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Merck

63978

Supelco

(RS)-(Methylenecyclopropyl)acetic acid

analytical standard

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About This Item

Fórmula empírica (notación de Hill):
C6H8O2
Número de CAS:
Peso molecular:
112.13
Beilstein:
1927126
Número MDL:
Código UNSPSC:
85151701
ID de la sustancia en PubChem:
NACRES:
NA.24

grado

analytical standard

Nivel de calidad

Ensayo

≥95.0% (HPLC)

caducidad

limited shelf life, expiry date on the label

técnicas

HPLC: suitable
gas chromatography (GC): suitable

aplicaciones

food and beverages

Formato

neat

temp. de almacenamiento

−20°C

cadena SMILES

OC(=O)CC1CC1=C

InChI

1S/C6H8O2/c1-4-2-5(4)3-6(7)8/h5H,1-3H2,(H,7,8)

Clave InChI

QJBXAEKEXKLLLZ-UHFFFAOYSA-N

Aplicación

(RS)-(Methylenecyclopropyl)acetic acid (MCPA), an inhibitor of multiple acyl-CoA dehydrogenase enzymes, is derived from hypoglycin A metabolism. MCPA forms non-metabolizable carnitine and coenzyme A (CoA) esters thereby depressing tissue levels of these cofactors and making them less available for other biochemical reactions. (RS)-(Methylenecyclopropyl)acetic acid may be used as a reference material during the analysis of MCPA.
Hypoglycin A is metabolized by means of transamination and oxidative decarboxylation to methylene cyclopropyl acetic acid (MCPA). MCPA forms nonmetabolizable carnitine and coenzyme A (CoA) esters, thereby depressing tissue levels of these cofactors and making them less available for other biochemical reactions.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

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Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral - Skin Irrit. 2

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Certificados de análisis (COA)

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Visite la Librería de documentos

Hypoglycin and metabolically related inhibitors.
D Billington et al.
Methods in enzymology, 72, 610-616 (1981-01-01)
Y K Lieu et al.
The American journal of physiology, 272(3 Pt 1), E359-E366 (1997-03-01)
To examine the changes in coenzyme A profile and the possible corrective effects of carnitine supplementation in the genetic disorders of mitochondrial beta-oxidation, we carried out experiments using an inhibitor of multiple acyl-CoA dehydrogenase enzymes, methylenecyclopropaneacetic acid (MCPA), in rat
David Grünig et al.
Biochemical pharmacology, 177, 113860-113860 (2020-03-14)
Treatment with valproate is associated with hepatic steatosis, but the mechanisms are not fully elucidated in human cell systems. We therefore investigated the effects of valproate on fatty acid and triglyceride metabolism in HepaRG cells, a human hepatoma cell line.
The antagonism of the toxicity of hypoglycin by glycine.
S S Al-Bassam et al.
Biochemical pharmacology, 30(20), 2817-2824 (1981-10-01)
K Y Tserng et al.
Biochemistry, 30(44), 10755-10760 (1991-11-05)
To study the structure-activity relationship between pentanoic acid analogues and the inhibition of fatty acid oxidation, a number of 4-pentenoic and methylenecyclopropaneacetic acid derivatives were prepared. All compounds inhibited palmitoylcarnitine oxidation in rat liver mitochondria, with 50% inhibition occurring at

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