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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C20H30O
CAS Number:
68-26-8
Molecular Weight:
286.45
NACRES:
NA.79
PubChem Substance ID:
329751561
eCl@ss:
34058018
UNSPSC Code:
12352205
EC Number:
200-683-7
MDL number:
MFCD00001552
Beilstein/REAXYS Number:
403040

Product Name

Retinol, ≥95.0% (HPLC), ~2700 U/mg

InChI key

FPIPGXGPPPQFEQ-OVSJKPMPSA-N

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+

SMILES string

CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/CO)=C(C)CCC1

biological source

synthetic

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

Quality Level

100

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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.

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.

Other Notes

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

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

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9151
BCCL0766
BCCL4157
BCCH8320
BCCH0024

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Effects of dietary lead exposure on vitamin levels in great tit nestlings-An experimental manipulation
Ruiz S, et al.
Environmental Pollution (Barking, Essex : 1987), 213(2), 688-697 (2016)
S P Spencer et al.
Science (New York, N.Y.), 343(6169), 432-437 (2014-01-25)
How the immune system adapts to malnutrition to sustain immunity at barrier surfaces, such as the intestine, remains unclear. Vitamin A deficiency is one of the most common micronutrient deficiencies and is associated with profound defects in adaptive immunity. Here
K R Norum et al.
The American journal of clinical nutrition, 56(4), 735-744 (1992-10-01)
We discuss vitamin A with emphasis on its absorption, transport, cellular uptake, storage, and intracellular metabolism. Dietary retinyl esters are hydrolyzed to retinol in the intestinal lumen before absorption by enterocytes. Carotenoids are absorbed and then partially converted to retinol
Jacqueline A Jumpsen et al.
Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society, 5(2), 77-84 (2006-03-02)
The objective of this study was to investigate the effect of docosahexaenoic acid (DHA) supplementation on blood and intestinal DHA levels and lung function in mild/moderately affected adult CF patients with the DeltaF508 genotype. Cystic Fibrosis (CF) patients often present
Retinoids in the treatment of skin aging: an overview of clinical efficacy and safety
Mukherjee S, et al.
Clinical Interventions in Aging, 1(4), 327-327 (2006)
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