4627-61-6

Basic information

• Product Name: N-[(9Z)-octadec-9-enoyl]glutamic acid
• CAS NO: 4627-61-6
• Molecular Formula: C₂₃H₄₁NO₅
• Molecular Weight: 411.5753
• Mol File: 4627-61-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 611.4°C at 760 mmHg
• Flash Point: 323.6°C
• Density: 1.035g/cm³
• Vapor Pressure: 1.6E-16mmHg at 25°C
• Refractive Index: 1.492
• CAS DataBase Reference: N-[(9Z)-octadec-9-enoyl]glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(9Z)-octadec-9-enoyl]glutamic acid(4627-61-6)
• EPA Substance Registry System: N-[(9Z)-octadec-9-enoyl]glutamic acid(4627-61-6)

Safety Data

• Hazardous Substances Data: 4627-61-6(Hazardous Substances Data)

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 23150-65-4 L-glutamic dimethyl ester hydrochloride 
• 1413643-60-3 dimethyl (2S)-2-[[(Z)-octadec-9-enoyl]amino]pentanedioate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 112-80-1 cis-Octadecenoic acid 
• 56-86-0 L-glutamic acid 

Relevant articles and documents

CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF

Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).

Organic compounds

A flavour composition comprising a compound according to the formula (I) or edible salts thereof, wherein R1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, in which R3 is H or together with R2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration

N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.