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Vitamin A palmitate structure
Vitamin A palmitate structure

Vitamin A palmitate

Iupac Name:[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
CAS No.: 79-81-2
Molecular Weight:524.8604
Modify Date.: 2022-11-29 03:05

Retinyl palmitate is an ester of Retinol and is the major form of vitamin A found in the epidermis. Retinyl palmitate has been widely used in pharmaceutical and cosmetic formulations.


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 derives from an all-trans-retinol.|Retinyl Palmitate is a naturally-occurring phenyl analogue of retinol (vitamin A) with potential antineoplastic and chemopreventive activities. As the most common form of vitamin A taken for dietary supplementation, retinyl palmitate binds to and activates retinoid receptors, thereby inducing cell differentiation and decreasing cell proliferation. This agent also inhibits carcinogen-induced neoplastic transformation, induces apoptosis in some cancer cell types, and exhibits immunomodulatory properties. (NCI04)

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1. Names and Identifiers
1.1 Name
Vitamin A palmitate
1.2 Synonyms

[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] hexadecanoate [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate all-trans-retinyl palmitate ALL-TRANS-RETINYLPALMITATE EINECS 201-228-5 MFCD00019414 O-hexadecanoylretinol O-Palmitoylretinol Retinol hexadecanoate Retinol, O-(1-oxohexadecyl)- Retinyl palmitate Retinylpalmitat VITAMIN A PALMITATE(RETINYL PALMITATE)(P) VITAMIN A PALMITATE(RETINYL PALMITATE)(RG) VITAMINAPALMITATE,LIQUIDINOIL,1MILLIONIU/G VITAMINAPALMITATE,USP VitaminAPalmitateinOil

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C36H60O2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
607.5 °C at 760 mmHg
2.1 Refractive index
2.1 Flash Point
79.7 °C
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Appearance
2.2 Storage
Keep Cold.
2.3 Water Solubility
Soluble in chloroform, ether, and vegetable oils. Insoluble in water.
2.4 StorageTemp
3. Use and Manufacturing
3.1 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.] Vitamin A palmitateSupplier
3.2 Usage
4. Safety and Handling
4.1 Symbol
GHS02, GHS07
4.1 Hazard Codes
4.1 Signal Word
4.1 Risk Statements
4.1 Safety Statements
4.1 Hazard Declaration
UN1170 - class 3 - PG 2 - Ethanol, solution
4.1 Safety Profile
Mildly toxic byingestion. An experimental teratogen.Experimental reproductive effects. Humanmutation data reported. When heated todecomposition it emits acrid smoke andirritating fumes.
4.2 Caution Statement
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235
4.2 WGK Germany
4.2 Safety

Hazard Codes:?ToxicT,?HarmfulXn
Risk Statements: 63?
R63:Possible risk of harm to the unborn child.
Safety Statements: 53-23-36/37/39-45-36/37?
S53:Avoid exposure - obtain special instructions before use.?
S23:Do not breathe vapour.?
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 the label whenever possible.)?
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 3
RTECS: VH6860000
F: 8-10-23

4.3 Specification

?Vitamin A palmitate , its cas register number is 79-81-2. It also can be called?Retinol palmitate ; Retinol, hexadecanoate?; Retinyl palmitate ;?Retinol, all-trans-, palmitate ;?Optovit-A ; Retinol, palmitate, all-trans- .

4.4 Toxicity
LD50 (10 day) in mice, rats (mg/kg): 6060, 7910 orally (Kamm)

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H360 May damage fertility or the unborn child

H413 May cause long lasting harmful effects to aquatic life

Precautionary statement(s)

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P273 Avoid release to the environment.


P308+P313 IF exposed or concerned: Get medical advice/ attention.


P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


9. Other Information
9.0 Usage
Retinyl palmitate is a vitamin A analog that inhibits cell proliferation and induces cell differentiation. It is used as a dietary supplement as a lipophilic base for eg: soft gelatin capsule. Other applications include as pharmaceutical product which is used for manufacturing aqueous solutions using solubilizing agents such as cremophor. It is also used in the fortification of fatty foods such as margarine, spreads, oils, milk and dairy products. It is used in cosmetics for the preparation of creams and lotions.
9.1 Merck
9.2 BRN
9.3 Chemical Properties
95.0-100.5% Absorbance @325 nm ≥0.85%
9.4 Uses
9.5 Uses
all-trans-Retinyl Palmitate is an ester derivative of Retinol (R252000). all-trans-Retinyl Palmitate is used as a vitamin supplement in the treatment of Vitamin A deficiency. all-trans-Retinyl Palmita te is used as an antioxidant and a source of vitamin A added to low fat milk and other dairy products. all-trans-Retinyl Palmitate is also a constituent of some topically applied skin care products
9.6 Uses
retinyl palmitate 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.
9.7 Uses
vitamin A palmitate is known as a skin “normalizer.” It acts as an antikeratinizing agent, helping the skin stay soft and plump, and improving its water-barrier properties. Because of its impact on the skin’s water-barrier properties, it is useful against dryness, heat, and pollution. It is also an anti-oxidant and is suggested for use in sunscreens. Clinical studies with vitamin A palmitate indicate a significant change in skin composition, with increases in collagen, DnA, skin thickness, and elasticity. Vitamin A palmitate’s stability is superior to retinol.
9.8 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.
9.9 Mesh
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)
9.10 Mesh Entry Terms
Chocola A
9.11 Manufacturing Info
Retinol, hexadecanoate: ACTIVE
9.12 Use Classification
Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]|Cosmetics -> Skin conditioning
10. Computational chemical data
  • Molecular Weight: 524.8604g/mol
  • Molecular Formula: C36H60O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 524.45933115
  • Monoisotopic Mass: 524.45933115
  • Complexity: 803
  • Rotatable Bond Count: 21
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 26.3
  • Heavy Atom Count: 38
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 4
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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12. Realated Product Infomation