R7632

Retinol

synthetic, ≥95% (HPLC), crystalline

• Synonym(s): Axerophthol, Vitamin A alcohol, Vitamin A₁, Vitamin A, all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
• Empirical Formula (Hill Notation): C₂₀H₃₀O
• CAS Number: 68-26-8
• Molecular Weight: 286.45
• Beilstein: 403040
• EC Number: 200-683-7
• MDL number: MFCD00001552
• eCl@ss: 34058018
• PubChem Substance ID: 24899395
• NACRES: NA.79

Properties

• Quality Level: 200
• biological source: synthetic
• assay: ≥95% (HPLC)
• form: crystalline
• technique(s): HPLC: suitable
• color: faint yellow to very dark yellow
• mp: 61-63 °C (lit.)
• ε (extinction coefficient): 2700 u/mg at 326 nm in isopropanol
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/CO)=C(C)CCC1
• InChI: 1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
• InChI key: FPIPGXGPPPQFEQ-OVSJKPMPSA-N

Description

General description

Retinol or vitamin A alcohol is the main circulating form of vitamin A. It is not biologically active. Retinol or all-trans-retinol is a 20-carbon molecule with cyclohexenyl ring, a side chain with four double bonds (in trans configuration), and an alcohol end group.

Application

Retinol has been used:

• for the synthesis of all-trans-retinoic acid in HepG2 cells
• to study the effect of retinol on the growth of murine normal colonic cells cultured as organoids
• as a standard for determination of vitamin A in cells
• as a component of chemically defined medium for testis organ culture and spermatogenesis in vitro.

Packaging

100, 250, 500 mg in ampule

1 g in ampule

Light protecting glass vial.

Bottomless glass bottle. Contents are inside inserted fused cone.

Biochem/physiol Actions

Retinol and its derivatives exhibit anti-aging properties. In addition, it also acts as an anti-wrinkle agent. However, due to its photoinstability and skin irritation potency, it is not widely used in cosmetic formulations. Retinol is used in the treatment of dermatoses including photoaging. Its deficiency is associated with the development of xerosis and follicular hyperkeratosis.

Retinol works as a precursor of active retinoids. It is converted to retinaldehyde and subsequently to retinoic acid. All-trans and 9-cis-retinoic acid are the ligands for nuclear receptors, retinoic acid receptors (RARs) and retinoid X receptors (RXRs). These receptors are transcriptional regulators of various genes.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R7632.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety Information

• Pictograms: GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H317 - H319 - H360FD - H413
• Precautionary Statements: P201 - P273 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Aquatic Chronic 4 - Eye Irrit. 2 - Repr. 1B - Skin Sens. 1
• Storage Class Code: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves