Lauroylcarnitine | CAS#25518-54-1 | acylcarnitine

MedKoo Cat#: 596948 | Name: Lauroylcarnitine

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Description:

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

Lauroylcarnitine is a long-chain acylcarnitine formed by the esterification of lauric acid (a 12-carbon saturated fatty acid) with L-carnitine. It plays a role in fatty acid metabolism by facilitating the transport of medium- to long-chain fatty acids into mitochondria for β-oxidation. Lauroylcarnitine is also studied as a biomarker for metabolic disorders and mitochondrial dysfunction, particularly in contexts involving altered lipid utilization.

Chemical Structure

Lauroylcarnitine

CAS#25518-54-1

Theoretical Analysis

MedKoo Cat#: 596948

Name: Lauroylcarnitine

CAS#: 25518-54-1

Chemical Formula: C19H37NO4

Exact Mass: 343.2723

Molecular Weight: 343.51

Elemental Analysis: C, 66.43; H, 10.86; N, 4.08; O, 18.63

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 310.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Synonym

Lauroylcarnitine; Dodecanoyl-L-carnitine; L-Carnitine dodecanoyl ester; (R)-Dodecanoylcarnitine;

IUPAC/Chemical Name

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

InChi Key

FUJLYHJROOYKRA-QGZVFWFLSA-N

InChi Code

InChI=1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/t17-/m1/s1

SMILES Code

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

Appearance

Solid powder

Purity

>95% (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:

Dodecanoylcarnitine is present in fatty acid oxidation disorders such as long-chain acyl CoA dehydrogenase deficiency, carnitine palmitoyltransferase I/II deficiency, and is also associated with celiac disease.

In vitro activity:

Lauroylcarnitine and palmitoylcarnitine increased influx and decreased efflux of these substrates, in a manner dependent on their concentration and acyl chain lengths by increasing influx and inhibiting efflux of the substrates. Reference: Eur J Drug Metab Pharmacokinet. 2010 Sep;35(1-2):1-7. https://pubmed.ncbi.nlm.nih.gov/21495260/

In vivo activity:

This study examined the effect of acylcarnitines on the in situ bioavailability of lucifer yellow (LY) from the loops of small and large intestines of rats. The area under the blood concentration of LY versus time curve (AUC) from the jejunum was significantly increased by the treatments of the loop with 100 µM lauroylcarnitine (LC) or 100 µM palmitoylcarnitine (PC) (fourfold and 17-fold, respectively). Reference: J Pharm Sci. 2012 Sep;101(9):3511-7. https://pubmed.ncbi.nlm.nih.gov/22678774/

	Solvent	mg/mL	mM
Solubility
	DMSO	33.3	97.03

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 343.51 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. Tomita M, Doi N, Hayashi M. Effects of acylcarnitines on efflux transporting system in Caco-2 cell monolayers. Eur J Drug Metab Pharmacokinet. 2010 Sep;35(1-2):1-7. doi: 10.1007/s13318-010-0001-1. PMID: 21495260. 2. Doi N, Tomita M, Hayashi M. Absorption enhancement effect of acylcarnitines through changes in tight junction protein in Caco-2 cell monolayers. Drug Metab Pharmacokinet. 2011;26(2):162-70. doi: 10.2133/dmpk.dmpk-10-rg-071. Epub 2010 Dec 27. PMID: 21206134. 3. Tomita M, Doi N, Kimura A, Hayashi M. Increases in bioavailability of poorly absorbed drug by acylcarnitine. J Pharm Sci. 2012 Sep;101(9):3511-7. doi: 10.1002/jps.23214. Epub 2012 Jun 7. PMID: 22678774. 4. Moyes CD, Buck LT, Hochachka PW. Temperature effects on pH of mitochondria isolated from carp red muscle. Am J Physiol. 1988 Apr;254(4 Pt 2):R611-5. doi: 10.1152/ajpregu.1988.254.4.R611. PMID: 3354709.

In vitro protocol:

In vivo protocol:

1. Tomita M, Doi N, Kimura A, Hayashi M. Increases in bioavailability of poorly absorbed drug by acylcarnitine. J Pharm Sci. 2012 Sep;101(9):3511-7. doi: 10.1002/jps.23214. Epub 2012 Jun 7. PMID: 22678774. 2. Moyes CD, Buck LT, Hochachka PW. Temperature effects on pH of mitochondria isolated from carp red muscle. Am J Physiol. 1988 Apr;254(4 Pt 2):R611-5. doi: 10.1152/ajpregu.1988.254.4.R611. PMID: 3354709.

1: Danielsen EM, Hansen GH. Intestinal surfactant permeation enhancers and their interaction with enterocyte cell membranes in a mucosal explant system. Tissue Barriers. 2017 Jul 3;5(3):e1361900. doi: 10.1080/21688370.2017.1361900. PubMed PMID: 28837408; PubMed Central PMCID: PMC5571779. 2: Schoonen JW, van Duinen V, Oedit A, Vulto P, Hankemeier T, Lindenburg PW. Continuous-flow microelectroextraction for enrichment of low abundant compounds. Anal Chem. 2014 Aug 19;86(16):8048-56. doi: 10.1021/ac500707v. Epub 2014 Jun 19. PubMed PMID: 24892382. 3: Chen L, Fan J, Li Y, Shi X, Ju D, Yan Q, Yan X, Han L, Zhu H. Modified Jiu Wei Qiang Huo decoction improves dysfunctional metabolomics in influenza A pneumonia-infected mice. Biomed Chromatogr. 2014 Apr;28(4):468-74. doi: 10.1002/bmc.3055. Epub 2013 Oct 17. PubMed PMID: 24132661. 4: Peng M, Liu L, Jiang M, Liang C, Zhao X, Cai Y, Sheng H, Ou Z, Luo H. Measurement of free carnitine and acylcarnitines in plasma by HILIC-ESI-MS/MS without derivatization. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Aug 1;932:12-8. doi: 10.1016/j.jchromb.2013.05.028. Epub 2013 Jun 2. PubMed PMID: 23816563. 5: Sampey BP, Freemerman AJ, Zhang J, Kuan PF, Galanko JA, O'Connell TM, Ilkayeva OR, Muehlbauer MJ, Stevens RD, Newgard CB, Brauer HA, Troester MA, Makowski L. Metabolomic profiling reveals mitochondrial-derived lipid biomarkers that drive obesity-associated inflammation. PLoS One. 2012;7(6):e38812. doi: 10.1371/journal.pone.0038812. Epub 2012 Jun 12. PubMed PMID: 22701716; PubMed Central PMCID: PMC3373493. 6: Tomita M, Doi N, Kimura A, Hayashi M. Increases in bioavailability of poorly absorbed drug by acylcarnitine. J Pharm Sci. 2012 Sep;101(9):3511-7. doi: 10.1002/jps.23214. Epub 2012 Jun 7. PubMed PMID: 22678774. 7: Tomita M, Doi N, Hayashi M. Effects of acylcarnitines on efflux transporting system in Caco-2 cell monolayers. Eur J Drug Metab Pharmacokinet. 2010 Sep;35(1-2):1-7. PubMed PMID: 21495260. 8: Doi N, Tomita M, Hayashi M. Absorption enhancement effect of acylcarnitines through changes in tight junction protein in Caco-2 cell monolayers. Drug Metab Pharmacokinet. 2011;26(2):162-70. Epub 2010 Dec 27. PubMed PMID: 21206134. 9: Bene J, Komlósi K, Gasztonyi B, Juhász M, Tulassay Z, Melegh B. Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. PubMed PMID: 16425363; PubMed Central PMCID: PMC4355763. 10: Eder K, Felgner J, Becker K, Kluge H. Free and total carnitine concentrations in pig plasma after oral ingestion of various L-carnitine compounds. Int J Vitam Nutr Res. 2005 Jan;75(1):3-9. PubMed PMID: 15830915. 11: Dufes C, Olivier JC, Gaillard F, Gaillard A, Couet W, Muller JM. Brain delivery of vasoactive intestinal peptide (VIP) following nasal administration to rats. Int J Pharm. 2003 Apr 14;255(1-2):87-97. PubMed PMID: 12672605. 12: Kamimori H, Konishi M. Evaluation and application of liquid chromatographic columns coated with 'intelligent' ligands: (I) acylcarnitine column. J Chromatogr A. 2001 Sep 21;929(1-2):1-12. PubMed PMID: 11594390. 13: Hayashi M, Sakai T, Hasegawa Y, Nishikawahara T, Tomioka H, Iida A, Shimizu N, Tomita M, Awazu S. Physiological mechanism for enhancement of paracellular drug transport. J Control Release. 1999 Nov 1;62(1-2):141-8. PubMed PMID: 10518645. 14: Kagatani S, Inaba N, Fukui M, Sonobe T. Nasal absorption kinetic behavior of azetirelin and its enhancement by acylcarnitines in rats. Pharm Res. 1998 Jan;15(1):77-81. PubMed PMID: 9487550. 15: Kagatani S, Shinoda T, Fukui M, Ohmura T, Hasumi S, Sonobe T. Enhancement of nasal salmon calcitonin absorption by lauroylcarnitine chloride in rats. Pharm Res. 1996 May;13(5):739-43. PubMed PMID: 8860430. 16: McCallum CD, Epand RM. Insulin receptor autophosphorylation and signaling is altered by modulation of membrane physical properties. Biochemistry. 1995 Feb 14;34(6):1815-24. PubMed PMID: 7849042. 17: Moyes CD, Buck LT, Hochachka PW. Temperature effects on pH of mitochondria isolated from carp red muscle. Am J Physiol. 1988 Apr;254(4 Pt 2):R611-5. PubMed PMID: 3354709. 18: Haeyaert P, Verdonck A, Van Cauwelaert FH. Influence of acylcarnitines of different chain length on pure and mixed phospholipid vesicles and on sarcoplasmic reticulum vesicles. Chem Phys Lipids. 1987 Oct;45(1):49-63. PubMed PMID: 2965625. 19: Mentlein R. The tumor promoter 12-O-tetradecanoyl phorbol 13-acetate and regulatory diacylglycerols are substrates for the same carboxylesterase. J Biol Chem. 1986 Jun 15;261(17):7816-8. PubMed PMID: 3711110.