130443-70-8

Basic information

• Product Name: (S)-6-Amino-2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-hexanoic acid
• Synonyms: (S)-6-Amino-2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-hexanoic acid
• CAS NO: 130443-70-8
• Molecular Weight: 412.616
• Mol File: 130443-70-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-6-Amino-2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-hexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-6-Amino-2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-hexanoic acid(130443-70-8)
• EPA Substance Registry System: (S)-6-Amino-2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-hexanoic acid(130443-70-8)

Safety Data

• Hazardous Substances Data: 130443-70-8(Hazardous Substances Data)

Upstream product

• 56-87-1 L-lysine 
• 116-31-4 all-trans-Retinal 

Downstream Products

• 56-87-1 L-lysine 
• 116-31-4 all-trans-Retinal 

Relevant articles and documents

Synthesis and characterization of N-retinylidene derivatives of polar amino acids

Water-soluble N-retinylideneamino acids were synthesized and their physicochemical characteristics studied. The latter included the kinetics of hydrolysis in water, aqueous ethanol, physiological solution, and 0.1 M phosphate buffer, pH 7.0. The observed hydrolysis rate constants for N-retinylideneamino acids were shown to decrease in the order Ser > Asp > Taur > Met > Lys.

Retinylidene Schiff bases in surfactant-solubilized water pools in heptane

All-trans-retinal (1) was reacted with n-butylamine in sodium bis(2-ethylhexyl)sulfosuccinate (AOT) reverse micelles in heptane to form all-trans-N-retinylidene-n-butylamine Schiff bases (2).The extent of protonation of 2 by 3-chloropropionic acid (CPA) to give 3 in AOT reverse micelles in heptane was found to depend on the ratio of (CPA) to (2), as well as on / (i.e., on the ω value).At any given (2) and ω values, increasing amounts of CPA increased the protonation and at any given constant (2) and (CPA), increasing ω values also increased the protonation.Over a period of 24 hours, there was only 4percent decomposition of 2 in AOT reverse micelles in heptane at ω= 24.Conversely, in three hours, 23percent of 3 decomposed in the same system.The trans to cis photoisomerization of 2 in heptane occurred at a much faster rate in the presence of AOT reverse micelles than in their absence.The appearance of carboxylate peaks (FTIR, 1400-1500 cm-1) indicated that the larger the AOT solubilized water pools, the greater the CPA dissociation. 1 also reacted with the α-NH2 group of l-lysine (4) in AOT reverse micelles in heptane to give the corresponding Schiff base 6.Protonation of 6 occurred either intramolecularly or by reaction with unreacted 4.These results were discussed in terms of rhodopsin protonations.Key words: retinylidene Schiff bases, reverse micelles, protonation of Schiff bases, trans to cis photodimersization.