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11-Aminoundecanoic acid

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11-Aminoundecanoic acid Basic information

Product Name:
11-Aminoundecanoic acid
Synonyms:
  • 11-AMINOUNDECANOIC ACID
  • 11-AMINOUNDECYLIC ACID
  • 11-amino-undecanoicaci
  • 11-AMINOUNDECANOIC ACID FOR SYNTHESIS
  • 11-amino-n-undecanoic acid
  • 11-Amino-undecansaeure
  • 11-Aminoundecanoic acid≥ 99% (Titration)
  • NH2-(CH2)10-COOH
CAS:
2432-99-7
MF:
C11H23NO2
MW:
201.31
EINECS:
219-417-6
Product Categories:
  • Linear Core Amino Acids
  • Peptide Synthesis
  • Unnatural Amino Acid Derivatives
Mol File:
2432-99-7.mol
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11-Aminoundecanoic acid Chemical Properties

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
InChIKey
GUOSQNAUYHMCRU-UHFFFAOYSA-N
LogP
-0.16 at 20℃
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)
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Safety Information

Risk Statements 
52
Safety Statements 
24/25
WGK Germany 
1
RTECS 
YQ2293000
HS Code 
29224995
Hazardous Substances Data
2432-99-7(Hazardous Substances Data)
Toxicity
LDLo orl-rat: 14,700 mg/kg NTPTR* NTP-TR-216,82

MSDS

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11-Aminoundecanoic acid Usage And Synthesis

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.

Uses

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.

Definition

ChEBI: 11-Aminoundecanoic acid is a medium-chain fatty acid.

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.

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,.

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