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R1512

Sigma-Aldrich

Retinyl palmitate

potency: ≥1,700,000 USP units per g

Synonym(s):

Vitamin A palmitate, all−trans−Retinol palmitate

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About This Item

Empirical Formula (Hill Notation):
C36H60O2
CAS Number:
79-81-2
Molecular Weight:
524.86
Beilstein/REAXYS Number:
1917366
EC Number:
201-228-5
MDL number:
MFCD00019414
UNSPSC Code:
12352205
PubChem Substance ID:
24899347
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

200

form

solid or viscous liquid

potency

≥1,700,000 USP units per g

does not contain

antioxidant

color

yellow to yellow-green

mp

26 °C

storage temp.

2-8°C

SMILES string

CC1=C(/C=C/C(C)=C/C=C/C(C)=C/COC(CCCCCCCCCCCCCCC)=O)C(C)(C)CCC1

InChI

1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+

InChI key

VYGQUTWHTHXGQB-FFHKNEKCSA-N

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General description

Retinyl palmitate or vitamin A palmitate is a retinoid, which is an acid form of vitamin A. Retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain. Retinyl palmitate is a major storage form of vitamin A found in epidermis. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed.

Application

Retinyl palmitate has been used as a standard in high performance liquid chromatography (HPLC). It has also been used to study its effect on brain regeneration in larval Xenopus laevis.

Biochem/physiol Actions

Retinyl palmitate is widely used in pharmaceutical applications. It is also extensively used in cosmetic formulations due to its beneficial effects on the appearance of skin and anti-oxidant properties. Retinyl palmitate acts as a teratogen and affect vertebrate embryogenesis and regeneration. It is added as a source of vitamin A in low fat and skim milks. Retinyl palmitate acts as a chemopreventive or antineoplastic agent.
Review: Vitamin A metabolism.

Packaging

Sealed ampule.

Physical form

oil or solid

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Repr. 1B

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 2

flash_point_f

No data available

flash_point_c

No data available

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S D Todorov et al.
Meat science, 84(3), 334-343 (2010-04-09)
Bacteriocins bacST202Ch and bacST216Ch, produced by Lactobacillus plantarum strains isolated from Beloura and Chouriço, respectively, inhibited the growth of a number of Gram-positive and Gram-negative meat spoilage bacteria. According to trycine-SDS-PAGE, bacST202Ch and bacST216Ch are approximately 3.5 and 10.0 kDa
Fundamentals of Dairy Chemistry (2012)
The effect of retinyl-palmitate on brain regeneration of larval Xenopus laevis
Bernardini S, et al.
Italian Journal of Zoology, 77(3), 261-271 (2010)
Anticancer activity and mechanism of action of retinoids in oral and pharyngeal cancer
Klaassen I and Braakhuis BJM
Oral Oncology, 38(6) (2002)
Characterization of esterase and alcohol dehydrogenase activity in skin. Metabolism of retinyl palmitate to retinol (vitamin A) during percutaneous absorption
Boehnlein J, et al.
Pharmaceutical Research, 11(8), 1155-1159 (1994)
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