R3375

Retinyl palmitate

Type IV, ~1,800,000 USP units/g, oil

• Sinónimos: Vitamin A palmitate, all−trans−Retinol palmitate
• Fórmula empírica (notación de Hill): C₃₆H₆₀O₂
• Número de CAS: 79-81-2
• Peso molecular: 524.86
• Beilstein/REAXYS Number: 1917366
• EC Number: 201-228-5
• MDL number: MFCD00019414
• UNSPSC Code: 12352205
• PubChem Substance ID: 24899361
• NACRES: NA.79

Propiedades

• 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
• SMILES string: CC1=C(/C=C/C(C)=C/C=C/C(C)=C/COC(CCCCCCCCCCCCCCC)=O)C(C)(C)CCC1
• 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+
• InChI key: VYGQUTWHTHXGQB-FFHKNEKCSA-N

Descripción

General description

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A, respectively. The retinoids comprise a cyclohexenyl ring with a 20-carbon with double bonds in cis and trans configuration. 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. Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate.

Application

Retinyl palmitate has been used as:

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

Biochem/physiol Actions

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

Review: Vitamin A metabolism.

Packaging

Sealed ampule.

Physical form

Oil at room temperature

Información de seguridad

• 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_germany: WGK 2
• flash_point_f: No data available
• flash_point_c: No data available
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter