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CAS 552-63-6 Tropane Alkaloid Intermediate Tropane Alkaloid Intermediate High Purity GMP Grade

Tropic Acid

IUPAC: 3-Hydroxy-2-phenylpropanoic acid View on PubChem
CAS NUMBER
552-63-6
MOL. FORMULA
C9H10O3
MOL. WEIGHT
166.17 g/mol
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Scientific Overview

Tropic acid's structure --- a phenyl-substituted 3-hydroxypropanoic acid --- provides the ester-forming acid component that combines with tropine (the amino alcohol) to form atropine and related anticholinergic alkaloids via esterification. Its hydroxyl and carboxylic acid functional groups also make it a versatile substrate for esterification reactions, multistep depsipeptide synthesis, and isocoumarin derivative preparation in synthetic organic chemistry.

Tropic acid (DL form) is a phenylpropanoic acid derivative best known as the key synthetic building block for the tropane alkaloids atropine, hyoscyamine, and their derivatives. It also serves as a recognized pharmacopeial impurity marker (Ipratropium/Atropine EP Impurity C) in anticholinergic drug quality control.

Full Technical Data
Chemical Name Tropic Acid (DL-Tropic Acid)
CAS Number 552-63-6
IUPAC Name 3-Hydroxy-2-phenylpropanoic acid
Molecular Formula C9H10O3
Molecular Weight 166.17 g/mol g/mol
Reaction Scheme
Malonic Acid (or Phenylacetaldehyde derivative)
NA
NA
Tropic Acid
NA
Commercial Applications

Tropane Alkaloid Synthesis

Key esterification component in the synthesis of atropine, hyoscyamine, and anisodine.

Pharmacopeial Reference Standard

Used as an EP/USP-designated impurity reference for atropine and ipratropium bromide quality control.

Organic Synthesis Building Block

Substrate for esterification reactions and multistep synthesis of cyclic pentadepsipeptides.

Anticholinergic Drug Manufacturing

Intermediate supporting API production for anticholinergic and antispasmodic pharmaceuticals.

Market Therapeutic Focus
TROPANE ALKALOID INTERMEDIATE PHARMACEUTICAL MANUFACTURING ANTICHOLINERGIC / ANTISPASMODIC THERAPEUTICS ANALYTICAL REFERENCE STANDARDS ORGANIC SYNTHESIS INTERMEDIATES CRO/CDMO
Scientific Literature

Biosynthesis of Tropane Alkaloids: The Role of Tropic Acid

Authors: Robins, R.J. et al.

Phytochemistry

DOI: 10.1016/0031-9422(94)85015-4

Synthesis and Applications of Tropic Acid Derivatives

Authors: Rassu, G. et al.

Tetrahedron

DOI: 10.1016/j.tet.2009.09.001

Determination of Tropane Alkaloid Impurities in Anticholinergic Drug Products

Authors: Chen, Y. et al.

J. Pharm. Biomed. Anal.

DOI: 10.1016/j.jpba.2012.03.021
Peer Queries & FAQs
Why is tropic acid important in atropine synthesis?
It provides the carboxylic acid component that esterifies with tropine to form the atropine molecule, making it an essential synthetic intermediate for this anticholinergic drug class.
What is the significance of tropic acid as an impurity standard?
Since it's a direct precursor/degradation-related compound of atropine and ipratropium, pharmacopeias designate it as a named impurity (EP Impurity C) that must be controlled and quantified in finished drug products.
Is the DL (racemic) form used industrially, or is a specific enantiomer required?
Natural tropane alkaloids like atropine use the racemic tropic acid ester form (this is actually part of why atropine itself is the racemate of hyoscyamine); CAS 552-63-6 refers to this DL/racemic form.
What is the recommended storage condition?
Store in a tightly sealed container at 10--25°C (room temperature), protected from moisture and light.

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