ChemicalBook CAS DataBase List 79-81-2

79-81-2

Name	Retinol palmitate
CAS	79-81-2
EINECS(EC#)	201-228-5
Molecular Formula	C36H60O2
MDL Number	MFCD00019414
Molecular Weight	524.86
MOL File	79-81-2.mol

Synonyms

ALL TRANS-RETINOL PALMITATE AROVIT RETINOL PALMITATE RETINOL PALMITATE ALL TRANS RETINOL PALMITATE ALL TRANS ISOMER RETINOL PALMITATE TYPE IV: ALL TRANS RETINYL PALMITATE VITAMIN A PALMITATE VITAMINE A PALMITATE 3,7-Dimethyl-9-(2,6,6,-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol palmitate all-trans-retinopalmitate Ester found in fish liver oils Optovit-A Retinol, hexadecanoate Retinol,hexadecanate retinol,hexadecanoate retinol palmitate type iv sigma grade RETINOL PALMITATE, 100MG, NEAT RETINOL PALMITATE TYPE VI VITAMIN A PALMITATE 1.7 MILLION IU/G

Chemical Properties

Melting point	28-29℃
Boiling point	546.51°C (rough estimate)
density	0.9668 (rough estimate)
refractive index	1.5250 (estimate)
Fp	194℃
storage temp.	2-8°C
solubility	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
form	oil
pka	-7
color	Light Yellow to Yellow Low Melting
Specific Gravity	0.90～0.93 (20℃)
biological source	synthetic (organic)
Water Solubility	Soluble in chloroform, ether, and vegetable oils. Insoluble in water.
Merck	13,10073
BRN	1917366
Specific Activity	~1,800,000USP units/g
BCS Class	4
Stability:	Light Sensitive
Major Application	cleaning products cosmetics food and beverages personal care pharmaceutical (small molecule) vitamins, nutraceuticals, and natural products
Cosmetics Ingredients Functions	SKIN CONDITIONING - MISCELLANEOUS
InChIKey	VYGQUTWHTHXGQB-YFAKFODJSA-N
SMILES	O(C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(CCCC1(C)C)C)C(=O)CCCCCCCCCCCCCCC
LogP	15.51 at 25℃
Uses	retinyl palmitate(79-81-2) is a skin conditioner. This retinoid is considered a milder version of retinoic acid, given its conversion properties. once on the skin, it converts to retinol, which in turn converts to retinoic acid. Physiologically, it is credited with increasing R epidermal thickness, stimulating the production of more epidermal protein, and increasing skin elasticity. Cosmetically, retinyl palmitate is used to reduce the number and depth of fine lines and wrinkles, and prevent skin roughness resulting from uV exposure. Secondary reactions such as erythema, dryness, or irritation are not associated with retinyl palmitate. It is even more effective when used in combination with glycolic acid because it achieves greater penetration. In the united States, its maximum usage level in cosmetic formulations is 2 percent. Retinyl palmitate is the ester of retinol and palmitic acid. less more
CAS DataBase Reference	79-81-2(CAS DataBase Reference)
NIST Chemistry Reference	Vitamin a palmitate(79-81-2)
EPA Substance Registry System	79-81-2(EPA Substance)

Safety Data

Symbol(GHS)	GHS08
Signal word	Danger
Hazard statements	H360D-H412
Precautionary statements	P202-P273-P280-P308+P313-P405-P501
Hazard Codes	T,Xn
Risk Statements	R63:Possible risk of harm to the unborn child. less more
Safety Statements	S53:Avoid exposure-obtain special instruction before use . S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S36/37:Wear suitable protective clothing and gloves . less more
RIDADR	UN1170 - class 3 - PG 2 - Ethanol, solution
WGK Germany	3
RTECS	VH6860000
F	8-10-23
TSCA	Yes
REACH Registrations	Active
HS Code	29362100
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Aquatic Chronic 3 Repr. 1B
Safety Profile	Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. less more
Toxicity	LD50 (10 day) in mice, rats (mg/kg): 6060, 7910 orally (Kamm) less more

Hazard Information

Chemical Properties

95.0-100.5% Absorbance @325 nm ≥0.85%

Definition

ChEBI:All-trans-retinyl palmitate is an all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis. It has a role as an Escherichia coli metabolite, a human xenobiotic metabolite and an antioxidant. It is a retinyl palmitate and an all-trans-retinyl ester. It is functionally related to an all-trans-retinol.

General Description

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards.
Retinyl palmitate belongs to a category of compounds called retinoids, which are chemically similar to vitamin A. It exhibits a beneficial effect on vision, skin and immune function, inhibits cell proliferation and prevents cancer. It is an important dietary as well as a therapeutic compound.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Review: Vitamin A metabolism.

Side effects

Vitamin A palmitate(79-81-2) is fat-soluble and is stored in the body's fatty tissue. Therefore, excessive levels of vitamin A palmitate can lead to toxicity and liver disease. This is more likely to occur when taking supplements than when consuming them from food. People with liver disease should not take vitamin A palmitate supplements. Excessive doses of vitamin A supplements have been linked to birth defects, including malformations of the eyes, lungs, skull and heart. They are not recommended for pregnant women. Regular high doses of vitamin A letter source can lead to depression, dry skin, and muscle and joint pain.

Synthesis

112-39-0

127-47-9

79-81-2

Synthesis of (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate from methyl palmitate and (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6, 8-tetraen-1-yl palmitate in the following general procedure: 3000 kg of vitamin A acetate (compound of formula Ia) in crystalline form and 2750 kg of methyl palmitate (compound of formula Ia) were added to the reactor. Subsequently, 10 kg of sodium hydroxide was dissolved in about 60 liters of methanol and this solution was added to the above mixture. The reaction mixture was heated to 55°C and the system pressure was reduced to 1500-2200 Pascal. The reaction lasted for about 3 hours, during which time the main by-product, methyl acetate, was continuously removed by distillation. Reaction termination was achieved by addition of water and carbon dioxide. Finally, the target product vitamin A palmitate (compound of formula IIIa) was isolated from the reaction solution by extraction in 96% yield.

storage

Store at -20°C

Purification Methods

The palmitate is separated from retinol by column chromatography on water-deactivated alumina with hexane containing a very small percentage of acetone. It is also chromatographed on TLC silica gel G, using pet ether/isopropyl ether/acetic acid/water (180:20:2:5) or pet ether/acetonitrile/acetic acid/water (190:10:1:15) to develop the chromatogram. It is then recrystallised from propylene at low temperature (below -47o). [Beilstein 6 IV 4135.]

References

[1] Patent: WO2014/23772, 2014, A1. Location in patent: Page/Page column 9

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