 May 8. PubMed PMID: 22580158. 14: Bérczi A, Zimányi L, Asard H. Dihydrolipoic acid reduces cytochrome b561 proteins. Eur Biophys J. 2013 Mar;42(2-3):159-68. doi: 10.1007/s00249-012-0812-x. Epub 2012 Apr 20. PubMed PMID: 22526465. 15: Houng WL, Lin CA, Shen JL, Yeh HI, Wang HH, Chang WH, Chan WH. Dihydrolipoic acid induces cytotoxicity in mouse blastocysts through apoptosis processes. Int J Mol Sci. 2012;13(3):3988-4002. doi: 10.3390/ijms13033988. Epub 2012 Mar 22. PubMed PMID: 22489194; PubMed Central PMCID: PMC3317754. 16: Zhao F, Liu ZQ. Comparison of antioxidant effectiveness of lipoic acid and dihydrolipoic acid. J Biochem Mol Toxicol. 2011 Jul-Aug;25(4):216-23. doi: 10.1002/jbt.20378. Epub 2010 Dec 10. PubMed PMID: 21812071. 17: Laurino P, Kikkeri R, Seeberger PH. Continuous-flow reactor-based synthesis of carbohydrate and dihydrolipoic acid-capped quantum dots. Nat Protoc. 2011 Jul 28;6(8):1209-20. doi: 10.1038/nprot.2011.357. PubMed PMID: 21799489. 18: Mikami Y, Shibuya N, Kimura Y, Nagahara N, Ogasawara Y, Kimura H. Thioredoxin and dihydrolipoic acid are required for 3-mercaptopyruvate sulfurtransferase to produce hydrogen sulfide. Biochem J. 2011 Nov 1;439(3):479-85. doi: 10.1042/BJ20110841. PubMed PMID: 21732914. 19: Khan A, Iqbal Z, Watson DG, Khan A, Khan I, Muhammad N, Muhammad S, Nasib HA, Iqbal N, Faiz-Ur-Rehman, Kashif M. Simultaneous determination of lipoic acid (LA) and dihydrolipoic acid (DHLA) in human plasma using high-performance liquid chromatography coupled with electrochemical detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Jun 15;879(20):1725-31. doi: 10.1016/j.jchromb.2011.04.017. Epub 2011 Apr 22. PubMed PMID: 21550862. 20: Chan WH, Houng WL, Lin CA, Lee CH, Li PW, Hsieh JT, Shen JL, Yeh HI, Chang WH. Impact of dihydrolipoic acid on mouse embryonic stem cells and related regulatory mechanisms. Environ Toxicol. 2013 Feb;28(2):87-97. doi: 10.1002/tox.20700. Epub 2011 Apr 1. PubMed PMID: 21462292.