29584-22-3

Basic information

• Product Name: 9-CIS-RETINOL ACETATE
• Synonyms: 9-CIS-RETINOL ACETATE;9-cis-Retinyl acetate;9-cis-Vitamin A acetate;9-cis-Vitamin A1 acetate
• CAS NO: 29584-22-3
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.48828
• Product Categories: Retinoids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 29584-22-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 440.5±14.0 °C(Predicted)
• Appearance: /
• Density: 0.968±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate
• CAS DataBase Reference: 9-CIS-RETINOL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-CIS-RETINOL ACETATE(29584-22-3)
• EPA Substance Registry System: 9-CIS-RETINOL ACETATE(29584-22-3)

Safety Data

• Hazardous Substances Data: 29584-22-3(Hazardous Substances Data)

Usage

Description

9-CIS-RETINOL ACETATE, a retinal derivative and a vitamin A derivative, is a light syrup with significant applications in the treatment of visual disorders. It plays a crucial role in maintaining healthy vision and has been found effective in addressing various visual impairments.

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

• 414871-77-5 C₃₆H₄₈O₆S₂ 
• 26586-02-7 (E)-4-acetoxy-2-methylcrotonaldehyde 
• 53282-28-3 [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride 
• 127-47-9 Retinol acetate 
• 108-24-7 acetic anhydride 
• 105096-76-2 1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene 
• 103905-09-5 1-acetoxy-6-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 37905-03-6 8-hydroxygeranyl acetate 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 56691-74-8 {[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene 
• 103905-08-4 1-acetoxy-6-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene 
• 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 
• 100183-86-6 [(2E,4Z)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; chloride 

Downstream Products

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

Relevant articles and documents

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.

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.

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.