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Methylene cyclopropyl acetic acid information


Methylene cyclopropyl acetic acid
Names
IUPAC name
2-(2-methylidenecyclopropyl)acetic acid
Other names
MCPA; Methylenecyclopropaneacetic acid
Identifiers
CAS Number
  • 1073-00-3 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL314481 checkY
ChemSpider
  • 8389873 checkY
ECHA InfoCard 100.189.911 Edit this at Wikidata
PubChem CID
  • 10214381
UNII
  • 516144FI4M checkY
CompTox Dashboard (EPA)
  • DTXSID30910284 Edit this at Wikidata
InChI
  • InChI=1S/C6H8O2/c1-4-2-5(4)3-6(7)8/h5H,1-3H2,(H,7,8) checkY
    Key: QJBXAEKEXKLLLZ-UHFFFAOYSA-N checkY
SMILES
  • OC(=O)CC1CC1=C
Properties
Chemical formula
C6H8O2
Molar mass 112.128 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methylene cyclopropyl acetic acid (MCPA) is found in lychee seeds and also a toxic metabolite in mammalian digestion after eating hypoglycin, present in the unripe ackee fruit, grown in Jamaica and in Africa. By blocking coenzyme A and carnitine, MPCA causes a decrease in β-oxidation of fatty acids, and hence gluconeogenesis.

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Methylene cyclopropyl acetic acid

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Methylene cyclopropyl acetic acid (MCPA) is found in lychee seeds and also a toxic metabolite in mammalian digestion after eating hypoglycin, present...

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Carboxylic acid

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-ic acid and -ate for a conjugate acid and its conjugate base, respectively. For example, the conjugate base of acetic acid is acetate. Carbonic acid, which...

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Organic acid anhydride

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word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride. Mixed (or unsymmetrical) acid anhydrides...

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Carbanion

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to be acids (e.g., mineral acids like nitric acid, or carboxylic acids like acetic acid), carbon acids are typically many orders of magnitude weaker...

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Jamaican vomiting sickness

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medical school in Grenada.[citation needed] Reye syndrome Methylene cyclopropyl acetic acid Gordon, André (2015-01-01), Gordon, André (ed.), "Chapter...

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Ester

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oxoacids (e.g. esters of acetic acid, carbonic acid, sulfuric acid, phosphoric acid, nitric acid, xanthic acid), but also from acids that do not contain oxygen...

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Sulfonic acid

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p-Toluenesulfonic acid and methanesulfonic acid have pKa values of −2.8 and −1.9, respectively, while those of benzoic acid and acetic acid are 4.20 and 4...

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Amide

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the term "amide" to the stem of the parent acid's name. For instance, the amide derived from acetic acid is named acetamide (CH3CONH2). IUPAC recommends...

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Phosphonate

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Vinylphosphonic acid can be prepared by the reaction of PCl3 and acetaldehyde: PCl3 + CH3CHO → CH3CH(O−)PCl+ 3 This adduct reacts with acetic acid: CH3CH(O−)PCl+...

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Methyl group

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to produce optically pure methyl compounds, e.g., chiral acetic acid (deuterotritoacetic acid CHDTCO2H). Through the use of chiral methyl groups, the stereochemical...

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C6H8O2

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4-Cyclohexanedione Cyclotene (maple lactone) Methylene cyclopropyl acetic acid Parasorbic acid Sorbic acid This set index page lists chemical structure...

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Benzyl group

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(CrO3−dmpyz) will selectively oxidize a benzylic methylene group to a carbonyl: (ArCH2R → ArC(O)R). 2-iodoxybenzoic acid in DMSO performs similarly. Benzyl groups...

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2019 Bihar encephalitis outbreak

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in India. A 2014 study published in Lancet found that the methylene cyclopropyl acetic acid and hypoglycin A found in unripe lychee (Litchi chinensis)...

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Aldehyde

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potassium permanganate, nitric acid, chromium(VI) oxide, and chromic acid. The combination of manganese dioxide, cyanide, acetic acid and methanol will convert...

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Acetyl group

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including acetic acid, the neurotransmitter acetylcholine, acetyl-CoA, acetylcysteine, acetaminophen (also known as paracetamol), and acetylsalicylic acid (also...

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Thiocarboxylic acid

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For thioacetic acid the pKa is near 3.4 vs 4.72 for acetic acid. The conjugate base of thioacetic acid, thioacetate is reagents for installing thiol groups...

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Functional group

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a single multiple bond. For example, a methylene bridge (methanediyl) has two single bonds, whereas a methylene group (methylidene) has one double bond...

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Nitro compound

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Oxidation of Oximes to Nitro Compounds with Sodium Perborate in Glacial Acetic Acid". Synlett. 1992 (4): 337–339. doi:10.1055/s-1992-22006. Ehud, Keinan;...

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Oxime

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acid. and a similar reaction with propiophenone, the reaction of phenacyl chloride, the reaction of malononitrile with sodium nitrite in acetic acid A...

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Acyl group

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groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached...

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Acetoxy group

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ester form of acetic acid, such as a N-hydroxysuccinimide ester, although this is not advisable due to higher costs and difficulties. Acetic anhydride in...

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Vinyl group

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Liebig to "acetyl", because he believed it to be the radical of the acetic acid. The modern term was coined by German chemist Hermann Kolbe in 1851,...

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Benzene

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acidic material was derived from benzoin by sublimation, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus...

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Sulfoxide

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CH3S(O)CH2Na + H2 In the Pummerer rearrangement, alkyl sulfoxides react with acetic anhydride to give migration of the oxygen from sulfur to the adjacent carbon...

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Ethylene

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reaction) of ethylene results in propionaldehyde, a precursor to propionic acid and n-propyl alcohol. Ethylene has long represented the major nonfermentative...

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Melengestrol

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tetrasubstituted oxirane ring in acid proceeds with loss of a proton from the β position (16 methyl) (9) to afford the desired 16-methylene-17α-hydroxy-20-ketone...

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Controlled Drugs and Substances Act

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Class A Precursors Acetic anhydride N-Acetylanthranilic acid (2-acetamidobenzoic acid) and its salts Anthranilic acid (2-aminobenzoic acid) and its salts...

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Methoxy group

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groups Hydrocarbons (only C and H) Alkyl Methyl Ethyl Propyl Cyclopropyl Butyl Pentyl Methylene Bridge Methine Alkene Vinyl Allyl 1-Propenyl Crotyl Allene...

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Nitrene

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nitrene intermediate is suspected in this C–H insertion involving an oxime, acetic anhydride leading to an isoindole: Nitrene cycloaddition. With alkenes,...

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