Lipoic Acid | CAS#1200-22-2 | 1077-28-7 | Organosulfur

MedKoo Cat#: 318155 | Name: Lipoic Acid

Description:

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

Lipoic Acid, also known as R-(+)-alpha-Lipoic acid, is an organosulfur compound derived from octanoic acid. It is made in animals normally, and is essential for aerobic metabolism. It is also manufactured and is available as a dietary supplement in some countries where it is marketed as an antioxidant, and is available as a pharmaceutical drug in other countries.

Chemical Structure

Lipoic Acid

CAS#1200-22-2

Theoretical Analysis

MedKoo Cat#: 318155

Name: Lipoic Acid

CAS#: 1200-22-2

Chemical Formula: C8H14O2S2

Exact Mass: 206.0435

Molecular Weight: 206.32

Elemental Analysis: C, 46.57; H, 6.84; O, 15.51; S, 31.08

Price and Availability

Size	Price	Availability
5g	USD 150.00	Ready to ship
10g	USD 250.00	Ready to ship
100g	USD 650.00	Ready to ship
500g	USD 1,950.00	Ready to ship

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Related CAS #

1077-28-7 (racemic) 1200-22-2

Synonym

Lipoic Acid; R-(+)-alpha-Lipoic acid; (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid; (+)-alpha-Lipoic acid; Lipoate;Verla Lipon; Verla-Lipon; VerlaLipon;Thioctacide T; Thioctic Acid; Thiogamma Injekt; Thiogamma oral; thioctic acid;

IUPAC/Chemical Name

(R)-5-(1,2-dithiolan-3-yl)pentanoic acid

InChi Key

AGBQKNBQESQNJD-SSDOTTSWSA-N

InChi Code

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1

SMILES Code

O=C(O)CCCC[C@@H]1CCSS1

Appearance

Light yellow to dark brown 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, not in water

Shelf Life

>2 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

Alpha lipoic acid combined with epalrestat: a therapeutic option for patients with diabetic peripheral neuropathy. The molecular nature of lipoic acid (LA) clarifies its capability of taking part to a variety of biochemical reactions where redox state is meaningful. The pivotal action of LA is the antioxidant activity due to its ability to scavenge and inactivate free radicals. Furthermore, LA has been shown to chelate toxic metals both directly and indirectly by its capability to enhance intracellular glutathione (GSH) levels. This last property is due to its ability to interact with GSH and recycle endogenous GSH. LA exhibits significant antioxidant activity protecting against oxidative damage in several diseases, including neurodegenerative disorders. Interestingly, LA is unique among natural antioxidants for its capability to satisfy a lot of requirements, making it a potentially highly effective therapeutic agent for many conditions related with oxidative damage. In particular, there are evidences showing that LA has therapeutic activity in lowering glucose levels in diabetic conditions. Similarly, LA supplementation has multiple beneficial effects on the regression of the mitochondrial function and on oxidative stress associated with several diseases and aging.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#B7B11C08

QC Data

View QC data: current batch, Lot#B7B11C08

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Lipoic acid ((R)-(+)-α-Lipoic acid) is an antioxidant, which is an essential cofactor of mitochondrial enzyme complexes.

In vitro activity:

As shown in Figure 8c, the KRT10 gene promotes the expression of differentiation biomarkers and plays a role in maintaining skin homeostasis. In particular, it is affected by the formation of the stratum corneum cell membrane. KRT10 was expected to produce an effect similar to that of the IVL gene, because KRT10 is expressed in large amounts through which a large amount of keratinous cell membrane is formed. Expression appears to be similar to the IVL gene expression phenomenon presented in Figure 8b. The increase in gene expression after ALA (α-Lipoic acid) treatment was the highest in the group at day 3 after treatment with 1 μM ALA. This is the same phenomenon observed for IVL (involucrin). In general, when ALA treatment was performed, the expression was lower than that in the control. Reference: Int J Mol Sci. 2021 Feb; 22(4): 2160. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7927099/

In vivo activity:

Given the essential role of inflammation in tauopathy, this study next examined the levels of inflammatory markers and pro-inflammatory proteins in P301S mice. As shown in Fig. 2B, high-dose LA (lipoic acid) treatment markedly down-regulated the levels of GFAP, TNFα and IL-1β compared to the levels in vehicle-treated mice (Fig. 2B, C-F, p < 0.05). GFAP immunoreactivity also exhibited a significant decrease in the cortex and hippocampus of high-dose LA-treated mice (Fig. 2A, p < 0.05). However, LA treatment did not significantly decrease the level of Iba1 (Fig. 2B, D, p > 0.05). Reference: Redox Biol. 2018 Apr; 14: 535–548. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5684493/

	Solvent	mg/mL	mM
Solubility
	DMSO	57.0	276.27
	DMF	30.0	145.41
	Ethanol	30.0	145.41
	Ethanol:PBS (pH 7.2) (1:8)	0.3	1.21

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 206.32 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.

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

Formulation protocol:

1. Kim K, Kim J, Kim H, Sung GY. Effect of α-Lipoic Acid on the Development of Human Skin Equivalents Using a Pumpless Skin-on-a-Chip Model. Int J Mol Sci. 2021 Feb 22;22(4):2160. doi: 10.3390/ijms22042160. PMID: 33671528; PMCID: PMC7927099. 2. Tai S, Zheng Q, Zhai S, Cai T, Xu L, Yang L, Jiao L, Zhang C. Alpha-Lipoic Acid Mediates Clearance of Iron Accumulation by Regulating Iron Metabolism in a Parkinson's Disease Model Induced by 6-OHDA. Front Neurosci. 2020 Jun 25;14:612. doi: 10.3389/fnins.2020.00612. PMID: 32670009; PMCID: PMC7330090. 3. Joksimovic SL, Lamborn N, Jevtovic-Todorovic V, Todorovic SM. Alpha lipoic acid attenuates evoked and spontaneous pain following surgical skin incision in rats. Channels (Austin). 2021 Dec;15(1):398-407. doi: 10.1080/19336950.2021.1907058. PMID: 33843451; PMCID: PMC8043189. 4. Zhang YH, Wang DW, Xu SF, Zhang S, Fan YG, Yang YY, Guo SQ, Wang S, Guo T, Wang ZY, Guo C. α-Lipoic acid improves abnormal behavior by mitigation of oxidative stress, inflammation, ferroptosis, and tauopathy in P301S Tau transgenic mice. Redox Biol. 2018 Apr;14:535-548. doi: 10.1016/j.redox.2017.11.001. Epub 2017 Nov 7. PMID: 29126071; PMCID: PMC5684493.

In vitro protocol:

In vivo protocol:

1. Joksimovic SL, Lamborn N, Jevtovic-Todorovic V, Todorovic SM. Alpha lipoic acid attenuates evoked and spontaneous pain following surgical skin incision in rats. Channels (Austin). 2021 Dec;15(1):398-407. doi: 10.1080/19336950.2021.1907058. PMID: 33843451; PMCID: PMC8043189. 2. Zhang YH, Wang DW, Xu SF, Zhang S, Fan YG, Yang YY, Guo SQ, Wang S, Guo T, Wang ZY, Guo C. α-Lipoic acid improves abnormal behavior by mitigation of oxidative stress, inflammation, ferroptosis, and tauopathy in P301S Tau transgenic mice. Redox Biol. 2018 Apr;14:535-548. doi: 10.1016/j.redox.2017.11.001. Epub 2017 Nov 7. PMID: 29126071; PMCID: PMC5684493.

1: Wang X, Lin H, Xu S, Jin Y, Zhang R. Alpha lipoic acid combined with epalrestat: a therapeutic option for patients with diabetic peripheral neuropathy. Drug Des Devel Ther. 2018 Sep 7;12:2827-2840. doi: 10.2147/DDDT.S168878. eCollection 2018. Review. PubMed PMID: 30233145; PubMed Central PMCID: PMC6135078. 2: Akbari M, Ostadmohammadi V, Lankarani KB, Tabrizi R, Kolahdooz F, Khatibi SR, Asemi Z. The effects of alpha-lipoic acid supplementation on glucose control and lipid profiles among patients with metabolic diseases: A systematic review and meta-analysis of randomized controlled trials. Metabolism. 2018 Oct;87:56-69. doi: 10.1016/j.metabol.2018.07.002. Epub 2018 Jul 7. Review. PubMed PMID: 29990473. 3: Akbari M, Ostadmohammadi V, Tabrizi R, Mobini M, Lankarani KB, Moosazadeh M, Heydari ST, Chamani M, Kolahdooz F, Asemi Z. The effects of alpha-lipoic acid supplementation on inflammatory markers among patients with metabolic syndrome and related disorders: a systematic review and meta-analysis of randomized controlled trials. Nutr Metab (Lond). 2018 Jun 5;15:39. doi: 10.1186/s12986-018-0274-y. eCollection 2018. Review. PubMed PMID: 29930690; PubMed Central PMCID: PMC5989440. 4: Ambrosi N, Guerrieri D, Caro F, Sanchez F, Haeublein G, Casadei D, Incardona C, Chuluyan E. Alpha Lipoic Acid: A Therapeutic Strategy that Tend to Limit the Action of Free Radicals in Transplantation. Int J Mol Sci. 2018 Jan 4;19(1). pii: E102. doi: 10.3390/ijms19010102. Review. PubMed PMID: 29300330; PubMed Central PMCID: PMC5796052. 5: Tibullo D, Li Volti G, Giallongo C, Grasso S, Tomassoni D, Anfuso CD, Lupo G, Amenta F, Avola R, Bramanti V. Biochemical and clinical relevance of alpha lipoic acid: antioxidant and anti-inflammatory activity, molecular pathways and therapeutic potential. Inflamm Res. 2017 Nov;66(11):947-959. doi: 10.1007/s00011-017-1079-6. Epub 2017 Jul 4. Review. PubMed PMID: 28676917. 6: Namazi N, Larijani B, Azadbakht L. Alpha-lipoic acid supplement in obesity treatment: A systematic review and meta-analysis of clinical trials. Clin Nutr. 2018 Apr;37(2):419-428. doi: 10.1016/j.clnu.2017.06.002. Epub 2017 Jun 8. Review. PubMed PMID: 28629898. 7: Mohammadi V, Dehghani S, Askari G. Does Alpha-lipoic Acid Supplement Regulate Blood Pressure? A Systematic Review of Randomized, Double-blind Placebo-controlled Clinical Trials. Int J Prev Med. 2017 May 11;8:33. doi: 10.4103/2008-7802.206138. eCollection 2017. Review. PubMed PMID: 28584615; PubMed Central PMCID: PMC5450615. 8: Sohaib M, Anjum FM, Nasir M, Saeed F, Arshad MS, Hussain S. Alpha-lipoic acid: An inimitable feed supplement for poultry nutrition. J Anim Physiol Anim Nutr (Berl). 2018 Feb;102(1):33-40. doi: 10.1111/jpn.12693. Epub 2017 Apr 26. Review. PubMed PMID: 28447384. 9: Kucukgoncu S, Zhou E, Lucas KB, Tek C. Alpha-lipoic acid (ALA) as a supplementation for weight loss: results from a meta-analysis of randomized controlled trials. Obes Rev. 2017 May;18(5):594-601. doi: 10.1111/obr.12528. Epub 2017 Mar 13. Review. PubMed PMID: 28295905; PubMed Central PMCID: PMC5523816. 10: Monastra G, De Grazia S, Cilaker Micili S, Goker A, Unfer V. Immunomodulatory activities of alpha lipoic acid with a special focus on its efficacy in preventing miscarriage. Expert Opin Drug Deliv. 2016 Dec;13(12):1695-1708. Epub 2016 Jun 24. Review. PubMed PMID: 27292272. 11: Huerta AE, Prieto-Hontoria PL, Sáinz N, Martínez JA, Moreno-Aliaga MJ. Supplementation with α-Lipoic Acid Alone or in Combination with Eicosapentaenoic Acid Modulates the Inflammatory Status of Healthy Overweight or Obese Women Consuming an Energy-Restricted Diet. J Nutr. 2016 Mar 9. pii: jn224105. [Epub ahead of print] Review. PubMed PMID: 26962183. 12: Moon HS. Chemopreventive Effects of Alpha Lipoic Acid on Obesity-Related Cancers. Ann Nutr Metab. 2016;68(2):137-44. doi: 10.1159/000443994. Epub 2016 Feb 2. Review. PubMed PMID: 26829711. 13: Dörsam B, Fahrer J. The disulfide compound α-lipoic acid and its derivatives: A novel class of anticancer agents targeting mitochondria. Cancer Lett. 2016 Feb 1;371(1):12-9. doi: 10.1016/j.canlet.2015.11.019. Epub 2015 Nov 18. Review. PubMed PMID: 26604131. 14: Costantino D, Guaraldi C, Costantino M, Bounous VE. [Use of alpha-lipoic acid and omega-3 in postpartum pain treatment]. Minerva Ginecol. 2015 Oct;67(5):465-73. Review. Italian. PubMed PMID: 26491825. 15: Rochette L, Ghibu S, Muresan A, Vergely C. Alpha-lipoic acid: molecular mechanisms and therapeutic potential in diabetes. Can J Physiol Pharmacol. 2015 Dec;93(12):1021-7. doi: 10.1139/cjpp-2014-0353. Epub 2015 Sep 25. Review. PubMed PMID: 26406389. 16: Pashaj A, Xia M, Moreau R. α-Lipoic acid as a triglyceride-lowering nutraceutical. Can J Physiol Pharmacol. 2015 Dec;93(12):1029-41. doi: 10.1139/cjpp-2014-0480. Epub 2015 Apr 20. Review. PubMed PMID: 26235242. 17: Roberts JL, Moreau R. Emerging role of alpha-lipoic acid in the prevention and treatment of bone loss. Nutr Rev. 2015 Feb;73(2):116-25. doi: 10.1093/nutrit/nuu005. Review. PubMed PMID: 26024498. 18: Kamchatnov PR, Abusueva BA, Kazakov AY. [Alpha-lipoic acid in treatment of nervous system diseases]. Zh Nevrol Psikhiatr Im S S Korsakova. 2014;114(10):131-5. Review. Russian. PubMed PMID: 25632426. 19: Patel MK, Riley MA, Hobbs S, Cortez-Cooper M, Robinson VJ. Can α-lipoic acid mitigate progression of aging-related decline caused by oxidative stress? South Med J. 2014 Dec;107(12):780-7. doi: 10.14423/SMJ.0000000000000198. Review. PubMed PMID: 25502159. 20: Papanas N, Ziegler D. Efficacy of α-lipoic acid in diabetic neuropathy. Expert Opin Pharmacother. 2014 Dec;15(18):2721-31. doi: 10.1517/14656566.2014.972935. Epub 2014 Nov 10. Review. PubMed PMID: 25381809.