Retiny acetate

Structural formula
General
Surname	Retiny acetate
other names	Retinol acetate; all- trans -retinylacetate; Vitamin A acetate; RETINYL ACETATE ( INCI ) ;
Molecular formula	C 22 H 32 O 2
Brief description	(dark) yellow crystalline form
External identifiers / databases
EC number	204-844-2
ECHA InfoCard	100.004.405
PubChem	638034
Wikidata	Q7316808
properties
Molar mass	328.50 g mol −1
Physical state	firmly
Melting point	57 to 58 ° C [( E , E , E , E ) isomer]
solubility	almost insoluble in water (0.01 mg · l –1 ); slightly soluble in chloroform , dichloromethane and ethyl acetate ;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 360-413
	P: 201-273-308 + 313
Toxicological data	2000 mg kg −1 ( LD 50 , rat , oral ) ; 1.37 mg l −1 ( LC 50 , rainbow trout , 96 h ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Retinylacetate is a chemical compound that is used in the cosmetics and pharmaceutical industries. It is the ester between acetic acid and retinol (vitamin A).

properties

Retinylacetate has a self-ignition temperature of 395 ° C.

use

Ingredients of cough drops

Retinylacetate is used in cosmetics in creams (for example: eye cream), body lotions and sunscreens. It is mainly added because the substance is said to have an anti-aging effect. In addition, it can be used for prophylaxis against marginal periodontitis. That is why it is sometimes found in toothpastes. Other products that contain it are, for example, cough drops (see picture: Ingredients of cough drops). Since the human body can convert retiny acetate into vitamin A and it is more heat and light resistant than vitamin A, it is often added as a vitamin A substitute.

Biological effect

In an experimental study, the absorption behavior of β- ¹⁴ C-carotene, ¹⁴ C-retinol and ³ H-retinylacetate was examined comparatively. The uptake of β-carotene was 6% to 20% and that of retinol and retinylacetate were 30% to 67%. In the body there are esterases in the intestines, liver and kidneys that are able to hydrolyze the retinylacetate to retinol.

The inhibitory properties of retinylacetate in NMU and DBMA breast-induced breast carcinogenesis have been shown in studies. The mechanism by which retinoids inhibit the carcinogen is not known. No toxic effects of retinylacetate were observed in a study published in the journal Nature . The effect is enhanced by 4-hydroxy (phenyl) retinamide (4-HPR). Results were obtained from 94% of the diseased rats in the placebo group and 15% in the treated group.

Individual evidence

↑ Entry on RETINYL ACETATE in the CosIng database of the EU Commission, accessed on December 29, 2019.
↑ ^a ^b ^c ^d ^e ^f ^g Data sheet retinylacetate from Sigma-Aldrich , accessed on December 29, 2019 ( PDF ).
^ RH Beutel, DF Hinkley, PI Pollak (Ed.): Conversion of vitamin A acetate to retrovitamin A acetate . Journal of American Chemical Society, 1955, Volume 77, pp. 5166-5167.
↑ TRC: 127-47-9 | Vitamin A Acetate | (all-E) -3,7-dimethyl-9- (2,6,6-trimethyl-1-cyclohexen-1-yl) -2-4,6,8-nonatetraen-1-ol acetate; Retinyl acetates; Vitamin A1 Acetate; all-trans-retinol acetates; | C₂₂H₃₂O₂ | TRC , accessed January 11, 2020
↑ Bund for Risk Assessment (Ed.): Vitamin A: Intake via cosmetic products should be limited , pp. 3–4, 2014, accessed on September 29, 2017.
↑ Patent US5885595 : Cosmetic composition with a retinol fatty acid ester. Published on March 23, 1999 , Inventors: Joseph Corey, Peter Ladislav Dorogi, Alan Joel Meyers, Anthony Vargas. ‌
↑ H. Heseker, A. Stahl (Ed.): Vitamin A: Physiology, functions, occurrence, reference values and supply in Germany . In: Ernahrung Umschau , Volume 9, 2010, p. 482.
↑ K. Lang (Ed.): Biochemistry of Nutrition . Springerverlag, Berlin, ed. 3, 1974, ISBN 978-3-662-41464-4 , e-book, p. 395.
^ RC Moon, CJ Grubbs, MB Sporn, d. G. Dawn (Ed.): Retinyl acetate inhibits mammary carcinogenesis induced by N-methyl-N-nitrosourea. In: Nature. Volume 267, No. 5612, pp. 620,621, 1977, doi : 10.1038 / 267620a0 .
↑ A. Lupulescu (Ed.): Hormones and Vitamins in Cancer Treatment . CRC Press, 1990, ISBN 0-8493-5973-2 , p. 247.

[CosIng-1] Entry on RETINYL ACETATE in the CosIng database of the EU Commission, accessed on December 29, 2019.

[SIGMA-2] ↑ ^a ^b ^c ^d ^e ^f ^g Data sheet retinylacetate from Sigma-Aldrich , accessed on December 29, 2019 ( PDF ).

[Beutel-3] RH Beutel, DF Hinkley, PI Pollak (Ed.): Conversion of vitamin A acetate to retrovitamin A acetate . Journal of American Chemical Society, 1955, Volume 77, pp. 5166-5167.

[trc-canada.com-4] TRC: 127-47-9 | Vitamin A Acetate | (all-E) -3,7-dimethyl-9- (2,6,6-trimethyl-1-cyclohexen-1-yl) -2-4,6,8-nonatetraen-1-ol acetate; Retinyl acetates; Vitamin A1 Acetate; all-trans-retinol acetates; | C₂₂H₃₂O₂ | TRC , accessed January 11, 2020

[BFR-5] Bund for Risk Assessment (Ed.): Vitamin A: Intake via cosmetic products should be limited , pp. 3–4, 2014, accessed on September 29, 2017.

[US_Patent-6] Patent US5885595 : Cosmetic composition with a retinol fatty acid ester. Published on March 23, 1999 , Inventors: Joseph Corey, Peter Ladislav Dorogi, Alan Joel Meyers, Anthony Vargas. ‌

[Heseker-7] H. Heseker, A. Stahl (Ed.): Vitamin A: Physiology, functions, occurrence, reference values and supply in Germany . In: Ernahrung Umschau , Volume 9, 2010, p. 482.

[Hosseini-Savari-8] K. Lang (Ed.): Biochemistry of Nutrition . Springerverlag, Berlin, ed. 3, 1974, ISBN 978-3-662-41464-4 , e-book, p. 395.

[9] RC Moon, CJ Grubbs, MB Sporn, d. G. Dawn (Ed.): Retinyl acetate inhibits mammary carcinogenesis induced by N-methyl-N-nitrosourea. In: Nature. Volume 267, No. 5612, pp. 620,621, 1977, doi : 10.1038 / 267620a0 .

[Lupulescu-10] A. Lupulescu (Ed.): Hormones and Vitamins in Cancer Treatment . CRC Press, 1990, ISBN 0-8493-5973-2 , p. 247.