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07439

Sigma-Aldrich

Hexanoyl-L-carnitine

≥97.0% (TLC)

Synonym(s):

(2R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexyl)oxy]-1-propanaminium inner salt, (R)-Caproylcarnitine, n-Hexanoyl-L-carnitine, C6-Carnitine

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About This Item

Empirical Formula (Hill Notation):
C13H25NO4
CAS Number:
22671-29-0
Molecular Weight:
259.34
UNSPSC Code:
12352200
PubChem Substance ID:
329748440
NACRES:
NA.26

Quality Level

100

assay

≥97.0% (TLC)

optical activity

[α]/D -21±2°, c = 1 in H2O

impurities

≤10% water

format

neat

storage temp.

2-8°C

SMILES string

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

InChI

1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/t11-/m1/s1

InChI key

VVPRQWTYSNDTEA-LLVKDONJSA-N

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Biochem/physiol Actions

Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired re-absorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D H Chace et al.
Clinical chemistry, 43(11), 2106-2113 (1997-11-20)
We report the application of tandem mass spectrometry to prospective newborn screening for medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. MCAD deficiency is diagnosed from dried blood spots on filter paper cards from newborns on the basis of the increase of medium
Min Jung Kim et al.
Journal of obesity, 2013, 874981-874981 (2013-07-19)
The present study aimed to identify key metabolites related to weight reduction in humans by studying the metabolic profiles of sera obtained from 34 participants who underwent dietary intervention with black soybean peptides (BSP) for 12 weeks. This research is
P E Minkler et al.
Journal of chromatography, 613(2), 203-221 (1993-04-02)
This paper describes the development of a high-performance liquid chromatographic method for the quantitation of free carnitine, total carnitine, acetylcarnitine, propionylcarnitine, isovalerylcarnitine, hexanoylcarnitine and octanoylcarnitine in human urine. Carnitine and acylcarnitines were isolated from 10 or 25 microliters of urine
G Pierre et al.
Journal of inherited metabolic disease, 30(5), 815-815 (2007-05-18)
Carnitine-acylcarnitine translocase (CACT) deficiency is a rare disorder that results in long-chain fatty acids being unavailable for mitochondrial beta-oxidation and ketogenesis. It can present in the neonatal period or infancy with a severe clinical form, typically with convulsions, hypothermia, encephalopathy
E Schmidt-Sommerfeld et al.
The Journal of pediatrics, 115(4), 577-582 (1989-10-01)
Urinary carnitine esters were quantitated in an infant with medium-chain acylcoenzyme A dehydrogenase deficiency by means of a highly sensitive and specific radioisotopic exchange high-pressure liquid chromatography method. During fasting, the excretion of free carnitine and of acetylcarnitine, octanoylcarnitine, and

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