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07439

Sigma-Aldrich

Hexanoyl-L-carnitine

≥97.0% (TLC)

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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
Empirical Formula (Hill Notation):
C13H25NO4
CAS Number:
Molecular Weight:
259.34
PubChem Substance ID:
NACRES:
NA.26

Quality Level

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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1 of 4

This Item
062060426508084
Hexanoyl-L-carnitine ≥97.0% (TLC)

07439

Hexanoyl-L-carnitine

Octanoyl-L-carnitine analytical standard

06206

Octanoyl-L-carnitine

Valeryl-L-carnitine analytical standard

04265

Valeryl-L-carnitine

Stearoyl-L-carnitine analytical standard

08084

Stearoyl-L-carnitine

format

neat

format

neat

format

neat

format

neat

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

optical activity

[α]/D -21±2°, c = 1 in H2O

optical activity

[α]/D -17±2°, c = 0.1 in H2O

optical activity

[α]/D -20.0±2.0°, c = 0.1 in H2O

optical activity

[α]/D -15.0±2.0°, c = 1 in methanol

impurities

≤10% water

impurities

≤10% water

impurities

≤10% water

impurities

≤10.0% water

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


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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
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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
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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