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Merck

08984

Butyryl-L-carnitine

analytical standard

Synonym(s):

(2R)-3-Carboxy-N,N,N-trimethyl-2-(1-oxobutoxy)-1-propanaminium inner salt, Butanoyl-L-carnitine, C4-Carnitine

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About This Item

Empirical Formula (Hill Notation):
C11H21NO4
CAS Number:
25576-40-3
Molecular Weight:
231.29
UNSPSC Code:
41116107
NACRES:
NB.21
MDL number:
MFCD01674827

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InChI

1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1

SMILES string

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

InChI key

QWYFHHGCZUCMBN-SECBINFHSA-N

grade

analytical standard

assay

≥97.0% (HPLC)

optical activity

[α]/D -23.0±2.0°, c = 0.1 in H2O

shelf life

limited shelf life, expiry date on the label

impurities

≤10.0% water

application(s)

clinical testing

format

neat

storage temp.

2-8°C

Quality Level

100

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Application

Butyryl-L-carnitine may be used as an analytical reference standard for the separation and identification of underivatized butyryl-L-carnitine in human plasma samples using high-performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS). It may also be used as an analytical reference standard for the quantification of the analyte in biological samples using chromatography-based techniques.

General description

Butyryl-L-carnitine is a naturally occurring compound belonging to the acylcarnitine class of compounds as listed in the human metabolome database (HMBD). These compounds are reported to be used as biomarkers in the diagnosis of carnitine deficiency. It acts as a carrier of long chain acyl groups from activated fatty acids across the inner mitochondrial membrane into the mitochondrial matrix where they undergo β-oxidation to acetyl CoA to obtain usable energy via the citric acid cycle.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6802
BCCM5856
BCCL6165
BCCH5805
BCCG8051

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Tracing and separating plasma components causing matrix effects in hydrophilic interaction chromatography?electrospray ionization mass spectrometry
Journal of Chromatography. B, Biomedical Sciences and Applications, 923, 83-91 (2013)
Separation and identification of underivatized plasma acylcarnitine isomers using liquid chromatography?tandem mass spectrometry for the differential diagnosis of organic acidemias and fatty acid oxidation defects
Peng M, et al.
Journal of Chromatography A, 1319, 97-106 (2016)
Metabolomic analyses reveal extensive progenitor cell deficiencies in a mouse model of duchenne muscular dystrophy
Joseph J, et al.
Metabolites, 8(4), 61-61 (2018)
Exogenous carnitine application augments transport of fatty acids into mitochondria and stimulates mitochondrial respiration in maize seedlings grown under normal and cold conditions
Turk H, et al.
Cryobiology, 9, 97-103 (2019)
Ralph Fingerhut et al.
Analytical chemistry, 81(9), 3571-3575 (2009-03-28)
Electrospray ionization-tandem mass spectrometry (ESI-MS/MS) is increasingly used in newborn screening programs. Acylcarnitine profiles from dried blood spots (DBS) are used to detect fatty acid oxidation disorders, carnitine cycle disorders, and organic acidurias. Stored dried blood is also a valuable
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