R3375

Retinyl palmitate

Type IV, ~1,800,000 USP units/g, oil

• Synonym(s): Vitamin A palmitate, all−trans−Retinol palmitate
• Empirical Formula (Hill Notation): C₃₆H₆₀O₂
• CAS Number: 79-81-2
• Molecular Weight: 524.86
• UNSPSC Code: 12352205
• NACRES: NA.79
• PubChem Substance ID: 24899361
• EC Number: 201-228-5
• Beilstein/REAXYS Number: 1917366
• MDL number: MFCD00019414

Properties

• Product Name: Retinyl palmitate, Type IV, ~1,800,000 USP units/g, oil
• InChI key: VYGQUTWHTHXGQB-FFHKNEKCSA-N
• InChI: 1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+
• SMILES string: CC1=C(/C=C/C(C)=C/C=C/C(C)=C/COC(CCCCCCCCCCCCCCC)=O)C(C)(C)CCC1
• biological source: synthetic (organic)
• type: Type IV
• assay: ≥90% (HPLC)
• form: oil
• specific activity: ~1,800,000 USP units/g
• color: yellow to orange
• mp: 26 °C
• storage temp.: 2-8°C
• Quality Level: 100

Description

Application

Retinyl palmitate has been used as:

• a retinoid derivative to modulate expression of connexin Cx26 and Cx30 in the cochlea[1]
• a standard in high performance liquid chromatography(HPLC)
• as a retinoid substrate in the isomerase assay of eyecup protein homogenates[2]

Biochem/physiol Actions

Retinoids are ligands to nuclear receptors and have antioxidant functionality.[3] Retinyl palmitate is widely used in pharmaceutical and cosmetic applications.[4] In sunscreen, it protects from UVB-induced DNA damage and apoptosis.[5] Retinyl palmitate is used to treat photoaging in skincare cosmetics.[4] Retinyl palmitate is an effective chemopreventive agent to treat lung cancer.[6] It also regulates various biological processes including cell differentiation and proliferation.[4]

Review: Vitamin A metabolism.

General description

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A, respectively.[4] The retinoids comprise a cyclohexenyl ring with a 20-carbon with double bonds in cis and trans configuration.[4] Retinyl palmitate is a major storage form of vitamin A. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed.[7] Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate.[4]

Packaging

Sealed ampule.

Physical form

Oil at room temperature

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H360D,H412
• pcodes: P202 - P273 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Aquatic Chronic 3 - Repr. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 2
• flash_point_f: No data available
• flash_point_c: No data available
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter