87-29-6 Usage
Description
Anthranilic Acid Cinnamyl Ester is a chemical compound that is a brownish or reddish-yellow powder or light yellow solid with a fruity taste. It has a balsamic, fruity odor somewhat reminiscent of grape. It is water insoluble and soluble in ethanol, ethyl ether, and chloroform.
Uses
Used in Food Industry:
Anthranilic Acid Cinnamyl Ester is used as a flavoring agent in the food industry. It imparts a fruity and characteristically balsamic flavor to food products.
Used in Soap and Perfume Industry:
Anthranilic Acid Cinnamyl Ester is used as a fragrance in soaps and perfumes. Its balsamic, fruity odor adds a pleasant scent to these products.
Used in Chemical Synthesis:
Anthranilic Acid Cinnamyl Ester is obtained by chemical synthesis and can be used as a starting material for the synthesis of other chemical compounds.
Preparation
By esterification of anthranilic acid with cinnamyl alcohol.
Air & Water Reactions
ANTHRANILIC ACID CINNAMYL ESTER is sensitive to oxidation and hydrolysis. Insoluble in water.
Reactivity Profile
ANTHRANILIC ACID CINNAMYL ESTER is sensitive to oxidation and hydrolysis. ANTHRANILIC ACID CINNAMYL ESTER is subject to photooxidation. ANTHRANILIC ACID CINNAMYL ESTER reacts with various aldehydes, forming highly colored compounds.
Hazard
Questionable carcinogen.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition ANTHRANILIC ACID CINNAMYL ESTER emits toxic fumes of nitrogen oxides.
Fire Hazard
Flash point data for ANTHRANILIC ACID CINNAMYL ESTER are not available; however, ANTHRANILIC ACID CINNAMYL ESTER is probably combustible.
Safety Profile
Suspected carcinogen
with experimental carcinogenic and
neoplastigenic data. Mutation data reported.
See also ESTERS. Combustible liquid.
When heated to decomposition it emits
toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 87-29-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 87-29:
(4*8)+(3*7)+(2*2)+(1*9)=66
66 % 10 = 6
So 87-29-6 is a valid CAS Registry Number.
InChI:InChI=1/C16H15NO2/c17-15-11-5-4-10-14(15)16(18)19-12-6-9-13-7-2-1-3-8-13/h1-11H,12,17H2/b9-6+
87-29-6Relevant articles and documents
Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists
Roell, Daniela,R?sler, Thomas W.,Hessenkemper, Wiebke,Kraft, Florian,Hauschild, Monique,Bartsch, Sophie,Abraham, Tsion E.,Houtsmuller, Adriaan B.,Matusch, Rudolf,van Royen, Martin E.,Baniahmad, Aria
, p. 59 - 70 (2019/02/01)
Androgen receptor (AR) antagonists are used for hormone therapy of prostate cancer (PCa). However resistance to the treatment occurs eventually. One possible reason is the occurrence of AR mutations that prevent inhibition of AR-mediated transactivation by antagonists. To offer in future more options to inhibit AR signaling, novel chemical lead structures for new AR antagonists would be beneficial. Here we analyzed structure-activity relationships of a battery of 36 non-steroidal structural variants of methyl anthranilate including 23 synthesized compounds. We identified structural requirements that lead to more potent AR antagonists. Specific compounds inhibit the transactivation of wild-type AR as well as AR mutants that render treatment resistance to hydroxyflutamide, bicalutamide and the second-generation AR antagonist enzalutamide. This suggests a distinct mode of inhibiting the AR compared to the clinically used compounds. Competition assays suggest binding of these compounds to the AR ligand binding domain and inhibit PCa cell proliferation. Moreover, active compounds induce cellular senescence despite inhibition of AR-mediated transactivation indicating a transactivation-independent AR-pathway. In line with this, fluorescence resonance after photobleaching (FRAP) - assays reveal higher mobility of the AR in the cell nuclei. Mechanistically, fluorescence resonance energy transfer (FRET) - assays indicate that the amino-carboxy (N/C)-interaction of the AR is not affected, which is in contrast to known AR-antagonists. This suggests a mechanistically novel mode of AR-antagonism. Together, these findings indicate the identification of a novel chemical platform as a new lead structure that extends the diversity of known AR antagonists and possesses a distinct mode of antagonizing AR-function.
