R7632

Retinol

synthetic, ≥95% (HPLC), (Powder or Powder with Lumps)

• Synonym(s): Axerophthol, Vitamin A, Vitamin A alcohol, Vitamin A₁, 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
• UNSPSC Code: 12352205
• eCl@ss: 34058018
• PubChem Substance ID: 24899395
• NACRES: NA.79

Properties

• biological source: synthetic
• Assay: ≥95% (HPLC)
• form: (Powder or Powder with Lumps)
• specific activity: ~2700 U/mg
• technique(s): HPLC: suitable
• color: yellow to very dark yellow, to Very Dark Orange
• mp: 61-63 °C (lit.)
• 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.[1]

Application

Retinol has been used:

• for the synthesis of all-trans-retinoic acid in HepG2 cells[2]
• to study the effect of retinol on the growth of murine normal colonic cells cultured as organoids[3]
• as a standard for determination of vitamin A in cells[4]
• as a component of chemically defined medium for testis organ culture and spermatogenesis in vitro.[5]

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.[6] Retinol is used in the treatment of dermatoses including photoaging. Its deficiency is associated with the development of xerosis and follicular hyperkeratosis.[1]

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.[7]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Light protecting glass vial.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H317,H319,H360FD,H413
• Precautionary Statements: P202 - 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: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves