Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

63978

Supelco

(RS)-(Methylenecyclopropyl)acetic acid

analytical standard

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C6H8O2
CAS Number:
1073-00-3
Molecular Weight:
112.13
Beilstein:
1927126
MDL number:
MFCD11558999
UNSPSC Code:
85151701
PubChem Substance ID:
329759918
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

storage temp.

−20°C

SMILES string

OC(=O)CC1CC1=C

InChI

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

InChI key

QJBXAEKEXKLLLZ-UHFFFAOYSA-N

Application

(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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

63978-BULK:
63978-VAR:
63978-100MG:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCG4641
BCCB8936
BCBW1394
BCBR6642V
BCBM8228V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
Methylenecyclopropaneacetic acid, a metabolite of hypoglycin.
C Von Holt
Biochimica et biophysica acta, 125(1), 1-10 (1966-08-03)
The antagonism of the toxicity of hypoglycin by glycine.
S S Al-Bassam et al.
Biochemical pharmacology, 30(20), 2817-2824 (1981-10-01)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service