29584-22-3

Usage

Uses

Used in Pharmaceutical Industry:
9-CIS-RETINOL ACETATE is used as a therapeutic agent for the treatment of visual disorders. Its application is primarily due to its retinal and vitamin A derivative properties, which contribute to the maintenance of healthy vision and the amelioration of various visual impairments.
Used in Nutritional Supplements:
9-CIS-RETINOL ACETATE is also used as an additive in the formulation of nutritional supplements, particularly those aimed at promoting eye health. Its inclusion in these products is justified by its vitamin A derivative nature, which is essential for proper vision and overall ocular health.
Used in Cosmetic Industry:
In the cosmetic industry, 9-CIS-RETINOL ACETATE is utilized as an ingredient in anti-aging and skin care products. Its application is based on its retinal derivative properties, which are known to promote skin cell regeneration and improve the overall appearance of the skin, reducing signs of aging and promoting a more youthful complexion.

Upstream product

• 108-24-7 acetic anhydride 
• 103905-09-5 1-acetoxy-6-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene 
• 127-47-9 Retinol acetate 
• 26586-02-7 (E)-4-acetoxy-2-methylcrotonaldehyde 
• 100183-86-6 [(2E,4Z)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; chloride 
• 414871-77-5 C₃₆H₄₈O₆S₂ 
• 56691-74-8 {[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene 
• 105096-76-2 1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene 
• 53282-28-3 [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride 
• 103905-01-7 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene 
• 103905-08-4 1-acetoxy-6-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene 
• 100183-85-5 [(E)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-en-4-ynyl]-triphenyl-phosphonium; chloride 
• 137047-33-7 1-[(E)-5-(1-Methoxy-1-methyl-ethoxy)-3-methyl-pent-3-en-1-ynyl]-2,2,6-trimethyl-cyclohexanol 
• 80713-62-8 5-(1-methoxy-1-methylethoxy)-3-methyl-3E-penten-1-yne 

Downstream Products

• 137121-53-0 Hexadecanoic acid (2E,4E,6E,8Z)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester 
• 137121-54-1 Hexadecanoic acid (2E,4Z,6E,8Z)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester 
• 137121-51-8 Acetic acid (2E,4Z,6E,8Z)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester 
• 137121-50-7 7-cis-retinyl acetate 
• 137121-52-9 (7Z,11Z)-Vitamin A 
• 6018-74-2 (7Z)-Vitamin A 
• 127-47-9 Retinol acetate 

Relevant academic research and scientific papers

Z -isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis

Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to correlate the experimentally observed Z-isomer distribution of retinoids with the energies of chemically important intermediates, which include ground- and excited-state potential energy surfaces. We also demonstrate the application of the current method by synthesizing gram-scale quantities of 9-cis-retinyl acetate 9Z-a. Operational simplicity and gram-scale ability make this chemistry a very practical solution to the problem of Z-isomer retinoid synthesis.

Catalytic synthesis of 9-cis-retinoids: Mechanistic insights

The regioselective Z-isomerization of thermodynamically stable all-trans retinoids remains challenging, and ultimately limits the availability of much needed therapeutics for the treatment of human diseases. We present here a novel, straightforward approach for the catalytic Z-isomerization of retinoids using conventional heat treatment or microwave irradiation. A screen of 20 transition metal-based catalysts identified an optimal approach for the regioselective production of Z-retinoids. The most effective catalytic system was comprised of a palladium complex with labile ligands. Several mechanistic studies, including isotopic H/D exchange and state-of-the-art quantum chemical calculations using coupled cluster methods indicate that the isomerization is initiated by catalyst dimerization followed by the formation of a cyclic, six-membered chloropalladate catalyst-substrate adduct, which eventually opens to produce the desired Z-isomer. The synthetic development described here, combined with thorough mechanistic analysis of the underlying chemistry, highlights the use of readily available transition metal-based catalysts in straightforward formats for gram-scale drug synthesis.

Process for preparation of allyl sulfone derivatives and intermediates for the preparation

The present invention relates to a process for producing an allyl sulfone derivative represented by the formula (3): wherein Ar is an optionally substituted aryl group, and the corrugated line means either one of E/Z geometrical isomers, or a mixture thereof, which is an intermediate for producing vitamin A, which process is characterized by reacting an aryl sulfinic acid or a salt thereof represented by the formula (2): ArSO2M (2) wherein Ar is as defined above, and M is hydrogen atom, sodium atom or potassium atom, with an allyl halide derivative represented by the formula (1): wherein X is a halogen atom, and Ar and the corrugated line are as defined above.

Process for producing retinol and intermediate compounds for producing the same

There are disclosed a disulfone compound of formula (1): wherein Ar denotes an aryl group that may have a substituent, R1 denotes a hydrogen atom or a protective group of a hydroxyl group and the wavy ine means that the disulfone compound is an E or Z geometrical isomer or i mixture thereof,a method for producing the same,intermediate compounds therefore anda process for producing retinol through the disulfone compound.

Preparation of (7Z) - and (7Z,11Z) - Vitamin A

An efficient access to (7Z)- and (7Z,11Z)-vitamin A is described. Following the addition of a C6-acetylenic building block to 2,6,6-trimethylcyclohexanone (2), dehydration of the tert. alcohol 3 and formation of the C15-Wittig salt, the (7Z)-geometry was introduced by partial hydrogenation of the triple bond over Raney-nickel. Following Wittig reaction with (E)-2-methyl-4-acetoxy-2-butenal gave a mixture of the title compounds 8 and 9 which could easily be separated.

REGIOSELECTIVE PHOTOISOMERISATION OF RETINOLACETATE

Regioselective photoisomerisation of retinolacetate undergoing at tri-substituted double bonds upon singlet and triplet excitation and its ionic photodissociation process originating from singlet excited state is reported.

Electro-organic Reactions. Part 20. Electrogenerated Bases, Ylide Formation, and Wittig Alkene Synthesis

Dicyano(fluoren-9-ylidene)methane (1a), dicyano(2,7-dibromofluoren-9-ylidene)methane (1b), and ethyl 2-cyano-2-fluoren-9-ylideneacetate (1c) may be cathodically reduced in N,N-dimethylforamide to give dianions which efficiently convert phosphonium salts into ylides.The potentials required are sufficiently modest to allow the electrogeneration of the bases in the presence of several phosphonium salts and of several aldehydes to give a convenient method of carrying out the Wittig alkene synthesis.This method has been explored for the synthesis of stilbene, 1,4-diphenylbutadiene, and vitamin A acetate.The basicity of the dianions varies according to the choice of electrolyte cation (Bu4N+ or Li+).The cations also have a marked effect on the stereochemical course of the reaction and, in particular, mixtures of alkenes are obtained in which the cis-isomer predominates in the presence of lithium ion; in the vitamin A acetate synthesis, the 11-cis-isomer constitutes 76percent of the product.The results are consistent with recent hypotheses concerning the mecahnism of the Wittig reaction.

Transient Phenomena in the Pulse Radiolysis of Retinyl Polyenes. 1. Radical Anions

The spectra and kinetics of formation and decay of radical anions of a number of retinyl polyenes have been studied in methanol and 2-propanol at room temperature, using pulse radiolysis and kinetic spectrophotometry.The bimolecular rate constants for the attachment of solvated electrons, e-MeOH, to the retinyl polyenes are in the diffusion-controlled limit (8.6 x 109-1.6 x 1010 M-1 s-1).The radical anions of retinol and retinol acetate have their spectral maxima at 370-390 nm, and undergo decay very slowly with second-order kinetics.On the other hand, the radical anions of retinal, retinal n-butylamine Schiff base, and retinoic acid/ester have spectral maxima at 430-510 nm, and decay by first-order kinetics in methanol with rate constants in the range 1 x 104-1 x 106 s-1.The decay rates of radical anions of retinal and retinoic acid/ester become considerably longer on going from methanol to less acidic alcohol, 2-propanol, suggesting that protonation by solvent is the major mode of their decay in protic media.In the case of retinal Schiff base, an additional slow process with bimolecular rate constant 9.0 x 107 M-1 s-1 im methanol is observed for the formation of radical anion and is ascribed to the electron-transfer reaction from the methanol radical, .CH2OH.