tropic acid
hydracrylic acid, 2-phenyl-
Identification
| Name | tropic acid |
| IUPAC | 3-hydroxy-2-phenylpropanoic acid |
| CAS Number | 552-63-6 |
| EINECS | 208-465-3 |
| FDA UNII | 9RM4U80765 |
| Molecular Formula | C9 H10 O3 |
| Molecular Weight | 166.17630000 |
| MDL Number | MFCD00004255 |
| Nikkaji Number | J6.688E |
| Beilstein | 2209199 |
| XlogP3 | 0.80 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 118.00 °C. @ 760.00 mm Hg |
| Boiling Point | 322.50 °C. @ 760.00 mm Hg (est) |
| Flash Point | 326.00 °F. TCC ( 163.10 °C. ) (est) |
| logP (o/w) | 0.280 (est) |
| Soluble in | water, 2.00E+04 mg/L @ 25 °C (exp) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for tropic acid usage levels up to | not for fragrance use. |
| Recommendation for tropic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
benzeneacetic acid, alpha-(hydroxymethyl)-
hydracrylic acid, 2-phenyl-
hydratropic acid, beta-hydroxy-
3-
hydroxy-2-phenylpropanoic acid
beta-
hydroxyhydratropic acid
alpha-(
hydroxymethyl) benzene acetic acid
(1)-(
hydroxymethyl) phenyl acetic acid
alpha-(
hydroxymethyl)-alpha-toluic acid
2-
phenyl hydracrylic acid
2-
phenylhydracrylic acid
alpha-
toluic acid, alpha-(hydroxymethyl)-
PubMed:
The effect of transdermal scopolamine for the prevention of postoperative nausea and vomiting.
PubMed:
Crystal structures of CbpF complexed with atropine and ipratropium reveal clues for the design of novel antimicrobials against Streptococcus pneumoniae.
PubMed:
Rapid resolution liquid chromatography for monitoring the quality of stockpiled atropine preparations for injection.
PubMed:
High-performance liquid-chromatographic tandem-mass spectrometric methods for atropinesterase-mediated enantioselective and chiral determination of R- and S-hyoscyamine in plasma.
PubMed:
Determination of hydroxyurea in serum or plasma using gas chromatography-mass spectrometry (GC-MS).
PubMed:
Occurrence and behavior of system peaks in RP HPLC with solely aqueous mobile phases.
PubMed:
Analysis of scopolamine and its eighteen metabolites in rat urine by liquid chromatography-tandem mass spectrometry.
PubMed:
Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants.
PubMed:
Liquid chromatography-electrospray ionization ion trap mass spectrometry for analysis of in vivo and in vitro metabolites of scopolamine in rats.
PubMed:
[Detection of anisodamine and its metabolites in rat feces by tandem mass spectrometry].
PubMed:
Impurity profiling of atropine sulfate by microemulsion electrokinetic chromatography.
PubMed:
The presence of atropinesterase activity in animal plasma.
PubMed:
Liquid chromatography-tandem mass spectrometry analysis of anisodamine and its phase I and II metabolites in rat urine.
PubMed:
Evaluation of diabetes-related short-chain organic acids in rat plasma by capillary electrophoresis.
PubMed:
Determination of L-hyoscyamine in atropine and D-hyoscyamine in L-hyoscyamine by chiral capillary electrophoresis as an alternative to polarimetry.
PubMed:
Analysis of tropane and related alkaloids.
PubMed:
The biosynthesis of shikimate metabolites.
PubMed:
The phenylacetyl-CoA catabolon: a complex catabolic unit with broad biotechnological applications.
PubMed:
[Chirality of natural products: hyoscyamine and scopolamine].
PubMed:
The separation of ipratropium bromide and its related compounds.
PubMed:
Determination of the main tropane alkaloids from transformed Hyoscyamus muticus plants by capillary zone electrophoresis.
PubMed:
1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidine (DNS-Apy) as a fluorescence chiral labelling reagent for carboxylic acid enantiomers.
PubMed:
Enzymology of oxidation of tropic acid to phenylacetic acid in metabolism of atropine by Pseudomonas sp. strain AT3.
PubMed:
GC-MS profiling of urinary organic acids evaluated as a quantitative method.
PubMed:
Atropine Metabolism by Pseudomonas sp. Strain AT3: Evidence for Nortropine as an Intermediate in Tropine Breakdown and Reactions Leading to Succinate.
PubMed:
Liquid chromatographic determination of atropine in nerve gas antidotes and other dosage forms.
PubMed:
Highly enantioselective capillary electrophoretic separations with dilute solutions of the macrocyclic antibiotic ristocetin A.
PubMed:
Simple high-performance liquid chromatographic method for assessing the deterioration of atropine-oxime mixtures employed as antidotes in the treatment of nerve agent poisoning.
PubMed:
The isolation and identification of 6-hydroxycyclohepta-1,4-dione as a novel intermediate in the bacterial degradation of atropine.
PubMed:
Tropane alkaloid production in Datura stramonium suspension cultures: elicitor and precursor effects.
PubMed:
Metabolism in vivo of the tropane alkaloid, scopolamine, in several mammalian species.
PubMed:
Determination of the enantiomeric purity of scopolamine isolated from plant extract using achiral/chiral coupled column chromatography.
PubMed:
A monoclonal antibody to scopolamine and its use for competitive enzyme-linked immunosorbent assay.
PubMed:
Recent developments in the biosynthesis of the tropane alkaloids.
PubMed:
Quantitative correlations and reexamination of the importance of hydrophobic and steric factors in anticholinergic drug receptor interactions.
PubMed:
Investigation by NMR spectroscopy of the interaction between synthetic soluble (-)-dopa melanin and drugs.
PubMed:
A competitive solid-phase enzyme immunoassay for the evaluation of tropane alkaloids in plant material, using anti-DL-tropic acid antibodies.
PubMed:
The metabolism of atropine in man.
PubMed:
Simultaneous determination of atropine sulphate and tropic acid by reversed phase high-pressure liquid chromatography.
PubMed:
[Vagus block in the therapy of bradycardial arrhythmias--the role of autonomic balance].
PubMed:
Structure-activity requirements for hypotension and alpha-adrenergic receptor blockade by analogues of atropine.
PubMed:
Binding of indomethacin ester with tropic acid to human serum albumin.
PubMed:
[Clinical evaluation of indomethacin esters with tropic acid in the treatment of progressive polyarthritis].
PubMed:
Pharmacokinetic evidence for possible renal accumulation of model organic anions in rats.
PubMed:
Radioimmunoassay for atropine and l-hyoscyamine.
PubMed:
[Photometric determination of indomethacin and its tropic acid ester (troposin)].
PubMed:
[Polarographic determination of indomethacin ester using tropic acid].
PubMed:
[Flurometry in pharmaceutical analysis. I. Flurometric determination of indomethacin and indomethacin ester with tropic acid].
PubMed:
Erythema multiforme and urticaria. Eruptions induced by chemically related ophthalmic anticholinergic agents.
PubMed:
The biosynthesis of tropic acid [proceedings].
PubMed:
High pressure liquid chromatographic determination of atropine sulfate and scopolamine hydrobromide in tablets.
PubMed:
C-NMR spectroscopy of tropane alkaloids.
PubMed:
Ion-pair high-performance liquid chromatographic method for the determination of atropine sulfate and tropic acid.
PubMed:
Rationale for apparent differences in pharmacokinetic aspects of model compounds determined from blood level data and urinary excretion data in rats.
PubMed:
Biosynthesis of tropic acid. I. Incorporation of cinnamic acid-2-14C in Datura innoxia.
PubMed:
[General pharmacology and secretion inhibitory action of (8r)-3alpha-hydroxy-8-isopropyl-1alphaH,5alphaH-tropanium bromide-(+/-)-tropate (ipratropiumbromide) (author's transl)].
PubMed:
[A new method for technical synthesis of tertiary and quaternary d,1-tropic acid esters of some N-subsituted nortropan- and granatan-3-oles (author's transl)].
PubMed:
Use of carbon-13 nuclear magnetic resonance to establish that the biosynthesis of tropic acid involves an intramolecular rearrangement of phenylalanine.
PubMed:
Mechanistic evaluation of modifications of distribution. Pharmacokinetic parameters of model organic anions in presence of a model renal tubular secretion inhibitor in rats.
PubMed:
[The action of a tropic acid ester on bronchospasm: a double-blind study (author's transl)].
PubMed:
[Double-blind study for the comparison of the broncholytic effect of a new tropic acid derivative with isoprenaline].
PubMed:
Biosynthesis of tropic acid in Datura innoxia root tissue.
PubMed:
[Preservation of atropine sulfate solutions. I. Demonstration of tropic acid by thin-layer chromatography].
PubMed:
The breakdown of tropic acid in Pseudomonas putida strain L. I. Utilization of various substrates; the conversion of tropic acid into phenylacetic acid.
PubMed:
Preparation and characterization of the tropic acid esters of tropan-3-beta-ol, granatan-3-alpha-ol and granatan-3-beta-ol.
PubMed:
Enzymic assay of tropic acid esters.
PubMed:
Kinetics of urinary excretion of D-(minus)-mandelic acid and its homologs. II. Competitive inhibitory effect of D-(minus)-mandelic acid and DL-tropic acid on their renal tubular secretion in rats.
PubMed:
[Study of the racemisation, hydrolysis and other degradation reactions of some tropic acid esters and noradrenaline in aqueous solutions. II].
PubMed:
[Study of the racemisation, hydrolysis and other degradation reactions of some tropic acid esters and noradrenaline in aqueous solutions. I].
PubMed:
[Clinical study on the effect of tropic acid amide on the visual acuity and refraction in myopic children. 8].
PubMed:
Non-enzymic transformation of phenylalanine to tropic acid.
PubMed:
Biosynthesis of tropic acid in Datura innoxia.
PubMed:
Group therapy with tropic acid amide (Mydrin M) against pseudo-myopia in primary school children.
PubMed:
[Clinical study of the effect of tropic acid amide on the visual acuity and refraction in myopic children. VII].
PubMed:
Synthesis of tropine-labeled atropine. I. Micro methods for the synthesis of tropine and for its esterification with tropic acid.
PubMed:
[ON THE RESULT OF MASS TREATMENT OF MYOPIC CHILDREN WITH TROPIC ACID N-ETHYL-N-(GAMMA-PICOLYL)-AMIDE (MYDRIN M)].
PubMed:
[Phenylalanine as the precursor of tropic acid and benzoic acid. On the biosynthesis of tropane alkaloids. III].
PubMed:
[Determination of atropine, tropine and tropic acid in decomposed atropine solutions].
PubMed:
Tryptophan, precursor of tropic acid in Datura stramonium.
PubMed:
[Pharmacodynamic aspects of the use of a new tropic acid derivative in radio-diagnosis of the digestive tract].
PubMed:
[Chemically incompatible drug mixtures; inactivation of tropic acid ester & related compounds by means of basic solvents].
PubMed:
The metabolism of C14-labeled atropine and tropic acid in mice.
PubMed:
[Data on tropic acid esters and related compounds. II..].
PubMed:
Separation of tropic and atropic acids by partition and chromatography.
PubMed:
A new synthesis of d1-tropic acid.