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T89206

Sigma-Aldrich

Tropic acid

98%

Synonym(s):

2-Phenylhydracrylic acid, 3-Hydroxy-2-phenylpropionic acid

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About This Item

Linear Formula:
C6H5CH(CH2OH)CO2H
CAS Number:
552-63-6
Molecular Weight:
166.17
Beilstein:
2209199
EC Number:
209-020-6
MDL number:
MFCD00004255
UNSPSC Code:
12352100
PubChem Substance ID:
24900574
NACRES:
NA.22

Assay

98%

mp

116-118 °C (lit.)

SMILES string

OCC(C(O)=O)c1ccccc1

InChI

1S/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)

InChI key

JACRWUWPXAESPB-UHFFFAOYSA-N

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Application

Tropic acid can be used as a substrate in:
  • Esterification of carboxylic acids and alcohols in the presence of dried Dowex H+/NaI catalyst system.
  • Multistep synthesis of cyclic pentadepsipeptides.
  • Synthesis of an isocoumarin derivative by reacting with tetracyanobenzene (TCNB) via multicomponent photo reaction.

Tropic acid is used in the synthesis of (−)-anisodine, atropine and hyoscyamine.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tropane alkaloids in pharmaceutical and phytochemical analysis.
Gadzikowska, MARIA and Grynkiewicz, GRZEGORZ
Acta Poloniae Pharmaceutica, 59(2), 149-160 (2002)
Photo-multicomponent reactions leading to the construction of isocoumarins and large ring lactone precursors
Lu Z, et al.
Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology, 8(2), 217-223 (2009)
Synthesis of conformationally restricted cyclic pentadepsipeptides via direct amide cyclization
Koch KN, et al.
Tetrahedron, 57(12), 2311-2326 (2001)
Green and Efficient Esterification Method Using Dried Dowex H+/NaI Approach
Turhanen PA, et al.
ACS Omega, 4(5), 8974-8984 (2019)
Junbiao Chang et al.
European journal of medicinal chemistry, 41(3), 397-400 (2006-01-18)
-Anisodine (l-6,7-epoxy-3-tropyl-alpha-hydroxytropate), which was isolated from the medicinal plant Scopolia tanguticus Maxim, was the first efficiently prepared using 6-beta-acetyltropine as the starting material via a key step of the Sharpless asymmetric dihydroxylation (AD). The intermediate compounds 10 and 11 showed
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