EMAIL THIS PAGE TO A FRIEND
R3375 Sigma-Aldrich

Retinyl palmitate

Type IV, ~1,800,000 USP units/g, oil

Synonym: Vitamin A palmitate, all−trans−Retinol palmitate

  • CAS Number 79-81-2

  • Empirical Formula (Hill Notation) C36H60O2

  • Molecular Weight 524.86

  •  Beilstein/REAXYS Number 1917366

  •  EC Number 201-228-5

  •  MDL number MFCD00019414

  •  PubChem Substance ID 24899361

  •  NACRES NA.79

Purchase

Properties

Related Categories Biochemicals and Reagents, Vitamin A, Vitamins More...
biological source   synthetic (organic)
type   Type IV
assay   ≥90% (HPLC)
form   oil
contains   1-5% butylated hydroxytoluene as antioxidant
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

Description

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 vaccine adjuvant for recombinant HIV-1BaLgp120 administration,
• 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

Packaging

1, 5, 100 g in ampule

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

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
Flash Point(F) 
381.2 °F - closed cup
Flash Point(C) 
194 °C - closed cup

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number
Protocols & Articles

Articles

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apopt...
BioFiles 2008, 3.9, 12.
Keywords: Apoptosis, Cancer, Cell proliferation, Cellular processes, Chromatin immunoprecipitation, Condensations, Degradations, Diseases, Gene expression, Hormones, Immunoprecipitation, Ligands, Metabolism, Oxidations, Phosphorylations, Polymerase chain reaction, Sequences, Teratogens, Transcription, Type, Ubiquitinations, Usage, Vitamins

Peer-Reviewed Papers
15

References

Related Products

related product

Product #

Description

Add to Cart

08168 Timestrip Plus 8 °C

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?