17772

Retinol

≥95.0% (HPLC), ~2700 U/mg

• 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/REAXYS Number: 403040
• EC Number: 200-683-7
• MDL number: MFCD00001552
• UNSPSC Code: 12352205
• eCl@ss: 34058018
• PubChem Substance ID: 329751561
• NACRES: NA.79

Properties

• biological source: synthetic
• Quality Level: 100
• assay: ≥95.0% (HPLC)
• form: (Powder or Crystal with Lumps)
• specific activity: ~2700 U/mg
• color: yellow to dark yellow
• 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

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain. Retinol is biologically active in a wide range of processes.

Retinol or all-trans-retinol is a 20-carbon molecule with cyclohexenyl ring, a side chain with four double bonds (all in trans configuration) and an alcohol end group.

Application

Retinol has been used as a standard in ultra-performance liquid chromatography - tandem mass spectrometer (UPLC-MS/MS) for the vitamins detection and quantification.

Biochem/physiol Actions

Retinol and its derivatives exhibit anti-aging properties. Retinol is used for treating wrinkles and signs of aging. However, due to its photo instability and skin irritation potency, it is hardly used in cosmetic formulations. Retinol is also used as a therapeutic for dermatoses. Its deficiency leads to xerosis and follicular hyperkeratosis.

Unit Definition

1 U corresponds to 1 international U acc. to Ph Eur II, 217 (1983)

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H317,H319,H360FD,H413
• pcodes: 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: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 1
• ppe: dust mask type N95 (US), Eyeshields, Gloves