2432-99-7 Usage
Description
11-Aminoundecanoic acid, also known as Aminoundecanoic acid, is an organic compound characterized by an alkane chain with terminal carboxlic acid and amine groups. It is a white crystalline powder and is classified as a solid. 11-Aminoundecanoic acid is notable for its reactivity, as the amino group (NH2) can interact with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde), and other similar groups. The terminal carboxylic acid can also react with primary amine groups of activated NHS ester to form a stable amide bond. Furthermore, 11-Aminoundecanoic acid can be utilized as a PROTAC linker in the synthesis of protein degradation therapies, making it a valuable component in the development of novel pharmaceuticals.
Uses
Used in Pharmaceutical Applications:
11-Aminoundecanoic acid is used as a building block for the preparation of thapsigargin analogues, which are designed to target apoptosis in prostatic cancer cells. This application takes advantage of the compound's ability to form stable bonds and its reactivity with various chemical groups, making it a crucial component in the development of anticancer therapies.
Additionally, 11-Aminoundecanoic acid is used as a component in the synthesis of N-carboxyalkylpeptides containing extended alkyl residues. These peptides serve as matrix metalloproteinase inhibitors, which are essential in the treatment of various diseases, including cancer, by inhibiting the enzymes responsible for the breakdown of extracellular matrix proteins.
Preparation
ω-Aminoundecanoic acid is normally prepared from castor oil (glycerol
triricinoleate). Firstly the castor oil is subjected to methanolysis to yield the
methyl ester of ricinoleic acid and then the following route is used:
In the first step, the pyrolysis of methyl ricinoleate is carried out at about
500°C; the principal products are n-heptaldehyde and methyl undecylenate.
The latter is hydrolysed to give undecylenic acid which is treated with
hydrogen bromide in a non-polar solvent in the presence of a peroxide.
Under these conditions, reverse Markownikoff addition occurs and the main
product is ω-bromoundecanoic acid. This product is then treated with
ammonia to give ω-aminoundecanoic acid, which is a crystalline solid, m.p.
189°C.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
11-Aminoundecanoic acid is incompatible with strong oxidizing agents, strong acids and strong bases.
Fire Hazard
Flash point data for 11-Aminoundecanoic acid are not available; however, 11-Aminoundecanoic acid is probably combustible.
Flammability and Explosibility
Nonflammable
Safety Profile
Poison by ingestion. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.
Check Digit Verification of cas no
The CAS Registry Mumber 2432-99-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,3 and 2 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2432-99:
(6*2)+(5*4)+(4*3)+(3*2)+(2*9)+(1*9)=77
77 % 10 = 7
So 2432-99-7 is a valid CAS Registry Number.
InChI:InChI=1/C11H23NO2/c1-2-3-4-5-6-7-8-9-10(12)11(13)14/h10H,2-9,12H2,1H3,(H,13,14)
2432-99-7Relevant articles and documents
Syntheses of 12-aminododecanoic and 11-aminoundecanoic acids from vernolic acid
Ayorinde, Folahan O.,Nana, Erick Y.,Nicely, Pete D.,Woods, Anthony S.,Price, Elvis O.,Nwaonicha, Chukwuma P.
, p. 531 - 538 (1997)
12-Aminododecanoic acid and 11-aminoundecanoic acid, monomer precursors for nylon-12 and nylon-11, respectively, have been synthesized from vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid via a reaction sequence that includes the formation of 12-oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low-temperature recrystallization at -20°C, gave 51% vernolic acid (97% purity, m.p. 23-25°C). Hydrogenation afforded cis-12,13-epoxystearic acid (m.p. 52-54°C, lit. m.p. 52-54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12-oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12-oxododecanoic acid oxime, which was catalytically reduced to give 12-aminododecanoic acid with a yield greater than 85% and a melting point of 184-186°C (lit. m.p. 185-187C). 11-Aminoundecanoic acid was prepared from the 12-oxododecanoic acid oxime via a three-step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid (48% yield, m.p. 129-131°C, lit. m.p. 129-130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70-80°C to give 11-(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84-86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11-aminoundecanoic acid at 34% yield (m.p. 189-192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11-(methoxycarbonylamino)undecanoic acid is provided.
Method of Preparing Aminoundecane Acid and 11-Aminoundecanoic Acid or Structural Isomer Thereof by Hydroformylation Reaction
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Paragraph 0112-0116; 0119-0136, (2020/11/03)
The present invention relates to a method for preparing 11-aminoundecanoic acid or structural isomers thereof using a hydroformylation reaction. More particularly, the present invention is an eco-friendly method capable of preparing aminoundecanoic acid used as a monomer of polyamide and structural isomers thereof from an olefinic acid ester obtained through a metathesis reaction of oleic acid by means of hydroformylation, reductive amination reaction, and hydrolysis reaction, and capable of producing various polyamides having different physical properties according to a ratio of each isomer since the ratio of structural isomers can be adjusted according to a ligand.COPYRIGHT KIPO 2021
CONJUGATED CHEMICAL INDUCERS OF DEGRADATION AND METHODS OF USE
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Page/Page column 438, (2020/05/28)
The subject matter described herein is directed to antibody-CIDE conjugates (Ab-CIDEs), to pharmaceutical compositions containing them, and to their use in treating diseases and conditions where targeted protein degradation is beneficial.
Xn:Harmful;
