Retinyl propionate
[CAS# 7069-42-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Retinyl propionate
• Synonyms: [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] propanoate
• Molecular Formula: C₂₃H₃₄O₂
• Molecular Weight: 342.51
• CAS Registry Number: 7069-42-3
• EC Number: 230-363-2
• SMILES: CCC(=O)OC/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(CCCC1(C)C)C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 453.7±14.0 ºC 760 mmHg (Calc.)^*
• Flash point: 122.7±18.5 ºC (Calc.)^*
• Index of refraction: 1.529 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Danger
• Hazard Statements: H360-H372-H413
• Precautionary Statements: P203-P260-P264-P270-P273-P280-P318-P319-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	1A	H360
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Retinyl propionate is a derivative of vitamin A, belonging to the family of retinoids that are widely studied and used for their biological and therapeutic properties. Chemically, it is the ester formed between retinol, the alcohol form of vitamin A, and propionic acid. This esterification stabilizes retinol and enhances its usability in practical applications, since free retinol is relatively unstable and easily degraded by light, heat, and oxygen. The development of retinyl esters such as retinyl propionate represented a significant advancement in making vitamin A derivatives more suitable for commercial and clinical use.

The discovery of retinyl propionate is tied to ongoing research into vitamin A metabolism and the search for stable and effective derivatives that could deliver the beneficial effects of retinoids while minimizing instability and irritation. Vitamin A was first isolated in the early 20th century and soon recognized for its essential role in vision, growth, and epithelial health. However, when applied directly in topical formulations, retinol was difficult to stabilize and often caused irritation. Researchers addressed these challenges by synthesizing esters of retinol, such as retinyl acetate, retinyl palmitate, and retinyl propionate. These esters were designed to act as storage forms of retinol that could be hydrolyzed enzymatically in the skin to release active retinol gradually.

The primary application of retinyl propionate is in dermatology and cosmetic science, particularly in anti-aging and skin-repair products. It is valued for its ability to improve skin texture, reduce the appearance of fine lines and wrinkles, and promote even skin tone. Once applied topically, retinyl propionate undergoes enzymatic hydrolysis to retinol, which can then be further oxidized to retinaldehyde and ultimately to retinoic acid, the biologically active form of vitamin A that binds to nuclear retinoic acid receptors. This stepwise activation allows for a milder and more gradual delivery of active retinoid effects compared to direct application of retinoic acid, which is potent but often irritating to the skin.

In addition to its role in reducing visible signs of aging, retinyl propionate is used to enhance epidermal turnover, promote collagen synthesis, and regulate keratinocyte differentiation. These effects contribute to smoother skin and reduced hyperpigmentation. Its relatively low irritation potential compared to other retinoids makes it a suitable choice for individuals with sensitive skin, and it is commonly included in creams, serums, and lotions formulated for long-term use.

Beyond cosmetic uses, retinyl propionate has been studied for its role in maintaining epithelial health and providing antioxidant protection. Retinoids, including retinyl esters, contribute to the protection of skin against oxidative stress induced by environmental factors such as ultraviolet radiation and pollution. The ester form enhances the stability of the compound during storage and formulation, ensuring that its beneficial effects are preserved until applied.

The introduction of retinyl propionate into dermatological practice illustrates the evolution of vitamin A chemistry from nutritional studies to therapeutic and cosmetic applications. By addressing the instability and irritation associated with retinol and retinoic acid, ester derivatives like retinyl propionate expanded the accessibility of retinoid benefits to a broader population. Its combination of stability, efficacy, and tolerability ensures its continued importance in modern skincare science and product development.

References

2023. The synergistic effect of retinyl propionate and hydroxypinacolone retinoate on skin aging. Journal of Cosmetic Dermatology, 22(8).
DOI: 10.1111/jocd.15662

2020. Enhanced retinoid response by a combination of the vitamin A ester retinyl propionate with niacinamide and a flavonoid containing Ceratoniasiliqua extract in retinoid responsive invitro models. International Journal of Cosmetic Science, 42(6).
DOI: 10.1111/ics.12669

1998. A clinicopathological study of the effects of topical retinyl propionate cream in skin photoageing. Clinical and Experimental Dermatology, 23(4).
DOI: 10.1046/j.1365-2230.1998.00331.x