11-Aminoundecanoic acid
Synonym(s):11-Aminoundecanoic acid
- CAS NO.:2432-99-7
- Empirical Formula: C11H23NO2
- Molecular Weight: 201.31
- MDL number: MFCD00008150
- EINECS: 219-417-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-12-18 14:08:52
What is 11-Aminoundecanoic acid?
Description
Aminoundecanoic acid can be used as a PROTAC linker in the synthesis of PROTACs. Aminoundecanoic acid is an alkane chain with terminal carboxlic acid and amine groups. The amino group (NH2) is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The terminal carboxylic acid can react with primary amine groups of activated NHS ester to form a stable amide bond.
Chemical properties
White crystalline powder
Chemical properties
11-Aminoundecanoic acid is a solid.
The Uses of 11-Aminoundecanoic acid
11-Aminoundecanoic Acid is used to prepare thapsigargin analogues targeting apoptosis to prostatic cancer cells. It is also used to synthesize N-carboxyalkylpeptides containing extended alkyl residues at P1''as matrix metalloproteinase inhibitors.
Preparation
|?-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 |?-bromoundecanoic acid. This product is then treated with ammonia to give |?-aminoundecanoic acid, which is a crystalline solid, m.p. 189??C.
Definition
ChEBI: 11-Aminoundecanoic acid is a medium-chain fatty acid.
General Description
White crystalline solid or powder.
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
Non flammable
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,.
Properties of 11-Aminoundecanoic acid
Melting point: | 188-191 °C (lit.) |
Boiling point: | 339.24°C (rough estimate) |
Density | 0.9896 (rough estimate) |
refractive index | 1.4420 (estimate) |
storage temp. | Store below +30°C. |
solubility | 2g/l |
form | Crystalline Powder |
pka | 4.78±0.10(Predicted) |
color | White |
Water Solubility | 2 g/L (20 ºC) |
BRN | 1767291 |
CAS DataBase Reference | 2432-99-7(CAS DataBase Reference) |
IARC | 3 (Vol. 39, Sup 7) 1987 |
EPA Substance Registry System | 11-Aminoundecanoic acid (2432-99-7) |
Safety information for 11-Aminoundecanoic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 11-Aminoundecanoic acid
InChIKey | GUOSQNAUYHMCRU-UHFFFAOYSA-N |
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