Levocarnitine propionate | CAS#20064-19-1 | enzyme

MedKoo Cat#: 596947 | Name: Levocarnitine propionate

Featured

Description:

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

Propionylcarnitine is present in high abundance in the urine of patients with Methylmalonyl-CoA mutase (MUT) deficiency, together with Methylmalonic acid. MUT is a mitochondrial enzyme that catalyzes the isomerization of methylmalonyl-CoA to succinyl-CoA.

Chemical Structure

Levocarnitine propionate

CAS#20064-19-1

Theoretical Analysis

MedKoo Cat#: 596947

Name: Levocarnitine propionate

CAS#: 20064-19-1

Chemical Formula: C10H19NO4

Exact Mass: 217.1314

Molecular Weight: 217.27

Elemental Analysis: C, 55.28; H, 8.82; N, 6.45; O, 29.46

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 300.00	2 Weeks
50mg	USD 850.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Levocarnitine propionate; L-Propionylcarnitine; Propionyl-L-carnitine; ST 261; ST-261; ST261;

IUPAC/Chemical Name

(R)-3-(propionyloxy)-4-(trimethylammonio)butanoate

InChi Key

UFAHZIUFPNSHSL-MRVPVSSYSA-N

InChi Code

InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3/t8-/m1/s1

SMILES Code

CCC(O[C@H](CC([O-])=O)C[N+](C)(C)C)=O

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

>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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Propionylcarnitine is present in high abundance in the urine of patients with Methylmalonyl-CoA mutase (MUT) deficiency, together with Methylmalonic acid.

In vitro activity:

In the following, cells were treated with LC (L-Carnitine) and at the end of the treatment period, the cells were subjected to the real-time PCR technique along with western blotting assay for measurement of the telomere length and assessment of protein expression, respectively. The results showed that 0.2 mM LC caused the elongation of the telomere length and increased the TERT protein expression. Reference: Curr Stem Cell Res Ther. 2022 May 11. https://pubmed.ncbi.nlm.nih.gov/35546751/

In vivo activity:

Inflammation at the tissue level was also mildest in group A, and severest in the group that was not given carnitine (group C). All of the study groups and the control group differed significantly with respect to inflammation scores. In conclusion, L-carnitine improved oxygen saturation, and decreased urine leukotriene E4 levels and inflammation in lung tissues in the present murine model of asthma. Reference: Acta Med Okayama. 2002 Dec;56(6):295-301. https://pubmed.ncbi.nlm.nih.gov/12685858/

Preparing Stock Solutions

The following data is based on the product molecular weight 217.27 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. Fathi E, Montazersaheb S, Sanaat Z, Nakhlband A, Vandghanooni S, Farahzadi R, Vietor I. L-carnitine reduced cellular aging of bone marrow resident C-kit+ hematopoietic stem cells through telomere dependent pathways. Curr Stem Cell Res Ther. 2022 May 11. doi: 10.2174/1574888X17666220511141123. Epub ahead of print. PMID: 35546751. 2. Lee YG, Chou HC, Chen YT, Tung SY, Ko TL, Buyandelger B, Wen LL, Juan SH. L-Carnitine reduces reactive oxygen species/endoplasmic reticulum stress and maintains mitochondrial function during autophagy-mediated cell apoptosis in perfluorooctanesulfonate-treated renal tubular cells. Sci Rep. 2022 Mar 18;12(1):4673. doi: 10.1038/s41598-022-08771-3. PMID: 35304586; PMCID: PMC8933466. 3. Dehghani A, Pourjafari F, Koohkan F, Haghpanh T, Pourjafari F, Sheibani V, Afarinesh MR. L-carnitine attenuates acoustic startle reflex dysfunction in adult male rats exposed to mancozeb. Toxicol Ind Health. 2023 Jan 17:7482337231151739. doi: 10.1177/07482337231151739. Epub ahead of print. PMID: 36650049. 4. Uzuner N, Kavukçu S, Yilmaz O, Ozkal S, Işlekel H, Karaman O, Soylu A, Kargi A. The role of L-carnitine in treatment of a murine model of asthma. Acta Med Okayama. 2002 Dec;56(6):295-301. doi: 10.18926/AMO/31692. PMID: 12685858.

In vitro protocol:

In vivo protocol:

1. Dehghani A, Pourjafari F, Koohkan F, Haghpanh T, Pourjafari F, Sheibani V, Afarinesh MR. L-carnitine attenuates acoustic startle reflex dysfunction in adult male rats exposed to mancozeb. Toxicol Ind Health. 2023 Jan 17:7482337231151739. doi: 10.1177/07482337231151739. Epub ahead of print. PMID: 36650049. 2. Uzuner N, Kavukçu S, Yilmaz O, Ozkal S, Işlekel H, Karaman O, Soylu A, Kargi A. The role of L-carnitine in treatment of a murine model of asthma. Acta Med Okayama. 2002 Dec;56(6):295-301. doi: 10.18926/AMO/31692. PMID: 12685858.

1: Ghonimy A, Zhang DM, Farouk MH, Wang Q. The Impact of Carnitine on Dietary Fiber and Gut Bacteria Metabolism and Their Mutual Interaction in Monogastrics. Int J Mol Sci. 2018 Mar 28;19(4). pii: E1008. doi: 10.3390/ijms19041008. Review. PubMed PMID: 29597260; PubMed Central PMCID: PMC5979481. 2: Lindquist C, Bjørndal B, Rossmann CR, Svardal A, Hallström S, Berge RK. A fatty acid analogue targeting mitochondria exerts a plasma triacylglycerol lowering effect in rats with impaired carnitine biosynthesis. PLoS One. 2018 Mar 28;13(3):e0194978. doi: 10.1371/journal.pone.0194978. eCollection 2018. PubMed PMID: 29590220; PubMed Central PMCID: PMC5874065. 3: Laguna JG, Cardoso MS, Lima JA, Reis RB, Carvalho AU, Saturnino HM, Teixeira SMR. Expression of hepatic genes related to energy metabolism during the transition period of Holstein and F(1) Holstein-Gir cows. J Dairy Sci. 2017 Dec;100(12):9861-9870. doi: 10.3168/jds.2016-12459. Epub 2017 Sep 28. PubMed PMID: 28964523. 4: Pan H, Li LY, Li JM, Wang WL, Limbu SM, Degrace P, Li DL, Du ZY. Inhibited fatty acid β-oxidation impairs stress resistance ability in Nile tilapia (Oreochromis niloticus). Fish Shellfish Immunol. 2017 Sep;68:500-508. doi: 10.1016/j.fsi.2017.07.058. Epub 2017 Jul 31. PubMed PMID: 28774846. 5: Porter C, Constantin-Teodosiu D, Constantin D, Leighton B, Poucher SM, Greenhaff PL. Muscle carnitine availability plays a central role in regulating fuel metabolism in the rodent. J Physiol. 2017 Sep 1;595(17):5765-5780. doi: 10.1113/JP274415. Epub 2017 Jul 16. PubMed PMID: 28605113; PubMed Central PMCID: PMC5577538. 6: Szabó K, Nagy Z, Juhász V, Zolnerciks JK, Csorba A, Tímár Z, Molnár É, Pádár P, Johnson W, Beéry E, Krajcsi P. Species specificity profiling of rat and human organic cation/carnitine transporter Slc22a5/SLC22A5 (Octn2/OCTN2). Drug Metab Pharmacokinet. 2017 Jun;32(3):165-171. doi: 10.1016/j.dmpk.2016.08.005. Epub 2016 Aug 26. PubMed PMID: 28365301. 7: Liepinsh E, Makarova E, Sevostjanovs E, Hartmane D, Cirule H, Zharkova-Malkova O, Grinberga S, Dambrova M. Carnitine and γ-Butyrobetaine Stimulate Elimination of Meldonium due to Competition for OCTN2-mediated Transport. Basic Clin Pharmacol Toxicol. 2017 May;120(5):450-456. doi: 10.1111/bcpt.12729. Epub 2017 Jan 10. PubMed PMID: 27983775. 8: Manoli I, Sloan JL, Venditti CP. Isolated Methylmalonic Acidemia. 2005 Aug 16 [updated 2016 Dec 1]. In: Adam MP, Ardinger HH, Pagon RA, Wallace SE, Bean LJH, Stephens K, Amemiya A, editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2018. Available from http://www.ncbi.nlm.nih.gov/books/NBK1231/ PubMed PMID: 20301409. 9: Witters P, Debbold E, Crivelly K, Vande Kerckhove K, Corthouts K, Debbold B, Andersson H, Vannieuwenborg L, Geuens S, Baumgartner M, Kozicz T, Settles L, Morava E. Autism in patients with propionic acidemia. Mol Genet Metab. 2016 Dec;119(4):317-321. doi: 10.1016/j.ymgme.2016.10.009. Epub 2016 Oct 31. PubMed PMID: 27825584. 10: Panchaud A, Csajka C. Outbreak in meldonium positive laboratory tests: are we missing something? Br J Sports Med. 2016 Nov;50(22):1422-1423. doi: 10.1136/bjsports-2016-096253. Epub 2016 May 10. PubMed PMID: 27166287. 11: Jargin SV. Meldonium (Mildronate): Primum nоn nocere. Pharmacol Res. 2016 Dec;114:294. doi: 10.1016/j.phrs.2016.10.004. Epub 2016 Oct 8. PubMed PMID: 27725310. 12: Shchelochkov OA, Carrillo N, Venditti C. Propionic Acidemia. 2012 May 17 [updated 2016 Oct 6]. In: Adam MP, Ardinger HH, Pagon RA, Wallace SE, Bean LJH, Stephens K, Amemiya A, editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2018. Available from http://www.ncbi.nlm.nih.gov/books/NBK92946/ PubMed PMID: 22593918. 13: Waters PJ, Thuriot F, Clarke JT, Gravel S, Watkins D, Rosenblatt DS, Lévesque S. Methylmalonyl-coA epimerase deficiency: A new case, with an acute metabolic presentation and an intronic splicing mutation in the MCEE gene. Mol Genet Metab Rep. 2016 Sep 24;9:19-24. eCollection 2016 Dec. PubMed PMID: 27699154; PubMed Central PMCID: PMC5037260. 14: Bouitbir J, Haegler P, Singh F, Joerin L, Felser A, Duthaler U, Krähenbühl S. Impaired Exercise Performance and Skeletal Muscle Mitochondrial Function in Rats with Secondary Carnitine Deficiency. Front Physiol. 2016 Aug 10;7:345. doi: 10.3389/fphys.2016.00345. eCollection 2016. PubMed PMID: 27559315; PubMed Central PMCID: PMC4978712. 15: Schobersberger W, Dünnwald T, Gmeiner G, Blank C. Story behind meldonium-from pharmacology to performance enhancement: a narrative review. Br J Sports Med. 2017 Jan;51(1):22-25. doi: 10.1136/bjsports-2016-096357. Epub 2016 Jul 27. Review. PubMed PMID: 27465696. 16: Wambacq W, Rybachuk G, Jeusette I, Rochus K, Wuyts B, Fievez V, Nguyen P, Hesta M. Fermentable soluble fibres spare amino acids in healthy dogs fed a low-protein diet. BMC Vet Res. 2016 Jun 28;12(1):130. doi: 10.1186/s12917-016-0752-2. PubMed PMID: 27353524; PubMed Central PMCID: PMC4924337. 17: Arduini A, Zammit VA. A tennis lesson: sharp practice in the science behind the Sharapova case. Postgrad Med J. 2016 Aug;92(1090):429-30. doi: 10.1136/postgradmedj-2016-134124. Epub 2016 Jun 1. PubMed PMID: 27252310; PubMed Central PMCID: PMC4975811. 18: Higashimura Y, Naito Y, Takagi T, Uchiyama K, Mizushima K, Yoshikawa T. Propionate Promotes Fatty Acid Oxidation through the Up-Regulation of Peroxisome Proliferator-Activated Receptor α in Intestinal Epithelial Cells. J Nutr Sci Vitaminol (Tokyo). 2015;61(6):511-5. doi: 10.3177/jnsv.61.511. PubMed PMID: 26875495. 19: Dambrova M, Makrecka-Kuka M, Vilskersts R, Makarova E, Kuka J, Liepinsh E. Pharmacological effects of meldonium: Biochemical mechanisms and biomarkers of cardiometabolic activity. Pharmacol Res. 2016 Nov;113(Pt B):771-780. doi: 10.1016/j.phrs.2016.01.019. Epub 2016 Feb 2. Review. PubMed PMID: 26850121. 20: Berge RK, Bjørndal B, Strand E, Bohov P, Lindquist C, Nordrehaug JE, Svardal A, Skorve J, Nygård O. Tetradecylthiopropionic acid induces hepatic mitochondrial dysfunction and steatosis, accompanied by increased plasma homocysteine in mice. Lipids Health Dis. 2016 Feb 5;15:24. doi: 10.1186/s12944-016-0192-9. PubMed PMID: 26846427; PubMed Central PMCID: PMC4743328.