2432-99-7

Basic information

• Product Name: 11-Aminoundecanoic acid
• Synonyms: NH2-(CH2)10-COOH;OMEGA-AMINOUNDECANOIC ACID;OMEGA-AMINOUNDECYLIC ACID;11-AMINOUNDECANOIC ACID;11-AMINOUNDECYLIC ACID;11-amino-undecanoicaci;11-aminoundecanoicacid(11-aa);aminoundecanoicacid
• CAS NO: 2432-99-7
• Molecular Formula: C₁₁H₂₃NO₂
• Molecular Weight: 201.31
• EINECS: 219-417-6
• Product Categories: Linear Core Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 2432-99-7.mol

Chemical Properties

• Melting Point: 188-191 °C(lit.)
• Boiling Point: 339.24°C (rough estimate)
• Flash Point: 156.324 °C
• Appearance: White/Crystalline Powder
• Density: 0.9896 (rough estimate)
• Vapor Pressure: 8.39E-05mmHg at 25°C
• Refractive Index: 1.4420 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: 2g/l
• PKA: 4.78±0.10(Predicted)
• Water Solubility: 2 g/L (20 ºC)
• BRN: 1767291
• CAS DataBase Reference: 11-Aminoundecanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 11-Aminoundecanoic acid(2432-99-7)
• EPA Substance Registry System: 11-Aminoundecanoic acid(2432-99-7)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: 52
• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: YQ2293000
• Hazardous Substances Data: 2432-99-7(Hazardous Substances Data)

Usage

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,.

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)

Upstream product

• 2834-05-1 11-bromoundecanoic acid 
• 100400-58-6 10-cyanodecanoic acid 
• 71-36-3 butan-1-ol 
• 17966-13-1 (+/-)-cis-12,13-epoxy-9(Z)-octadecenoic acid 
• 25601-41-6 methyl 9-decenoate 
• 201230-82-2 carbon monoxide 
• 10436-25-6 11-(tert-butoxycarbonylamino)undecanoic acid 
• 2380-27-0 methyl 12-oxooctadecanoate 
• 3669-80-5 11-hydroxyundecanoic acid 
• 144191-92-4 (11-hydroxyundecyl)carbamic acid tert-butyl ester 
• 27780-89-8 11-aminoundecan-1-ol 
• 1226980-96-6 methyl 10-cyano-2-decenoate 
• 854401-56-2 10-cyano-9-decenoate 
• 28691-27-2 methyl 11-aminoundecanoate 

Downstream Products

• 4403-42-3 11-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-undecanoic acid 
• 3422-91-1 11-<(Benzyloxycarbonyl)amino>undecansaeure 
• 10436-25-6 11-(tert-butoxycarbonylamino)undecanoic acid 
• 88574-07-6 11-(9-fluorenylmethyloxycarbonylamino)undecanoic acid 
• 7766-59-8 11-anilino-undecanoic acid 
• 918132-40-8 11-(3-benzoyl-benzoylamino)undecanoic acid 
• 16423-52-2 N-decyl-N-ethylpropanamide 
• 135672-69-4 N-(trifluoroacetyl) doxorubicin 14-O-<11'-(N-(p-anisyldiphenylmethyl) amino)> undecanoate 
• 1228927-28-3 (19S,23S)-tetra-tert-butyl-2-((1-(2-tertbutoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)-13,21-dioxo-2,14,20,22-tetraazapentacosane-1,19,23,25-tetracarboxylate 

Relevant articles and documents

Syntheses of 12-aminododecanoic and 11-aminoundecanoic acids from vernolic acid

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.

TARGET PROTEIN EED DEGRADATION-INDUCING DEGRADUCER, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DISEASES RELATED TO EED, EZH2, OR PRC2, COMPRISING SAME AS ACTIVE INGREDIENT

The present invention relates to a target protein degradation-inducing Degraducer, a preparation method thereof, and a pharmaceutical composition for preventing or treating diseases related to EED, EZH2, or PRC2 comprising same as an active ingredient. A novel compound represented by formula 1, according to the present invention is a Degraducer compound that induces degradation of a target protein, i.e., embryonic ectoderm development (EED) or polycomb repressive complex 2 (PRC2), utilizing cereblon E3 ubiquitin ligase, von Hippel-Lindau tumor suppressor (VHL) E3 ubiquitin ligase, mouse double minute 2 homolog (MDM2) E3 ubiquitin ligase, and cellular inhibitor of apoptosis protein 1 (cIAP) E3 ubiquitin ligase, wherein the compound has an aspect of remarkably achieving target protein degradation-inducing activity through a ubiquitin proteasome system (UPS), and therefore there is a useful effect in that it is possible to provide a pharmaceutical composition for preventing or treating diseases or conditions related to a target protein, and a functional health food composition for preventing or improving same, comprising said compound as an active ingredient.

Self-Adjuvanting Cancer Vaccines from Conjugation-Ready Lipid A Analogues and Synthetic Long Peptides

Self-adjuvanting vaccines, wherein an antigenic peptide is covalently bound to an immunostimulating agent, have been shown to be promising tools for immunotherapy. Synthetic Toll-like receptor (TLR) ligands are ideal adjuvants for covalent linking to peptides or proteins. We here introduce a conjugation-ready TLR4 ligand, CRX-527, a potent powerful lipid A analogue, in the generation of novel conjugate-vaccine modalities. Effective chemistry has been developed for the synthesis of the conjugation-ready ligand as well as the connection of it to the peptide antigen. Different linker systems and connection modes to a model peptide were explored, and in vitro evaluation of the conjugates showed them to be powerful immune-activating agents, significantly more effective than the separate components. Mounting the CRX-527 ligand at the N-terminus of the model peptide antigen delivered a vaccine modality that proved to be potent in activation of dendritic cells, in facilitating antigen presentation, and in initiating specific CD8+ T-cell-mediated killing of antigen-loaded target cells in vivo. Synthetic TLR4 ligands thus show great promise in potentiating the conjugate vaccine platform for application in cancer vaccination.

Method of Preparing Aminoundecane Acid and 11-Aminoundecanoic Acid or Structural Isomer Thereof by Hydroformylation Reaction

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

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.

Preparation method of 11-aminoundecanoic acid

The invention provides a preparation method of 11-aminoundecanoic acid. The method comprises the following steps: 1) dissolving 9-hydroxyl pelargonic acid or 9-hydroxyl pelargonate in a solvent and carrying out selective oxidization in the presence of an oxidant to prepare 9-oxo pelargonic acid or 9-oxo pelargonate; 2) dissolving 9-oxo pelargonic acid or 9-oxo pelargonate and cyanoacetate in a solvent for knoevenagel condensation reaction to obtain a compound as shown in a formula III; 3) continuously carrying out a hydrolysis reaction on the product obtained in the step 2) and carrying out acidification to obtain 2-cyano cyanohendecene-2-diacid; 4) carrying out a selective decarboxylic reaction on the product obtained in the step 3) to obtain a compound as shown in a formula V: 10-cyno-10-ene capric acid; and 5) adding a catalyst into the 10-cyno-10-ene capric acid obtained in the step 4), replacing the mixture with nitrogen and hydrogen successively for a hydrogenation reduction reaction, and refining a coarse product to obtain the 11-aminoundecanoic acid.

PROCESS FOR THE CO-PRODUCTION OF LONG CHAIN AMINO ACIDS AND DIBASIC ACIDS

There is disclosed a process for the co-production of long chain ω-amino acid and long chain dibasic acid, comprising: (1) reacting long chain ketoacid derivative with hydroxylamine or subjecting ketoacid derivative to an ammoximation to yield oxime derivative; (2) subjecting oxime derivative to Beckmann rearrangement to yield a mixture of mixed amide derivatives; (3) hydrolyzing the mixed amide derivatives to produce long chain ω-amino acid and long chain dibasic acid.

Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines

Running two two-step cascades in parallel anti-sense to transform an alcohol to an amine allowed the conversion of ω-hydroxy fatty acids (ω-HFAs) and α,ω-diols to the corresponding ω-amino fatty acids (ω-AmFAs) and α,ω-diamines, respectively. The network required only two enzymes namely an aldehyde reductase (AHR) and a transaminase (TA). Benzylamine served on the one hand as amine donor and on the other hand after deamination to benzaldehyde also as oxidant. All ω-HFAs tested were efficiently transformed to their corresponding ω-AmFAs using purified enzymes as well as a whole-cell system, separately expressing both the enzymes, with conversions ranging from 80-95%. Additionally, a single-cell co-expressing all enzymes successfully produced the ω-AmFAs as well as the α,ω-diamines with >90% yield. This system was extended by employing a lactonase, enabling the transformation of ?-caprolactone to its corresponding ω-AmFA with >80% conversion.

Process for producing long chain amino acids and dibasic acids

There is disclosed a process for the production of long chain amino acid and long chain dibasic acid, comprising: (1) reacting long chain keto fatty acid with hydroxylamine or subjecting keto fatty acid to an ammoximation reaction to yield an oxime fatty acid; (2) subjecting the oxime fatty acid to the Beckmann rearrangement to yield a mixture of two amide fatty acids; (3) hydrolyzing the mixed amide fatty acids to produce long chain amino acid, long chain dibasic acid, short chain alkylamine, and alkanoic acid.

PREPARATION OF AMINO ACIDS AND AMINO ACID DERIVATIVES

The invention relates to a method for synthesizing amino acids or amino acid derivatives involving cross metathesis of functionalized olefins and a tandem amination-reduction process. Amino acids and amino acid derivatives present many interesting physical and chemical properties finding many uses in the automotive, fuel, electronic, and textile industries.