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17772

Sigma-Aldrich

Retinol

≥95.0% (HPLC), ~2700 U/mg

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:
Molecular Weight:
286.45
Beilstein:
403040
EC Number:
MDL number:
eCl@ss:
34058018
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic

assay

≥95.0% (HPLC)

form

powder or crystals

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

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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)

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

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

Certificate of Analysis

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Certificate of Origin

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