Tropic acid

Last updated
Tropic acid
Phenylhydracrylic acid.svg
Names
Preferred IUPAC name
3-Hydroxy-2-phenylpropanoic acid
Other names
2-Phenylhydracrylic acid; Tropate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.201 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-020-6
KEGG
MeSH C011377
PubChem CID
UNII
  • InChI=1S/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12) Yes check.svgY
    Key: JACRWUWPXAESPB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
    Key: JACRWUWPXAESPB-UHFFFAOYAV
  • C1=CC=C(C=C1)C(CO)C(=O)O
Properties
C9H10O3
Molar mass 166.176 g·mol−1
Melting point 116 °C (241 °F; 389 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tropic acid is a chemical with IUPAC name 3-hydroxy-2-phenylpropanoic acid and condensed structural formula HOCH2CHPhCOOH. It is a laboratory reagent used in the chemical synthesis of atropine and hyoscyamine. Tropic acid is a chiral substance, existing as either a racemic mixture or as a single enantiomer.

Contents

Synthesis

Tropic acid can be prepared by the Ivanov reaction between phenylacetic acid and formaldehyde. In this method, the dianion of the acid is formed using a Grignard reagent, isopropyl magnesium chloride, and this reacts with the aldehyde to form the magnesium salt of the product, from which the pure acid is obtained after acidification with sulfuric acid. [1]

Many other methods have been used to make tropic acid, for example starting from acetophenone (1). [2]

Tropicacidsynthesis1.svg

Uses

Tropic acid is used in the chemical synthesis of atropine and hyoscyamine. [1]

Related Research Articles

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<span class="mw-page-title-main">Atropine</span> Anticholinergic medication used as antidote for nerve agent poisoning

Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.

<span class="mw-page-title-main">Hyoscyamine</span> Tropane alkaloid

Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

<span class="mw-page-title-main">Grignard reaction</span> Organometallic coupling reaction

The Grignard reaction is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides are added to the carbonyl groups of either an aldehyde or ketone under anhydrous conditions. This reaction is important for the formation of carbon–carbon bonds.

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<span class="mw-page-title-main">Bartoli indole synthesis</span> Chemical reaction

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<span class="mw-page-title-main">Ivanov reaction</span> Chemical reaction

The Ivanov reaction is the chemical reaction of the dianions (endiolates) of aryl acetic acids with electrophiles, primarily carbonyl compounds or isocyanates. The reaction was named after the Bulgarian organic chemist, Academician Dimitar Ivanov, who discovered it.

<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

Grignard reagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

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<span class="mw-page-title-main">Rieke metal</span> Group specially prepared, highly reactive metal powder

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<span class="mw-page-title-main">Magnesium acetate</span> Chemical compound

Anhydrous magnesium acetate has the chemical formula Mg(C2H3O2)2 and in its hydrated form, magnesium acetate tetrahydrate, it has the chemical formula Mg(CH3COO)2 • 4H2O. In this compound magnesium has an oxidation state of 2+. Magnesium acetate is the magnesium salt of acetic acid. It is deliquescent and upon heating, it decomposes to form magnesium oxide. Magnesium acetate is commonly used as a source of magnesium in biological reactions.

<span class="mw-page-title-main">Phenylsodium</span> Chemical compound

Phenylsodium C6H5Na is an organosodium compound. Solid phenylsodium was first isolated by Nef in 1903. Although the behavior of phenylsodium and phenyl magnesium bromide are similar, the organosodium compound is very rarely used.

<span class="mw-page-title-main">Apoatropine</span> Chemical compound

Apoatropine (atropatropine) is a member of class of tropane alkaloids. Chemically, it is an ester formed from tropine and atropic acid. Apoatropine can be found in plants of family Solanaceae. It is a bitter crystalline alkaloid. Examples of related tropane alkaloids include atropine, hyoscyamine, and hyoscine. Though apoatropine is found in various plants, it can also be prepared by the dehydration of atropine using nitric acid. Apoatropine is used as a pigment.

References

  1. 1 2 Blicke, F. F.; Raffelson, Harold; Barna, Bohdan (1952). "The Preparation of Tropic Acid". Journal of the American Chemical Society. 74: 253. doi: 10.1021/ja01121a504 .
  2. Gadzikowska, M; Grynkiewicz, G (2002). "Tropane alkaloids in pharmaceutical and phytochemical analysis". Acta Poloniae Pharmaceutica. 59 (2): 149–60. PMID   12365608.